- "There seems to be some confusion. My name is Oswald Cobblepot. Many of you, no doubt, will have heard of me. Some of you, clearly, have not. For those poor, ignorant souls, I offer illumination. I am not a man to be trifled with. No. I am powerful. I am vicious. I'm King of Gotham."
- —Oswald Cobblepot[src]
Oswald Chesterfield Cobblepot (born Oswald Chesterfield Kapelput), known as "Penguin" to most, was born to Gertrud Kapelput and Elijah Van Dahl but his mother cut off contact with his father before his birth, due to the dislike his father's parents had for his mother's relationship with their son.
Oswald started out as a low level member of Gotham’s criminal Underworld, but through his cunning and manipulative skills, he eventually managed to take power and become the kingpin of Gotham. He lost his power after being driven underground by Theo Galavan and later was sent to Arkham where he was rehabilitated and reunited with his long lost father until his stepfamily killed him and abused Oswald to the point where he had a psychotic break and then killed them.
Oswald ran for mayor, and fell in love with his friend Edward Nygma. He murdered Edward’s girlfriend Isabella, and was shot by him. Oswald survived and was cared for by Ivy Pepper, who helped him build an army to retake Gotham. After reclaiming his power, he was eventually betrayed by Victor Zsasz and sent back to Arkham. Oswald escaped and took his revenge on Tabitha Galavan for killing his mother by murdering Butch Gilzean, and then killed Tabitha herself a month later. He would attempt to flee Gotham with Edward, but they both decided to join forces with the Gotham City Police Department to combat the Delta Force and was imprisoned a few months later. Ten years later, he tried to get revenge on Jim Gordon for his incarceration, but was captured alongside Nygma by Batman, a vigilante they have vowed not to let take over their city.
- "Every night when I was young, my mother would sing that song to me when I was going to bed. And every time, she would tell me... "Oswald, don't listen to the other children. You're handsome and clever and some day you will be a great man." She said that every time. That's all I have left now. Memories. And they're like daggers in my heart."
- —Oswald Cobblepot to Edward Nygma[src]
Born as the son of Gertrud Kapelput and Elijah Van Dahl, who had a secret relationship during the time Gertrud worked as a cook for the Van Dahl family. Elijah's parents forbade this relationship between their son and one of their servants. Despite Elijah standing up to his parents, Gertrud was already gone, without even telling him she was pregnant. Oswald Cobblepot was then raised solely by his mother in Gotham City and was told his father died when he was young. His mother often used to cook her special goulash for the young Oswald, an old family recipe she brought from Budapest. It is implied that Oswald was bullied as a child from a statement "Oswald, don't listen to the other children" which he said his mother said to him. She used to sing to him at night and tell him that some day he would be a great man, developing his desires for power and to move up in the world.
He eventually entered the criminal underworld through Carmine Falcone's underboss Fish Mooney and her gang, where he was hired as her personal umbrella-man. He also received the nickname "Penguin" from the other gangsters, which Oswald despised. Even though she treated him harshly very often, Fish actually appreciated Cobbelpot, thinking of him as if he were her son. However, he got tired of carrying out lower tasks at Fish Mooney's nightclub and therefore took advantage of his inconspicuous position as a lackey in order to study how Gotham's criminal underworld works. Cobblepot noticed Fish Mooney's desire to replace Don Falcone as the head of Gotham's mob, whom she considered too old and weak for the task. Oswald realized his potential and then started to forge a plan to play the city's mob bosses off against each other.
Ambition of a Traitor
- "There is a war coming, a terrible war. Falcone is losing his grip and his rivals are hungry. There will be chaos, rivers of blood in the street. I know it. I can see it coming."
- —Oswald Cobblepot to Jim Gordon[src]
Two months before the death of Thomas and Martha Wayne, Oswald was acting the part of a freelance informant, offering to sell information to his acquaintances. One of these acquaintances was the former GCPD officer and current Private Investigator Frank Collins.
Oswald Cobblepot was tired of being a lackey of Fish Mooney. He quickly sold her out to Crispus Allen and Renee Montoya of his own free will. Fish soon finds out and severely injures Cobblepot. After his assault by Fish, Falcone met him after saving James Gordon and Harvey Bullock and made a deal with him: in exchange for a secret he has, Falcone would assign Gordon to kill Cobblepot in hopes of persuading the detective into sparing him with the knowledge he was one of the few police officers with a moral compass, he would return to Gotham in secret and work his way into Maroni's grace as a snitch. Falcone agreed and asked for the secret Cobblepot has: Fish and Nikolai are secret lovers with plans to overthrow Falcone. Fish was supportive of Nikolai only so she could then take the position from him, and become the Queen of Gotham. James Gordon is then assigned by Carmine Falcone to dispose of the traitor. Gordon tricks Harvey Bullock by pretending to kill Cobblepot, who drops into the Gotham River. He resurfaces once the cops are gone, however, and proceeds to murder a fisherman for his sandwich in a crazed rage of hunger. He then sets out to create his own criminal empire.
Later, he was in the countryside after walking for a while, and he attempts to hitch-hike his way back to Gotham City. He is picked up by two men in an SUV, and is grateful for their help. However, they make fun of him and ask him if anyone has ever told him that he walked like a penguin; infuriated, Cobblepot broke a beer bottle and stabbed the man in the passenger seat before taking over the SUV. Hiding the body in a garbage bag, Cobblepot drove to a small trailer park and rented a small trailer for $100. He attempts to call the surviving boy's mother to get $10,000 in exchange for his release, but she does not believe him, and he, in turn, confronts the hostage once she hangs up. While it is not certain of this hostage's future, it is safe to assume his death.
- "It was my own fault. Foolish arrogance led me astray. But I learned my lessons. I'll be back, stronger and smarter than ever."
- —Oswald Cobblepot[src]
Oswald later arrived back in Gotham via bus. While waiting at a street corner he was recognized by a thug, who sought to capture and take him to Fish Mooney. As the man dragged him through a tunnel, Cobblepot disabled and murdered him with a pocket knife, took his money and used it to buy himself a tuna sandwich. He later took a job at a restaurant where he met and befriended Sal Maroni. He later made a surprise visit to Gordon.
Gordon angrily confronted him on returning to Gotham and putting him, his fiancé and Oswald at risk but reluctantly takes Cobblepot on as an informant when he tells Gordon about an upcoming gang war involving Arkham Asylum, and gives him information that helps him thwart an assassination attempt on Mayor Aubrey James. Cobblepot hires a gang of thugs to rob the restaurant so he can save the restaurant's money and endear himself to Maroni. Sure enough, Maroni promotes him to restaurant manager after the original restaurant manager was killed during the robbery. Cobblepot later visits the thugs he hired and kills them with poisoned cannoli. After their deaths, Oswald left with the money.
Sal Maroni makes plans to rob a casino owned by Carmine Falcone. Carmine Falcone meets with the mob leaders on his side to detail about what to do with Sal Maroni. Sal Maroni later watches the news of the "Viper" drug where he thinks that they might be of good use. Oswald tells Sal Maroni that he knows the janitor there that might be of help to them. Sal Maroni claims that "Penguin" is a good name for him. Oswald reveals his real name and how he used to work for Fish Mooney until Carmine Falcone's men tried to kill him. Sal Maroni then pins Oswald's head to the table. Sal Maroni later sends his right-hand man to pick up James Gordon at the police station where Sal Maroni wants to see him about Oswald Cobblepot.
James Gordon is brought to Sal Maroni at his restaurant where he wants to get confirmation about Oswald's story about Carmine Falcone to determine who is telling the truth. Sal Maroni hears from Jim Gordon about his investigation on Thomas and Martha Wayne and how he covered up Oswald's death to fool Carmine Falcone, Fish Mooney, and the Gotham City Police Department. Sal Maroni sees that Oswald is right and spares his life while letting James Gordon go. Sal Maroni states to James Gordon to keep their meeting private and that he might call on him again. After James Gordon leaves, Sal Maroni plans to use Oswald Cobblepot in their fight against Carmine Falcone. Later that night, Oswald and Sal await their men to come back from their heist at the casino. Upon the heist being complete, Sal has Frankie drive off.
When he returns home, Oswald's mother continues to suspect he is involved with a woman. Denying this, Oswald does mention that he has made friends with James Gordon. He then takes a bath and converses with his mother while soaking in a clawfoot bathtub. Meanwhile, having been identified as the perpetrator in Oswald's murder, Gordon is arrested and brought back to the Gotham City Police Department where he protests his innocence and Harvey Bullock is also apprehended when he comes to his defense. Suddenly, Oswald arrives, which shocks everyone.
Cobblepot leads Maroni's men to a warehouse owned by Falcone's underling, Nikolai, killing him and his fellow operatives inside. Cobblepot then stabs Frankie Carbone with the help of two Maroni operatives which he brought them over to his side. Cobblepot then meets with Falcone, and a flashback reveals that Cobblepot offered to be Falcone's spy when he was caught informing on Mooney.
Oswald attempts to make amends with Fish by offering her a broach as a gift. She accepts the gift, but then stabs him in the arm with it to punish him for snitching on her, claiming that he "hasn't suffered enough". Oswald then kidnapped Timothy, the young man who replaced him as Fish's personal assistant. He pressured Timothy into spilling Fish's secrets, although Timothy had very little access to secret information. After finishing the interrogation, he ordered Timothy killed to preserve the peace between the mobs and then limped out of the room. Oswald later confronted Fish's spy, Liza, and threatened to tell Falcone that Liza was spying on him. He ultimately agreed not to, but left Liza with the knowledge that he knew her secret.
Oswald was later brought before Falcone, believing Maroni behind the attack on his money vault. Cobblepot states that Maroni didn't commit the armory robbery, as there is a mole working for someone else, possibly for Fish Mooney. When he sees Liza enter the room, he immediately has his answer but remains silent as Falcone assigns him to find the mole. Oswald later tells his driver that he's not ready to rat out Liza yet, labeling her a "time bomb.
In his time in Maroni's ranks, he's given power enough to extort the fishermen on the mob boss's turf but is arrested by the GCPD after trying to squeeze more protection money out of them. He is eventually bailed out by Maroni, who makes it clear that he initiated the arrest himself to remind Oswald of his reach and teach him a lesson about hubris.
While dining at a restaurant with Maroni and several other gangsters, Falcone called him and ordered him to go see him. But before he could so, Jack Buchinsky caused an electric shock that forced Maroni and the other gangsters (including Oswald) to go to the GCPD for protection. The Electrocutioner then orchestrated another electric shock, this time much more powerful. Before Buchinsky could kill Maroni and his gangsters, Gordon stopped him and Aaron Danzig. After the Electrocutioner problem was solved, The Penguin went to Falcone's place, where Carmine reveals that Fish "captured" Liza and in turn for her return to Falcone, Falcone must leave Gotham. Oswald changes the plan when he reveals that Liza is a mole, Falcone sends Victor Zsasz and some henchwomen to get rid of Fish's thugs, Falcone then captures Fish and Butch Gilzean.
Oswald then became a high-ranking member of Falcone's gang and changed the nightclub's name to Oswald's and pink neon fish was replaced by a blue neon umbrella. Oswald however, was faced by Fish and Butch who escaped Falcone's torturer, Bob. Before they could do something ugly, Zsasz arrived and captured Butch but Fish escaped. Oswald also helped Gordon when Gordon wanted Arnold Flass arrested for murder, he had Gabriel interrogate Derek Delaware for information. Gabe then gave the info to Gordon. 
Fish revealed to Maroni that Oswald was a spy for Falcone, because of that Maroni had Oswald and him taken to a trip in a shack owned by Maroni in the woods. Oswald attempted to kill Maroni, only to find that the gun had no bullets. Oswald was nearly killed by Maroni when the latter ordered Duffy to destroy a car with Oswald in. Duffy was coerced to release Oswald under the threat of Falcone killing him.
Penguin tried to convince Don Falcone of Maroni's threat to his life, however, Falcone continues to talk about the re-decoration of Fish Mooney's club, much to Oswald's frustration. Falcone then tells Penguin that he has decided to give the club to Penguin as a reward and that he would deal with Maroni. Later Penguin arrives at the GCPD to bring Detective Gordon and invitation to the grand re-opening of the nightclub, but he has an awkward encounter with Edward Nygma who attempted to give him a riddle to answer though he was dismissed. When Jim arrived, he turned down Oswald's offer of attending the nightclub and though Penguin offered to help him with his case, Gordon rejected the offer telling him he didn't want him coming to the GCPD again. Offended, Penguin tells Jim that he shouldn't treat him that way and that he'd one day soon he'd need his help. Later, Penguin was visited by Don Maroni, much to his surprise, there the Don makes his intentions clear to not hurt Penguin, due to a deal he made with Falcone. However he warns him that the second Falcone was out of the picture, so was he.
When a drunkard dared to boo his mother, Penguin viciously attacked him in front of everyone. Later, the club continued to tank under Penguin's management. Falcone sent Victor Zsasz with a solution to the problem. At Penguin's surprise, he brings Butch Gilzean, who spent two weeks being tortured by the Zsaz to break his will, and to help Penguin run the nightclub.
Penguin later begins to have trouble getting alcohol for the club after running out, as the booze was controlled by Maroni who hated him with a passion. That night, thanks to unexpected help from Butch Gilzean, Penguin manages to steal alcohol having police officers "confiscate it".
Gordon and Bullock visit's Oswald's to ask the Penguin for his help and he is pleased to assist them after Jim promises him a favor and five minutes alone with Loeb's files. Gordon, Bullock, and Penguin reach an old farm located on the outskirts of the city where the Penguin had heard Falcone tell Loeb on the phone, that the farm was safe. There they are welcomed in by an elderly named Jude and Marge, under the guise of being a security team sent to check out the farm's security. Unexpectedly, the elderly couple, having figured out that they were not who they claimed to be, opened fire against them however they managed to subdue them quickly, leaving Penguin to watch them while they checked the attic. Later, the elderly couple managed to escape Penguin. Oswald later met with Marge and Jude after letting them go the previous day, with the promise of helping them escape the wrath of the commissioner. Unfortunately for them, he could only procure one ticket to Arizona, and gave the two the ultimatum of deciding who would get it. Marge strangles Judge, and afterward, Penguin shoots her with a shotgun. 
After being freed from Maroni, The Penguin plotted the assassination of the Italian Crime Lord in a bar called Lidia's. Oswald then convinced Lidia to hand over the bar to him while she still tending to the bar. Oswald hired the hired killer Connor to kill Maroni, he had Butch hide some guns at the bar after Butch was brainwashed by Zsasz.
When Maroni, his hitman Tommy Bones and some other gangsters were eating at Lidia's, Connor arrived and attempted to shoot Maroni, but found out that his gun had no bullets. Maroni's men then killed Connor. Oswald revealed that it was intentional as he wanted Maroni and Falcone to kill each other so he could take over. The first step of his plan worked and a bloody war began.
Cobblepot then attempted to murder Falcone at the hospital, but Falcone was saved by Gordon, who in turn saved both Cobblepot and Falcone's lives by killing Maroni's hit men. Gordon, Bullock, Falcone, Gilzean and Oswald then went to an old warehouse owned by Carmine, Falcone claimed that everyone who knew about the warehouse were dead. He was wrong, Fish knew about it and she was surely alive. She had arrived in Gotham just as the war reached its ending point. Fish overwhelmed them and tied them. She then called Maroni to make a deal. After Maroni offended Fish, she shot Maroni in the forehead, killing him instantly. A shootout ensued and Fish eventually won. The Penguin was however freed by Butch during the skirmish. When Fish was talking to the captives, Oswald arrived with a war machine gun and massacred all of Fish's thugs, finishing the last thug with a pistol. Falcone revealed to Jim and Harvey that he had retired. Penguin eventually found Fish in the rooftop and fought her. While they were fighting, Gilzean shot both in the legs, The Penguin then knocked Butch out and punched Fish, eventually pushing her into the river, killing his nemesis once and for all. He then climbed on a wall and shouted "I'm the king of Gotham!" into the night.
King of Gotham
The Penguin then began the life as a crime lord kingpin, collecting debts. Oh so around this time he adopted Selina Kyle as his personal assistant. After Gordon was discharged of service by Loeb, the Penguin said that he would convince Loeb to reintegrate him if he collected a debt from Odgen Barker, whom owed money to Falcone's former organization now Penguins who Jim killed in the process. He then intimidated Loeb to reintegrate him threatening his life. He later appears with several of his thugs gahtered in his main hall drinking, Harvey Bullock walks in. Bullock says that he will always be seen as Fish's umbrella man and that he wants revenge for Fish's death. Bullock is then held at gunpoint by Oswald's bodyguards and exits the room. Oswald angrily smashes his glass, but quickly calms down and asks for another drink.Oswald was forced by Theo Galavan to carry out acts out of his interest for him by holding his mother in captivity. Oswald and Butch murdered Janice Caulfield and he had Zsasz murder Randall Hobbs, though Zsasz was intercepted by the GCPD managing to escape and failed. He was later confronted by Gordon, who knew about the murders. Oswald said that Gordon had dirt on his name, since he collected a debt for him and killed an innocent man. 
After Penguin killed Janice Caulfield and failed to kill Hobbs, he returns to Galavan and asks for his mother's release, stating that he would still do Galavan's bidding. Theo denies and tells him to leave. Penguin is now determined to take down Galavan and get revenge on him. Butch advises him to kidnap Tabitha and trade her for Cobblepot's mother but Penguin doubts that Theo loves Tabitha as much as Penguin loves his mother. Theo later sends Tabitha to Cobblepot to give him a list of multiple buildings owned by Wayne Enterprises which Theo wants burned down. Theo also wants Cobblepot to steal an old knife out of a safe in one of the buildings. He arranges for Cobblepot to receive Bunderslaw's eye which is needed to open the safe. Penguin is able to get the knife and burn down the buildings. However, as he plans to find out what drives Theo in order to destroy him Penguin meets Edwige, an old associate of Butch to find out the history of the knife. Edwige tells him that the knife is the Wayne Family Crest which was used 200 years ago by an ancestor of Bruce Wayne to cut off the hand of Caleb Dumas after the latter was accused of raping Celestine Wayne. The angered Waynes forced Dumas and his entire family into exile where the Dumas changed their name to Galavan. Penguin learns that Theo is a descendant of the Dumas and wants revenge on the Waynes. Penguin is glad because this means Theo is driven by emotion and thereby vulnerable. He then plans for Butch to seemingly change sides, claiming that Cobblepot is too mad to serve, and get into Galavan's business, but in reality plans for Butch to search for Oswald's mother. To not give Theo the opportunity to doubt Butch's story, Penguin cuts off one of his hands.
Not knowing of Butch being reprogrammed by Tabitha, Theo sent Butch back to Cobblepot as a double agent and set a trap for him. Butch tells Cobblepot of his mother's location, and Cobblepot goes to the spot with his henchman, only to be confronted by Theo and Tabitha. Cobblepot orders Butch to shoot Theo and Tabitha only to be betrayed by him. Cobblepot then pleas for mercy, asking Theo to let his mother go and he will die in her place instead. Tabitha lets Cobblepot's mother leave, only to throw a knife at her in the back. Cobblepot breaks down at his mother's fate as a taunting Theo approaches him and he remarks that he never does the dirty work himself, tricking Theo to get close enough for Cobblepot to voice his plan of killing him and stabbing him in the neck and escaping. Cobblepot later raids Theo's Mayor victory party with the rest of his men, only to be confronted by Jim and wounded by Tabitha.
Empire in Ruins
Cobblepot later encountered Nygma in a forest while Nygma was trying to bury his girlfriend's body. Cobblepot was hiding in an abandoned trailer in the forest and asked Nygma to help him before passing out from the previously inflicted gun shot by Tabitha.
When Oswald woke up, Nygma wanted to get some advice from Cobblepot for how to be a murderer, only to be rejected by Cobblepot who states that he is not interested in giving advice. Cobblepot lost his will to extract revenge or fight as he sees that he is the reason for his mother's death. Nygma suggests that love is a weakness and now that Cobblepot's mother is dead, and Kristin is dead, they are both free man with nothing to lose, making them powerful. This sparks Cobblepot's will again to recover and take revenge.
After failing to convict Theo for kidnapping Ex-Mayor James, Jim was kidnapped by policemen that Theo brided. Theo fought Jim in a duel and won, and told the policemen to kill Jim slowly. The policemen were then shot by Gabe after Theo left, and rescued by Cobblepot.
Cobblepot brought Jim to Nygma's place along with few men still siding with Cobblepot and they prepare to strike at Theo's apartment. Selina later joins the team and gave them a secret passage into the apartment. They busted into the place before Bruce is sacrificed by Father Creel. Later, Captain Barnes arrives to arrest Theo and stop Jim for doing anything stupid but was later knocked out by Cobblepot. Jim and Cobblepot later take Theo to the Southside Docks. Cobblepot beats Theo with a bat repeatedly, and Theo pleas to Jim for a swift death and Jim shoots him in response. Cobblepot puts an umbrella through Theo's throat afterward.
Sent to Arkham
- "I am not a man to be trifled with. I am powerful. I am vicious. I am the King of Gotham!"
- —Oswald Cobblepot in Arkham
After the death of Theo, Cobblepot is left with nobody and wanders the streets. He is later arrested by Barnes. Cobblepot confesses to the murder of Mayor Theo and claims no one else is involved so that Jim and Nygma will not be arrested as well. Cobblepot also claims that he is insane, which is why he killed the Mayor. He is later sent to Arkham Asylum and greeted by Hugo Strange. After a brief session with Dr. Strange, Cobblepot was told he will be treated with proper techniques, which the idea of it terrifies Cobblepot.
When Jim visited Arkham Asylum to set up a trap for Mr. Freeze, Cobblepot tells Jim that he needs to help Cobblepot to get out because they are doing terrible things to him. But Jim replies coldly that Cobblepot is insane, as he claimed, and so he needed treatment. This angered Cobblepot, causing him to yell out that Jim was the one who killed Theo as he is being dragged away.
After some therapy, Cobblepot turned a lot gentler, calmer, and lost all violence tenancy through only a small amount of sessions. He is declared sane again and is freed by Dr. Strange, who claims to have bigger plans for Cobblepot after his release.
While at his mother's grave, Oswald pays his respects before he met his long-lost father Elijah Van Dahl and both were shocked to connect. While at Elijah's house, Oswald learned that Gertrud used to work as a cook for Elijah's rich family where they had been forbidden to make love. Upon Oswald meeting his stepmother, Grace, and stepsiblings, Charles and Sasha, Elijah holds a toast to their family.
Oswald and Elijah start to bond, with Oswald telling him of his past and being accepted by him. Oswald learns Elijah is sick and that he has a hole in his heart that continues to get bigger. Oswald eventually gathers up the courage to tell Elijah about his violent past. Elijah tells Oswald his past doesn't matter. This comes as a complete shock to Grace and her children. Grace tries to get Sasha to seduce Oswald, but he rejects her advances. Elijah becomes really sick and doctors announce that his condition is getting worse. Elijah tells Oswald that they will have many more years together. Elijah announces he wants to rewrite his will and leave everything to Oswald. As Elijah and Oswald have a drink, Elijah collapses and starts foaming at the mouth. The wine is spilled, revealing there was acid in it.
After Elijah's death, the Van Dahl wish to do away with Oswald, however after Oswald begs them to let him stay, they decide to keep him around as a free maid, assuming that Oswald would commit suicide after the trauma he has experienced. So Oswald is allowed to stay and cooks and cleans after the Van Dahl's, who treat him poorly and insult his late mother. One day, Oswald comes across the decanter that contained the poison used to kill Elijah. This, coupled with his poor treatment and memories of Elijah's death, caused Oswald to awaken from the conditioning he received at Strange's hands at Arkham. No longer inhibited by Strange's conditioning, he murders Charles and Sasha offscreen.
That night, Oswald serves Grace a roast dinner. Grace inquires as to where Charles and Sasha are and asks Oswald to ring the dinner bell. Oswald replies that he doubts they would hear it. He then reveals he knows all about their plot to kill Elijah. He then draws a knife on Grace, who screams out for Charles and Sasha to help her. Oswald tells her they will not come. Grace asks where they are, to which Oswald implies they are the very meal she has on her dinner table. Oswald then kills Grace by stabbing her to death.
A day later, Oswald sits in the mansion watching a newscast in which Theo Galavan, now going by the name Azrael, drops into the frame. Oswald flashes a smile, which quickly contorts into one of rage before saying "Hello, old friend".
The next day, as he's getting dressed, Oswald declares that there is nowhere to hide for Galavan and that he's coming for him. He's later seen paying his respects to Tabitha, who's in critical condition after getting stabbed by Theo. Butch believes him to be there to murder Tabitha, to which Oswald replies that he does have reason to do so, as she's the one who stabbed his mother in the back, however, she's really not the person at fault, and that Galavan is, as Tabitha was just following his orders. Oswald states that he was affected by Galavan because he ordered his mother's death. Butch was affected by Galavan because Tabitha's life is on the line because of him, and of course, it's because of this that Tabitha herself was affected as well. Oswald proposes that the two of them reunite, if only for the purpose of killing Galavan. Butch agrees, and the two of them go to Wayne Manor, where Theo is seen attempting to kill Bruce Wayne, who is flanked by Alfred and Jim.
Oswald surprises them all, telling Gordon that he should know by now that bullets don't kill the monster in front of them, and says to Theo that his last umbrella was stuck in his throat, and he's thinking of shoving another somewhere else. Oswald then addresses Gordon once more, saying that one thing he learned dealing with Theo is that you always need the right tools. Butch then lifts an RPG launcher to his shoulder and fires a rocket at Theo, who dies instantly. With that, Oswald and Butch depart into the night.
"Nothing is impossible..."
- —Oswald Cobblepot and Fish Mooney meeting each other again.[src]
Oswald then decides to turn his attention to Strange, seeking revenge for what Strange did to him while in Arkham. At At South Burnside, he and Butch attack a bus which they believed contains Strange, only to discover that they were mistaken. Oswald is mortified to discover Fish Mooney, very much alive. It isn't really made clear if Fish uses her new power to render Oswald unconscious or if Oswald passes out from unbridled fear. Butch also catches a glimpse of Fish, and retreats with his men. Oswald remains unconscious as a homeless woman later opens the back door of the bus, ergo accidentally unleashing Strange's experiments into Gotham City.
Gaining public support
Being spared by Fish confused Oswald, causing him to go over the nights events over and over again in his head. Six months following the incident, he arrived at the police precinct during a press conference, accusing Nathaniel Barnes of lying to the people of Gotham. Oswald then told the reporters that he was present when the 'monsters' escaped Indian Hill, and urged them to find the main instigator, Fish Mooney. Once done, he crosses paths with Jim, who is now working as a bounty hunter, and points out his surprise that he hasn't found Fish yet. But Jim replies that Oswald hasn't made it worth his while, something in which Oswald agrees with.
He stops by the new nightclub run by Barbara Kean, known as The Sirens, where he made her an offer to protect it, but she turns him down. She is also in partnership with Tabitha whom Butch still has a crush on, causing Oswald to send him to the bar due to the awkwardness. He then tells the pair to spread the word that he wants Fish Mooney, and will pay a million dollars to whoever can bring her in: alive or dead. Oswald and Butch then depart, but not before Oswald reveals that Butch has been pickpocketed by Selina Kyle.
Oswald stops off at Arkham to visit Nygma, bringing him a gift which is said to be an almost unsolvable puzzle box, however Nygma solves it within seconds. Nygma apologises to Oswald for abandoning him months previously after his release from Arkham, but Oswald makes clear that he has forgiven him. Oswald talks about his troubles with Fish, but Nygma reminds him that "Penguins eat Fish".
After Barbara and Tabitha ran into some trouble with mobsters demanding protection, which lead to two of the mobsters being killed and the ringleader badly beaten by Barbara. It transpires that Butch is involved, as he hoped that Tabitha would run back to him for protection. Annoyed, Oswald shoots the last remaining mobster dead, and informs Tabitha that the only reason she is still alive is because of Butch, but once he gives the word he will kill her in retaliation for her killing his mother.
Oswald holds his own press conference, informing the people of Gotham that he has been warning the police about Hugo Strange's monsters and Fish Mooney, however they said that Fish wasn't real and saying that the escapees were victims that need their help. He tells them that despite the GCPD recently just trying to apprehend Mooney, she ended up escaping. Oswald tells them the city is being invaded by the monsters, and urges the people of Gotham to help kill every single monster, which results in him getting a round of applause and public support.
Back at his mansion, Oswald and Butch watch a news broadcast about a hostage situation at an old mansion lead by Fish. Gathering a crowd of people, they arrive at the mansion during a police standoff, much to the anger of Barnes, who states that Bullock and Gordon have been held hostage. During the chaos Oswald gets a phone call from Gordon who tells him that Fish is escaping into the woods with Hugo Strange. Pleased, Oswald orders the crowd to storm the mansion, before going off on his own. He confronts Fish and holds her at gunpoint, and demands to know why she allowed him to live. Fish explains that she couldn't kill Oswald, due to how much he had come along and that turned him from an umbrella boy to the terror of Gotham, from Oswald to the Penguin. Almost tearful, Oswald decides to spare her life and allow her and Strange to escape. He returns back to the crowd where they have killed two of the monsters and are burning them. Oswald is then lifted up in the air and hailed by the crowds, showing their full support for him.
Trusting with the newfound support by the people of Gotham Oswald decided to use his influence to run for Mayor of Gotham against Aubrey James, confident in his abilities his campaign gained a lot of support. Aubrey James reluctant to accept the fact the a criminal such as Penguin himself could win the election attempted to disuade him even threatening him to which Oswald replied by showing his own force holding him and his men at gunpoint but assured him he did not want to kill him as the election would be dull without an opponent although acknowledging he required some more assistance.
Blackmailing Arkham's head warden into releasing Edward Nygma into his custody, Oswald arrives at Arkham's gates to find Nygma unexpectedly awaiting his arrival. Continuing his campaign to become Mayor of Gotham, Oswald has Butch pay off numerous higher ups in order to secure his victory, much to Edward's suspicion and later his disapproval upon discovering it. Waiting for the news of the elections it is revealed by Butch that Nygma had been taking all the money back from the higher ups of Gotham and had cost him the election, threatening his life Edward drew his attention to the television revealing that in fact Oswald has won the election in a landslide, to which Edward said that he always believed in him. Oswald accused Butch of not truly believing in him, and appointed Edward as his chief of staff, much to Butch's anger and jealousy.
Mayor of Gotham
During a conference, Oswald unveiled a statue of his late mother. The conference was attacked by a new incarnation of the Red Hood Gang who shot up the statue and decapitated it. Angered, Oswald ordered his men to find the leader of the gang and bring him his head. During this meeting, Oswald mentioned he would be throwing a party at The Sirens. The location of the Red Hood was discovered and Oswald along with Edward, Victor Zsasz and a couple of other goons went to the location to deal with them, only to find Butch standing over their bullet-ridden bodies, having "dealt" with them. Pleased, Oswald holds another conference stating the Red Hood have been dealt with and congratulates Butch, whom he has now softened up to again. But secretly, Edward isn't certain things are what they seem.
At the Sirens nightclub, Oswald is greeted by Bruce, who thanks Oswald for saving him from Galavan. During the night Oswald is attacked by Butch who is donning the red hood mask, but it turns out his bullets were filled with blanks (as part of a setup between Edward and Zsasz). Zsasz shoots Butch in the back and Oswald berates him for his betrayal. Tabitha intervenes to rescue Butch, who proceeds to break free and attack Nygma nearly strangling him to death but Oswald then attacks Butch and knocks him out and has him brought into police custody. Later that night Oswald comforts Edward at his mansion and embraces him. Despite Butch's arrest, he escapes from his police escort with the help of Tabitha.
Oswald realizes he's fallen in love with Edward and reveals so to his housemaid that he plans to confess his feelings. Making attempts throughout the day to confess his love to no avail he finally builds up the courage to ask Nygma to discuss something over at the mansion that evening to which Ed agrees by offering to pick them up a bottle of wine. But this plan is scuppered the next morning after assuming Edward was kidnapped and tried to file a missing person report but was relieved when Edward arrives. However, Ed reveals he has met a woman named Isabella whom he claims he has fallen in love with.
Jealous, Oswald arrives at the library where Isabella works and drops that Edward was sent to Arkham for murder and killed his last girlfriend Kristin Kringle, whom Isabella has a strong likeness to. But this plan fails when Isabella accepts Ed's past and reveals she is not afraid of him with it, and kisses Edward at the mansion, much to Oswald's envy and frustration.
Oswald later on manipulated Ed into breaking it off with Isabella when he began to worry about her safety afraid he might hurt her as he did with Kristin and asked Oswald to do it for him by paying her a visit but to do it gently. Oswald arrived at Isabella's apartment and told her it was over between her and Nygma but she persisted she wasn't going to let him go which infuriated him leaving him to threaten her and leave with his final warning. Reporting back to Ed on the situation, knowing she would persist Oswald had Gabe cut her brake wires in secret anticipating her route and leading her to her death hurtling towards a passing train killing her.
The death of Isabella makes Ed distraught, seemingly doing nothing but mope about her death. While Oswald is getting his portrait painted, he tells Ed to try and get over her death by finding closure. Edward then goes to the railroad cross where Isabella died and discovered from a blind homeless man that he heard her screaming before the crash. Ed takes matters into his own hands and goes to the repair shop where Isabella's car has been towed and discovers the cut brake wires.
He storms into the mansion carrying the brake wires to Oswald. Before Ed has a chance to say anything, he shows Ed his portrait and that he was included in the background. Edward goes on to tell Oswald that he knows who cut the brake wires. Oswald tenses up and is visibly afraid for a moment before Ed concludes Butch did it to get revenge on him.
Barbara confronts Oswald over the location of Tabitha and Butch who have gone missing, although Oswald denies any knowledge of their whereabouts. In actuality they are being tortured by Edward, who believes that Butch is responsible for killing Isabella. However he ends up sparing them when he comes to realization that Butch wasn't responsible, although Tabitha ends up losing a hand in the process during the torture session. Not long before this, Barbara finds out from Oswald's maid that Penguin was the one who killed Isabella and planned to use this weakness against Oswald so she could take control of Penguin's empire.
Edward begins to suspect that Oswald is responsible for killing Isabella after Barbara informs him that Penguin is in love with him. Edward tricks Oswald into making it clear he is in love with Edward, causing Edward to leave. Edward then quits his role as chief of staff, much to Oswald's devastation who - despite not able to be officially Edward's lover - still wanted to remain his best friend. After Edward leaves Oswald, he secretly plots his downfall with Barbara, Butch and Tabitha, with the plan to make Oswald suffer terribly before his death. Seemingly being abandoned by Nygma, Oswald under worry for his whereabouts began to lose focus as Mayor and his reluctance to rely on Edwards replacement. After seemingly seeing his father appear to him as an apparition he was informed that his father's remains were stolen.
Finding them hidden in his office closet Oswald suspects Edwards replacement and bludgeons him to death in his office, leaving him nervous during an interview for fear they discover he is still a murderer and ruin his reputation as mayor, once again his father's "spirit" appeared crossing the room and in a rush Oswald openly insults the people of Gotham on live television in an effort to speak with his father, not finding him anywhere in proximity he is having his reputation ruined by Nygma in secret.
Barbara attempts to comfort him by revealing that not only is he losing his grip as Mayor but also as Gotham's ruling crime-lord he needs to show his men that he has not been weakened by his mayoral status and still holds full control. Under Barbara's manipulation she has Tabitha threaten one of Oswald's most loyal underlings Tommy Bones into pretending they hold Nygma hostage are the ones who wish to take his power. After this Penguin vows vengeance against Bones and orders his men to find Nygma at all costs. But then receives a phone call from Nygma himself telling him his whereabouts.
When Oswald arrives with the little men he was able to spare Edward reveals himself by gunning down Oswald's men in front of him and having him tied to the remains of Isabella's car while waiting to have acid poured on him, pleading with Ed and claiming that he did it for love he is abandoned by him and left to die. Being released by a confused police officer Penguin returns to his mansion intent on contacting reinforcements and cementing what's left of his rule and find Ed but his cut short by the intrusion of Tabitha and Butch who take him to the Sirens where Barbara interrogates him on Nygma's whereabouts but to no avail as neither does Oswald know or care to tell them if he did as he realizes now that even after all that had been done to him by Ed's hand he still loved him. Edward reveals himself to have been listening all along, Penguin wishes Barbara luck at the head of the table and is dragged off to be killed.
On the docks Penguin makes his final plead against Ed only to once again be rejected, claiming that he was the one who made him into what he is and that Edward Nygma would be nothing without The Penguin but Edward reluctant to give in states that he loved Isabella and he killed her shooting him and pushing him into Gotham Bay watching as he sunk to the bottom.
Plans of Revenge
Oswald having barely survived the gunshot wound was found floating in Gotham River by Ivy Pepper who hid him and nursed him back to health over the course of a few weeks. Attempting to befriend him he rejects her and dismisses her obsession with plants as being a freak and has her contact any loyal remnants of his crew. Gabe arrives at the abandoned estate where Ivy had been hiding Penguin but Ivy sensed that he couldn't be trusted to which again Oswald dismissed her leaving her to run off by herself. Oswald is soon betrayed by Gabe and tied up to be auctioned off to the highest bidder and killed properly, Ivy is caught by one of Gabe's men and tied up alongside Oswald.
While Gabe and his men are distracted Ivy offers Penguin another chance to be nice to her to which he agrees, using her perfumed scent she has one of the men untie them and kill everyone apart from Gabe. Taking the gun he shoots the man and turns it on Gabe, having him carry the bodies he attempts to once again swear his allegiance to Penguin but under the influence of Ivy's perfume is shown to once again be lying stating that they had only followed him out of pure fear not respect referring to when he used to carry around an umbrella and being a freak himself causing Oswald to lose his temper and hack him into pieces with a gardening tool much to Ivy's amusement.
Oswald feeling dejected at the fact that without any loyal follows his plans of revenge will be short lived, to which Ivy offers to ally herself with him and help him retake Gotham with the help of the remaining "freaks" from Indian Hill causing himself to smile.
Their first stop was Victor Fries, who was living far off in an ice chamber in the snow to stay alive. At first he was mad at Oswald and threatened his life because he drove the other freaks out of Gotham, but Penguin convinced him that he only said that stuff because that's what the people wanted to hear, he would give him all the supplies he needed to free himself from his ice chamber once he had his power back, and he had his suit, Fries smiled implying that he accepted the offer.
Next, they tried to recruit Bridgit Pike, who was currently working at a blacksmith shop and was constantly being picked on by her boss and co-workers for being a freak. She turned the offer down as she thought that this place was bad but Gotham's worse, although Ivy convinces her that there's nothing wrong with being a freak. Penguin offers to kill her boss but she says,"nah", and kills him herself and tells him she quits.
They return to the mansion, where Bridgit and Victor meet again and are not happy about it so they point their guns at each other until Ivy reminds them that they're like a family. Penguin finds out on the news that Nygma is now going by The Riddler, and tells the rest to rest up for tomorrow.
Oswald visits Jim, with the information that Nygma was demanding information about The Court of Owls on television until Jim had arrested him but he escaped, but Oswald doesn't believe that Nygma escaped Jim's custody. Jim tells Oswald to let it go but Oswald still gives him his phone number and tells him to call him later. Jim calls him later and tells him where the location of a Talon and an Alice Tetch bomb are so he could talk with the Court about Ed, Oswald shows up and has Bridgit kill the Talon with her flamethrower but the bomb is about to go off so Jim leaves. Since they killed a Talon The Court had another Talon kidnap Oswald at his mansion and lock him up.
At War with Nygma
Oswald demands to speak to the person in charge until Edward, who is in the cell next to him, asks, "Oswald?", causing Oswald to try to grab him through the bars. Oswald eventually comes to the realization that being locked in cages does neither of them any good so they need to help each other escape agreeing to resume killing each other on the outside but with a 6 hour window.
Oswald meres up with Ivy again who is with Selina Kyle, and Ivy explains that when Oswald disappeared Victor and Bridgit assumed that he was wasn't coming back so they split up really frustrating Oswald and making him throw a bunch of breakables. Edward figures out where they are and him and Butch come in and Selina ditches them. However, Oswald has an escape route through a bookcase and him and Ivy escape while Tabitha knocks out Selina and brings her back to Sirens club.
In exchange for money to get out of town Selina calls Ivy, who was at the last safe house with Penguin, and asked her where they were. Ivy told her where they were and Penguin called her an idiot because he knew it was a setup. Ed, Barbara, Tabitha, and Butch found them but Nygma wouldn't kill Penguin until he calls him The Riddler. Eventually, Fish Mooney returns and takes Penguin for herself.
Forming an alliance together Fish and Penguin combined their forces with the ultimate goal to seize the antidote to the Tetch Virus in order to create a Gotham City for people like Penguin and all the freaks, via Hugo Strange whom Fish had captured once again, Penguin with the help of Mr. Freeze and Firefly tortured Hugo using the same device used on himself during his stay at Arkham Asylum causing him to reveal the location of the antidote he had hidden away. Arriving at the location and retrieving the antidotes they noticed Fish's men had been killed and were attacked by masked warriors causing a fire fight between them, Mr. Freeze and Firefly.
Interrupted by Jim Gordon and Harvey Bullock, Jim being infected with the Tetch Virus took out most of the masked men single handedly and accidentally killed Fish in the heat of the moment with a sword and destroying the antidote. With her dying breath, Fish tells a grieving Cobblepot that she had died too many times already and to either take Gotham for his own or burn it to the ground. Mooney's death then causes Penguin to lash out at Gordon. Jim almost choked Oswald to death until Harvey knocked Gordon out with his shotgun and took Penguin into his custody. Jim and Harvey had decided to hand Oswald over to Nygma in exchange for Jervis until Barbara, Tabitha and Butch came to get back Jervis which caused Nygma to throw a grenade at them and run away. As Nygma tried to leave the scene Oswald knocked him out and handcuffed him, using a police car to flee the scene.
When Nygma came to and realized he was handcuffed, Oswald told him he was not as smart as him and Nygma responded that Oswald's tendency to gloat was always one of his least attractive qualities and that he could never love someone like him as he behaved like a spoiled child who threw a tantrum whenever he did not get his own way. This led to Oswald drawing his gun and preparing to deal with Nygma, until the latter kicked the door open, having broken free of his handcuffs, and knocked Oswald to the ground. He grabbed the gun and pointed it at Oswald, leading the latter to rant that he was supposed to kill him this time and that when Nygma shot him that was the day he was reborn as the Riddler and that his entire persona was based on a lie, adding that there was nothing he could do about it but Nygma disagreed.
Nygma took him to the pier where he shot him and pointed his gun at him, asking if he had any last words but Oswald said that he was fine for now. Nygma said there would not be a later since he was going to kill him, which Oswald understood. However, when he tried to shoot him, no bullet came out which led Oswald to reveal that he removed them when he knocked Nygma out before summoning Ivy and Mr. Freeze. A shocked Nygma realized that Oswald had been playing him since he knew that Nygma would take him to that spot. Oswald revealed that Nygma had used his tie pin to remove his handcuffs as he wanted it to be personal and further added that he was predictable since he was driven by a desperate, compulsive need to complete what he started. When Nygma asked why he did not kill him, Oswald said that Nygma was the one time he let love weaken him and that he would be keeping him around as a constant reminder not to make the same mistake again, leading Mr. Freeze to turn him into an ice sculpture which Oswald later planned to use as the centerpiece of his newly founded club, The Iceberg Lounge.
- "You know, Augustus Caesar once presided over the longest period of peace and prosperity the world has ever known. It was called the Pax Romana. Perhaps, one day this will be known as the Pax Penguina."
- —Oswald Cobblepot to assembled press conference[src]
In the aftermath of the Tetch Virus outbreak, Oswald and his crime family played a major role in restoring order to the city, though their methods were controversial to say the least. Cobblepot and his men dealt with criminals with violence and deadly force, but did manage to cut the crime rate in half. The next step in Penguin's plan was to create a system of unionized crime by issuing "licenses of misconduct" that allowed only chosen criminals to commit crimes in exchange for a portion of their profits. Anyone who committed a crime without a license was dealt with using deadly force. Cobblepot even went so far as to legitimize this new arrangement by making a deal with the city government. He referred to his new regime as the "Pax Penguina."
While Cobblepot's enforcers were largely effective in maintaining the "Pax Penguina" one gang, led by a man named Merton, refused to bow down. They abducted Jonathan Crane from Gotham Asylum and forced him to recreate his father's fear-inducing formula. They employed the formula as a chemical weapon during one of their bank robberies and planned to use it to eliminate Cobblepot himself. However, Cobblepot had cleverly anticipated their actions and turned the tables on them when they came to kill him at the Iceberg Lounge. His plan was to execute them and solidify his power and reputation. But due to a betrayal by Ivy Pepper, the gang broke loose and Cobblepot was gassed with Crane's formula. The gas caused him to hallucinate a demonic Riddler and thus began screaming in terror and fear. His intense scream caused him to humiliate himself in front of the press, which led to a newspaper headline "Penguin or Chicken?" However, his hold over the city remained unbroken.
Following this incident, Oswald would confront Jim Gordon at the GCPD and made an offer with him: Penguin would let the GCPD operate but Jim either had to admit that Cobblepot was doing a better job at keeping the city safe than the GCPD was or he had to find Jonathan Crane and hand him over to Oswald. Jim chose to find Jonathan but Crane managed to escape which caused Oswald to acuse James of not keeping his end of the bargain however Jim argues that there was no deal. In his meantime, Oswald confronts Barbara about her new weapons business, which she planned to run with Tabitha Galavan and Selina Kyle, and agrees that Barbara could run the business but said that it had to be part of him and his criminal empire. He also looked into the suspicion of who was paying for her business as she had just lost her club and had been presumed dead for months.
During a visit at the Falcone Mansion, Penguin watched a news report on TV about the actions of his henchmen and the GCPD that tried to hunt down Professor Pyg in the Narrows. While Sofia spent time with some children from the Falcone Home and School for Orphans in the background of the same room, Oswald proudly pointed at the TV screen, explaining Falcone that these are his men led by Headhunter, who he was talking about before. He then noted that Headhunter is effective even though he is kind of a moron and remarked that technically his men saved a cop from the Pyg, cheerfully calling it great PR. While Cobblepot talked, a girl from the orphanage suddenly stepped in front of the TV screen and blocked the view, leading to Penguin asking her to go away. Due to him not being used to children around him, he acted quite confused and then simply picked the girl up and carried her aside, before sitting down again and asking the question if his alliance with the GCPD is not the most brilliant idea he ever had, noting that it is Pax Penguina taken to a whole other level. Only then did he realize that Sofia didn't even really listen to him talking about his genius plan since she was too busy with the children of her orphanage in the background.
Thereupon, she told him that he doesn't need to know what she thinks, resulting in Oswald to be even more interested in her view. To satisfy him, she orders the girl that interrupted Oswald a few moments before to hold her ears closed and then started to explain him that her father never would have allied with the GCPD since they are incompetent and unreliable. She moved on by predicting that they will fail big one day and he will fail with them. He afterwards sarcastically thanked her for her input and grabbed some food from the table next to him before explaining her that she has shown her very clearly what not to do, continuing by telling her that in fact he now wants to get even more involved on a personal level. However, Sofia thereon told him that he shouldn't ask for her opinion if he doesn't want to hear it anyway before allowing the girl to open her ears again and turning back to the children. Annoyed by their conversation, Oswald laid down the food and wanted to leave the room, but the girl now stood in his way once again, leading to him carrying her aside a second time. The Penguin and one of his henchmen he brought with him then left the Falcone Mansión.
Knowing about her true intention, Oswald payed Sofia a visit at her mansion, revealing towards her that he realized she was planning to destroy him from the very beginning. Sofia then showed her true face by congratulating Penguin for his realization in a sarcastic and vicious way, noting that Oswald was very easy to manipulate by simple things like a foot massage and goulash. On Penguin's orders, Victor Zsasz afterwards allowed the Dentist to enter the room, a torture expert hired to interrogate Sofia, with Cobblepot ironically explaining that he is not the kind of dentist who gives out lollipops after the visit. However, after Penguin and Zsasz left, Sofia threatened the Dentist that if he does not untie her, his wife and son will be killed by her henchmen as revenge. Fearing the death of his family, the Dentist eventually untied her, betraying Penguin.
At night, Sofia and the Sirens took Martin with them to meet Penguin under the Crown Point Bridge. Shortly after, Cobblepot's limousine appeared and Oswald walked out of the shadows with Victor Zsasz. To force him to hand over Gotham's underworld to her, Sofia threatened to kill Martin. After Penguin told her that her father Carmine will be disgusted when he learns his daughter threatened the life of a child, but Sofia replied that he will be proud of her instead. Cobblepot then moved on by sarcastically telling her that it must be hard to live her whole life trying to get her father's approval and he himself can not relate since his parents loved him without any conditions. Heavily provoked by this statement, Sofia threatened once more to kill Martin, and adds that she will then execute him.While obviously getting nervous, Oswald asked her to not kill the boy, since he is innocent and after he submitted, Sofia allowed Martin to go ahead towards Penguin. Thereupon, Cobblepot apologized for everything he said towards Martin and revealed that he indeed cares about him. He then sends Martin away to wait in the car. As soon as the boy reached the limousine Oswald's mood changed from touched to sadistic and vicious. He then turned to Sofia, lauding her for being wise enough to use Martin against her, but that he will not allow this to happen again. Penguin then pulled a detonator, causing the car to explode behind him and shocking Sofia. Immediately after, Victor Zsasz and Penguin's other allies began shooting at Falcone and the Sirens, who however managed to escape the attack. While his men were still shooting, Cobblepot shouting at them that if they wanted a war, they got one, before leaving the battlefield behind him.
When Sofia Falcone stated that Oswald Cobblepot killed Martin, Captain Gordon led the police into arresting Cobblepot at the Iceberg Lounge. Believing Penguin was responsible for Carmine Falcone's death, Victor Zsasz denied any knowledge of Martin's survival, whereon Oswald was arrested by the GCPD and dragged out of his nightclub. The police officers took him to the GCPD building where two cops took him to a prison cell in which various low-level thugs were already imprisoned. When they opened the gate, Penguin pulled himself out of the officer's grip and preferred to walk in the cell on his own with the little dignity that was still left. Vanessa Harper and Gordon stood on the podium at the Captain's office and watched as the prison cell door was shut in Cobblepot's face. Harper said "You did it, Cap. You won." and began to clap, whereon all the other GCPD officers also started to applaud at their new captain. Locked up with the regular henchmen, Penguin had to watch as the cops cheered for Gordon. Defeated and humiliated in front of all the people present, Oswald closed his eyes, realizing he had lost his power over Gotham's criminal underworld once again...
Second Arkham Incarceration
After he had been blamed by Sofia Falcone for the faked murder of Martin, Cobblepot was incarcerated at Arkham Asylum. While heavily ranting about Sofia, Jim Gordon and Victor Zsasz who betrayed him and caused his imprisonment, a voice from the adjacent cell greeted Penguin with the words "Hey, buddy". Even though Cobblepot ordered the other man not to talk to him, the fellow inmate moved on by explaining that this place is full of lunatics and he just thought they could help each other out. Realizing the voice came from the other side of a small grating near the ground, Cobblepot kneeled down to watch through the barred window that connected the two cells. After ironically asking the other prisoner how he could help him, the inmate claimed to be very resourceful before laughing amused afterwards. However, Penguin was immediately shocked since he recognized that insane laugh. Thereupon, the other inmate finally revealed himself through the grating and turned out to be Jerome Valeska himself. After offering Oswald to become his best friend, Jerome moreover asked Oswald to give him a smile before bursting out into maniacal laughter. 
- "Tell me something. You appear to have everyone here under your thumb. The guards, the inmates."
"What can I say? I'm a charismatic guy."
"You could escape anytime. Why stay?"
"Hmm. Why indeed?"
"You're planning something."
"Righty-o, old boy. Something spectacular. See, I'm in this funny farm 'cause I need to find the crÃ¨me de la crazy. Which is why I need you..."
- —Oswald Cobblepot and Jerome Valeska[src]
During a stormy night, thunder rumbled in Gotham City while Oswald was locked up inside his prison cell and wrote a letter to Edward Nygma. In front of his cell door, Jerome told an Arkham guard how he once strangled someone, whereon the door was unlocked and Penguin jumped up from his chair in horror. Valeska said "Relax, buddy." and entered the room before adding "You gave me what I needed. The laugh of the century". Jerome then clicked his tongue before plumping himself down in Oswald's bed and closing his eyes. Cobblepot said "Tell me something. You appear to have everyone here under your thumb. The guards, the inmates". Jerome whispered "What can I say? I'm a charismatic guy". Annoyed, Penguin asked him why he chooses to stay in Arkham when he could just escape anytime. When Jerome responded "Why indeed?", Oswald laughed and said "You're planning something". Valeska answered "Right To, old boy." and revealed that he is planning something spectacular. He added "See, I'm in this funny farm 'cause I need to find the crÃ¨me de la crazy." before he sat up in the bed and said "Which is why I need you".
Thereon, both villains bursted out into insane laughter and Jerome said "Ah, you get it. But when we're done, the world out there that'll be the asylum. What do you say?". Oswald smiled at Valeska and thanked him for the kind offer, but then sat down in front of his desk to continue penning his letter to Ed and told Jerome that he does not expect to be here very long. Behind Cobblepot, Jerome got up and sneaked up on him. Valeska softly grabbed Oswald's shoulders and spoke right into Penguin's ear. He said "You'll come around. They always do." before letting go of Oswald's shoulders. Jerome picked up some dirt from Cobblepot's prison uniform and dropped it on the floor, then turned around and started whistling while leaving the prison cell. Oswald watched as Jerome walked down the corridor and then said "Nope" when Valeska was far enough away so he couldn't hear it. Right then, an inmate collecting letters from all the prisoners came to the cell, whereon Penguin got up from his chair, sealed his letter and added it to the pile of other letters already collected.
- "I see the other you. The one whose name I wouldn't speak. But because he has earned it and because I need him, I'm saying now: I need you...Riddler..."
- —Oswald Cobblepot to Edward Nygma, causing the Riddler to finally break free[src]
When Nygma went to Arkham Asylum to get himself imprisoned there, the Riddler started to appear in his hallucinations again and asked the riddle 'What has two eyes but can't see'. Annoyed, Ed answered with 'two needles' or 'half of Mississippi' but then said that he doesn't care. However, the Riddler thereupon whispered that it is Ed himself before vanishing. In this moment, the room door opened and Penguin came in laughing out of gladness and explained that he knew his old friend would understand his letter and come to Arkham. Due to Nygma's confusion Cobblepot responded that he was not talking to Ed but rather to 'him', the one who read his letter. Suddenly Ed saw the Riddler appearing next to Penguin, holding Oswald's torn and now stuck together letter in his hand and ordering Ed to read the first word of each sentence. Riddler then read out 'Please bring Ed to Arkham so I can set you free' before asking again 'What has two eyes but can't see what's happening in front of him' before shouting 'Ed Nygma' as the answer. Due to this reveal, Ed became tense and explained that he came here to save Lee and screamed that he is only Ed Nygma and that Lee believes in him and sees him for who he is. Consequently, Cobblepot yelled to Ed that he however sees 'him' and quickly ran to him to stop Nygma from leaving and pressed him against the desk. Penguin told his old friend that Lee Thompkins may have made Ed strong but he still sees the other one whose name he wouldn't speak. But because he has earned it and because he needs him, Oswald was now willing to say his name and thereon called him Riddler, causing the Riddler to finally break free and take control over Nygma's body. As soon as these words left Cobblepot's lips, the Riddler quickly calmed down, laid his pen down, adjusted his glasses and then looked straight into Oswald's eyes, asking him if they shall get to work before both of them bursted out into laughter, with Riddler now finally free from his inner prison once again.
Now reunited with his old friend, Penguin's top priority before escaping Arkham Asylum was to ensure Martin's safety and therefore sent the Riddler to free the boy from his captivity by the hands of Sofia Falcone. As The Riddler rescues Martin from Sofia Falcone's two thugs on Penguin's behalf, the latter approaches a guard at Arkham and is given a riddle, which he solves only to be punched in the nose. He lands in the infirmary where he is broken out by The Riddler as Bullock is distracted by Victor Zsasz and Headhunter, who have shown up to retrieve Penguin for Sofia. Penguin and The Riddler pay Lee a visit and Penguin tells her that he freed The Riddler in order to get himself out of Arkham. They tell her of their plan to take down Sofia, while involves Victor Fries encasing Penguin in a block of ice. Penguin is later cornered by Gordon and Bullock until a gunfight breaks out between them and Zsasz and Headhunter. The Riddler ends up being handed over to Sofia after Butch, who has since got his memory back, brings him to Tabitha and Barbara. He is tortured for information as Penguin, who was rescued by Lee, is encased in ice and delivered to her.
Shortly after Sofia and her henchmen left the Falcone Mansion, the Dentist still remained there in order to clean up his tools that were full of blood. Unnoticed by him, the ice block in which Penguin was locked up behind the Dentist started to crack due to a special heater developed by Mr. Freeze, whereon the complete ice prison ultimately scattered and the pieces slid over the whole floor, finally drawing the Dentist's attention who immediately turned around. However, Cobblepot then already held his former employee at gunpoint, screaming and asking the Dentist if he is working for Sofia too. Even though the Dentist yet tried to explain himself, Oswald just yelled at him that of course he is. The Penguin then asked him twice where Sofia is, while the Dentist still tried to explain how he ended up working for her, leading to Cobblepot to punch him in the face with the gun, causing his nose to bleed. Thereon, he revealed that Sofia left in order to find Arthur Penn before James Gordon does.
Oswald afterwards pulled out his flip phone and called his ally Lee Thompkins, who instantly asked him if the job is done already, but he told her that Sofia left the Falcone Mansion before he could kill her and is on her way to stop Gordon. He then ordered her to meet him at the Spa Bo'sh Sumka so they can kill her together before both ended the call. When Penguin turned back to the Dentist, he discovered the Riddler's bowler hat laying on a table. Right away, he turned his gun at the Dentist in order to further interrogate him, whereon he revealed that Sofia tried to get Nygma to turn on Oswald, that Ed endured a tremendous amount of pain and wouldn't give Cobblepot up. On Penguin's demand, the Dentist revealed that Falcone's thugs took the Riddler to the Gotham Docks to kill him. This now caused a strong inner conflict for Oswald, since it was very difficult for him to decide for either saving Ed or killing Sofia Falcone. However, he eventually chose to give up his revenge and left the Falcone Mansion to save Ed from Sofia's henchmen, while Lee Thompkins carried out the task of defeating Sofia in Cobblepot's place.
Two of Sofia's thugs had taken Nygma to the Gotham Docks, ironically to the same pier where Riddler tried to kill Penguin twice before and where he was once frozen in a block of ice by Mr. Freeze. The henchmen marched Ed to the end of the dock and then forced him to his knees in order to finish the task. One of them chuckled "Hey, I got a riddle for you. What's got a bullet in its head and sinks to the bottom of the river? You.", whereon both henchmen bursted out into evil laughter. Annoyed, Riddler said that the real torture is that those idiotic words will be the last he ever hears. As the thugs both held Nygma at gunpoint, he shouted at them to just kill him. However, two bullets then hit the clueless gangsters, killing them immediately. When both thugs fell on the ground next to him, Riddler instantly picked up one of their guns and turned around to point it at the one who shot Sofia's men. Edward then realized that it was Oswald who had just arrived in the Docklands and saved his life. Confused, he asked Cobblepot if he had already killed Sofia, but he said that he didn't kill her since she had left the Falcone Mansion to pursue Jim Gordon.
Riddler asked why he didn't just stay at Sofia's house and wait until she came there in order to kill her, whereon Oswald responded that then he wouldn't have been here at the pier on time. When Ed said "You gave up your revenge for me?", Cobblepot looked out to the Gotham River for a moment, he then walked a few steps closer to Nygma. Penguin said that trust is so very hard to find in Gotham City before revealing "but I trust you, Ed". They looked at each other for a while, then Oswald put away his gun, causing Riddler to do the same thing after a short moment of hesitation. Standing next to each other, both villains looked out to the Gotham River, remembering all the times they had been at this place. Edward then revealed that he has a strong desire to never, ever see this pier again. Penguin sighed "I agree", whereon he and Nygma turned around and left this cursed dock once and for all.
Alliance with Butch
Legion of Horribles
- "Mr. Oswald. Thank you for doing your part in hosting us today."
"Anything for an old friend."
- —Jerome Valeska and Oswald Cobblepot during the villain brunch[src]
After Sofia lost her power over Gotham's underworld and fell into a coma, Penguin took control of the now abandoned Falcone Mansion and moved into it. Once Jerome Valeska escaped Arkham Asylum, he started forming the Legion of Horribles, a terrorist organization consisting of the city's most dangerous villains, assembling Victor Fries and Bridgit Pike as well as fellow escaped Arkham inmates Jervis Tetch, Jonathan Crane and Oswald Cobblepot in one great league. Jerome then took the whole Legion to the Falcone Mansion, much to Penguin's dislike. Valeska had his followers from the asylum serve food and drinks to the guests, as he himself officially welcomed all of them to their first ever mandatory brunch meeting. He then gave an answer to the question everyone waited for, the reason for the gathering of this Legion of Horribles, as he calls the group. Noticing that this name has a nice ring to it, he orders one of his servants to write it down. Jerome begins explaining that he came up with a plan to turn the city into a madhouse back when he was in Arkham and that he is now at the cusp of making that happen, however he still needs help from all of them.
Thereupon, Mr. Freeze raised his arm, but Valeska commanded him to put all questions on ice until the end, before Jerome turned to Oswald, thanking him for doing his part in hosting them today. Cobblepot then responded that he would do anything for an old friend in a sarcastic tone, leading to Jerome asking Crane for the progress concerning Scarecrow's secret work. Next, Valeska calls Freeze an "ice man" and gives him the task of finding a big laboratory, since Victor is a man of science. He now turned back to the whole group and explained that all they need is Tetch to return with some very important information, but then started shouting at Carl, one of the servants from Arkham, ordering him to use the tongs to lay down the food. However, Firefly next accused him of still being silent about how he plans to take over the underworld, but Jerome stated that this is not his goal, instead he sees himself as an artist who just wants to paint the town crazy. Once that happens he could care less how the other members of the Legion of Horribles rip the city apart. Even though Bridgit seemed very euphoric for this proposal, Valeska explained that it is too early and nothing can happen until they have their one last essential ingredient, the one thing that will tie it all together. Right then, Jervis Tetch entered the Falcone Mansion and came into the dining room, leading to Jerome asking Jervis to sit down and join their conversation by pointing at the empty chair next to him, much to Penguin's curiosity.
Towards evening on this day, the members of the Legion of Horribles returned to the Falcone Mansion after fulfilling their individual tasks. Enraged that his brother Jeremiah Valeska was able to escape him, Jerome tried to calm himself again by tying his servant Carl to a chair in front of the fireplace and playing an altered version of Russian Roulette, trying to shoot Carl dead. Jerome eventually succeeded while Firefly sat on the couch and watched the whole event. Even though he killed Carl, Valeska stated that it didn't make him feel better at all. Right then, Penguin along with Solomon Grundy entered the Falcone Mansion, while Scarecrow went into the room and revealed that the test subject had arrived. Thinking Crane was talking about Grundy, Valeska commented on him as being too large for a test subject. However, Cobblepot explained Jerome that this is not his test subject and moved on by introducing Solomon Grundy to Valeska, stating that he will make a welcome addition to the team. Thereupon, Valeska inspected Grundy, commenting that he likes him since he seems scary. He then praised Oswald for recruiting a new member and greeted Grundy by punching him in the shoulder for fun, resulting in Jerome's hand to hurt due to Solomon's strong physiology.
Afterwards, Tetch and Mr. Freeze entered the room with a frightened civilian they hold hostage, Jervis explaining that they captured an unwilling businessman in order to test Valeska's plan. Jerome then grabbed the man by the collar and dragged him to Scarecrow. When the businessman begged them for not hurting him, Crane explained that this won't hurt a bit before spraying a strange violet gas into the man's face that first causes him to cough. However, shortly thereafter the man began to laugh softly, leading to louder laughter, while the man's face started to stretch to an unnatural extended smile and his skin turned pale white. Excited by the man's horrible transformation, Jerome started laughing along with him, stating that they are gonna need a lot more of this gas. Disgusted and shocked by this sight, most other members turned away from the two laughing men, except for Victor Fries, who apparently enjoyed it. The laughing toxin eventually showed it's full impact as the man's laughter turned into a piercing scream, leading to blood coming out of his eyes, killing him as a consequence.
Jerome Valeska's next plan was to abduct Interim Mayor Holden Pritchard, Commissioner Reynolds, Archbishop McGregor, Gertrude Haverstock, and Gloria Bainbridge. At night, the Legion of Horribles went to the Gotham City Hall where Mr. Freeze and Mad Hatter captured the mayor and the other members of Gotham's high society present. They took them to a van standing outside on the street, in which the other villains were waiting. Pritchard was still trying to convince Victor and Tetch to let them go, promising that he will double whatever they expect as ransom. Right then, the mayor saw Jerome Valeska standing in the van, who was scratched his nose unimpressed by these events and then smiled at the horrified mayor while Jervis handcuffed Holden to a metal rod. Upon noticing Valeska, Pritchard revealed that he has access to the police pension fund. Seemingly pensive, Jerome turned around and said "Wow, that could be a lot of money. Tempting, but, uh no, thanks.". Thereon, the mayor turned to Firefly who was standing next to Penguin a few steps away from Valeska. Pritchard said "Bridgit, isn't it? I can get you safe passage from the city, money, a new home...", but Firefly smiled and responded that it was people like him that locked her up in Indian Hill, and thanks to that, there is no Bridgit anymore. Pritchard immediately turned to Tetch and called him "son", promising that he can get him a pardon and that all will be forgiven, he just needs to stop this "lunatic". However, Hatter said that "lunatic" is a little harsh, he prefers "visionary".
The mayor then turned to Penguin, who was standing in the corner obviously not very happy about Jerome's plan. Pritchard asked Oswald if he can't do something, but Cobblepot put on a forced smile and said "Afraid not. I am with Mr. Valeska 100%.". As none of the villains were open for negotiations, Pritchard yelled that every cop in Gotham City will be looking for them, and when they find them, they should expect no mercy, just a hail of bullets. Jerome then started adjusting the mayor's tie and said "So serious. That's why your approval ratings are so low. Hey, tell you what. Try threatening me again, but this time, try it with a smile." When the mayor didn't start smiling, Valeska hugged Oswald with one arm and said "Aw, see, this is what's wrong. Nobody knows how to have fun anymore, right?", whereon Cobblepot nodded in agreement. However, Jerome then pointed at Scarecrow and said "But see our friend down there? Bag head? He's figured out a way to solve that.". Thereon, Crane came close to Gloria Bainbridge and used his laughing gas dispenser to spray the woman with the insanity toxin. While the gas showed his hideous effects by turning Bainbridge into a madly laughing clown, Jerome talked to the horrified members of Gotham's high society, telling them that it's time to give this city the boost it needs, time to stop taking ourselves so seriously. He then asked what Gotham has to lose, before looking at Gloria who was still laughing from the horrible gas, whereon he added "except your sanity". While Jerome bursted out into maniacal laughter to the delight of the other villains, Penguin seemed to be the only one who was disgusted by Jerome and his plan.
Jerome had Mr. Freeze and Scarecrow raid a chemical lab at Wayne Industries to make and obtain more laughing venom. Crane along with some of Jerome's followers then met with Mad Hatter and Penguin. They went to an airship hangar where Jerome wanted them to steal a blimp in order to disperse the laughing gas on the attendees of the music festival Jerome and Firefly were holding hostage in Gotham. Two blimp pilots noticed the unwelcome guests, whereon one asked them what they are doing in this restricted area. Crane responded that their cargo is too precious to waste while Penguin took a look at the giant airship. Scarecrow said "Let me give you something I like to keep up my sleeves for times just like these" before using his fear gas dispenser to spray a brown acid into the other pilot's face, causing him to scream in pain and collapse onto the floor to his colleague's horror. Tetch then asked the remaining pilot if he can steer this contraption alone. When he agreed, Mad Hatter proceeded to hypnotize the man. Jervis ordered him to look into his eyes while he used his ticking pocket watch to support the hypnosis, causing the pilot's face to become expressionless in the process. Finally losing his edge, Penguin told the other villains that the kidnappings, the concert in the Square was all to draw the biggest crowds, so they can drop the laughing gas on the people. Oswald then tried to put a stop to Jerome's plan by telling Hatter and Crane that this is madness. Scarecrow said that he thought Cobblepot would appreciate the beauty of it all, but that Jerome was right. Crane then revealed that Valeska anticipated Oswald's betrayal and that he knew Penguin would go to Jim Gordon. Mad Hatter then looked at Penguin in disgust about him betraying the Legion. While Cobblepot was still horrified by this reveal, Jonathan proceeded to command a thug called Judas to knock out Oswald. Hatter then ordered another follower to tie him up and put him on the blimp, since Jerome wants him to have a bird's-eye view.
At night on this day, Jim Gordon and Harvey Bullock stood in front of the now deceased Jerome Valeska as James received a call on his flip phone. It turned out to be Penguin, who greeted Jim in confusion and said that he is still on the airship over the Gotham River, whereon Oswald asked the GCPD captain if someone could please get him "the hell off of this thing". Gordon told Cobblepot that they are on it before he and Harvey crossed the street to get a better look at the blimp flying over the city. Jim asked Bullock how they are supposed to get a blimp down safely from over a river, but Harvey said that if Jim is asking him he would say they should let him stew up there for a few more hours. Gordon then talked to Oswald again and told him that they will get ahold of the standby pilot in order to have him advise. Jim told Penguin to sit tight and thanked him in the name of Gotham City before Gordon ended the call. Horrified, Oswald told Jim to wait, but then he noticed he had already ended the call. Enraged, Cobblepot threw his flip phone on the ground, thereon he began to freak out, furiously yelling "Jim!" multiple times into the night of Gotham City.
Betrayed by the Riddler
- "It won't make any difference. She's still using you. You are not the Riddler! You are a fool! God!"
- —Oswald Cobblepot yelling at the Riddler[src]
At night, tranquilizer darts hit all the police officers at Gotham Savings and Loan, causing them to pass out on the floor. Calmly, Lee and Riddler walked through the now unguarded bank, latter one saying that the pistol would have been more fun, whereon Thompkins told him that he indulges her. When Nygma told her that breaking open the vault is the last detail, Lee said that this is a big detail before asking him how he did solve it. Riddler then suddenly stopped walking and revealed that he had a little help from some friends. He passionately began to speak a riddle: "I'm the revealer of masks. When I appear, friend becomes foe. And the one that you love becomes the one that you hate. What am I?". Right then Penguin and Butch appeared behind Lee, latter one holding a crowbar, while Cobblepot answered the riddle by saying "betrayal". As Lee turned around in surprise, Oswald gleefully greeted her. When she looked back at Riddler, he aimed his gun right at her, revealing to her that it is not a dart gun before ordering the horrified woman to go ahead, whereon Penguin and Grundy followed them to the bank vault in order to break it open.
While Cobblepot and Grundy loaded all the treasures on the truck, Riddler held Lee at gunpoint and told her that this is the price for taking advantage of him, even though she insisted that this is wrong and that she wasn't using him. Since she called him "Ed", he informed her once again that he doesn't want to be called that, before he said that he is not wrong about her. Right then, Penguin returned to the vault room and reported that the truck is almost full meaning they should rather leave, whereon Nygma answered that Oswald should inform the ogre, referring to Butch, and that Gilzean should leave the property deeds, claiming they are all worthless since they belong to the Narrows. Cobblepot then began to laugh sadistically at Lee and looked over her shoulder, joking that this is how the tale of the Queen of the Narrows ends. He then gloated further by yelling "Goodbye, Lee" in her face before he bursted out into evil laughter and went into the vault where Butch was still picking up the treasures. Riddler watched as Penguin left them, afterwards he slowly put his pistol away and started to search around in his pockets, whereon Lee asked him what he is doing. Nygma spoke to himself, wondering how that did go again. He pulled a molotov cocktail out of his suit pocket and said "I'm the revealer of masks. When I appear friend becomes foe.". Lee said that the answer to that riddle is "betrayal", Riddler confirmed this, before lighting up the petrol bomb and throwing it into the vault on the Narrows documents lying around, lighting them on fire immediately, causing the alarm to go on. Horrified and surprised, Penguin and Gilzean turned around and tried to run out of the vault, but the bars already blocked the way out.
When Butch yelled at Riddler, asking him what the hell he is doing, he answered that he is just burning the Narrows property deeds, but Butch shouted that he wasn't referring to that. Enraged, Penguin yelled that Riddler is proving his love by betraying them. Butch threatened that these bars won't hold him and that he will be out very soon, but before he could end his threat Riddler interrupted him revealing that he and Lee will already be out by then. Nygma then turned to Oswald while coming closer to the bars and revealed to his old friend that he just wanted him to hear something, that they have been through thick and thin and that he holds no grudge against him but that Penguin comes against him if he comes against Lee. Behind Nygma, Lee smiled when she heard this, while Cobblepot's mouth was open widely in astonishment. Butch then tried to reach through the bars in order to grab Nygma, calling Riddler a "twerp" and threatening to dismember him. Riddler calmly told Gilzean that he won't even gonna try with him, before turning around and leaving the room, asking Lee to follow him while he passed by her. Enraged, Cobblepot yelled after Nygma that this won't make any difference and that Lee is still using him. While Butch bent the bars apart, Penguin shouted after Nygma that he is not the Riddler, but rather just a fool, before further cursing in anger. Shortly after, Lee allowed the GCPD to arrest her in order to distract them, giving Nygma enough time to escape the building. Butch eventually managed to tear the bars apart, whereon Penguin and Grundy also escaped into the night without getting caught, even though the bank robbery turned out to be a complete failure for these two villains.
A New Opportunity
The next day, Penguin watched an old black-and-white cartoon on TV at the Falcone Mansion. He sat down on an armchair and donned a napkin in order to use it as a bib. Thereon, he picked up a fried chicken leg from the small table in front of him, but right when he tried to to take a bite, Solomon Grundy who also sat in an armchair next to him tared the chicken leg out of Oswald's hands and ate it himself. Raging, Cobblepot asked him how long these petty agressions are going to continue, but Butch responded that there is nothing petty about his agressions. Sarcastically, Penguin asked Gilzean if he first has to starve until he can guess the source of Grundy's resentment. Frustrated, Grundy threw the chicken leg on his table and reproached Oswald since he said that if they joined forces they would be back on top, but instead they are grubbing for Jerome and got played by Nygma. And even though Penguin promised that he would find Butch a cure, he still remains a mutant. Cobblepot then said that he admits that through no fault of his own their advancement has not run a pace. Even more angry about this statement from Cobblepot, Butch yelled at him, making clear that they are just squatting in Falcone's Mansion, knocking over liquid stores to pay for groceries, while everyone else is carving up Sofia's territory.
Thereon, Oswald tried to justify these actions by telling Gilzean that they are lying in wait building a nest egg, while less deliberate players show them their cards. Very angry, Grundy pulled Penguin at the shoulder closer to him, threatening to crush his windpipe like a beer can if he won't find Hugo Strange and get him cured. Noticing a news report by Jennifer Luree on the TV, Penguin commanded Grundy to be silent, who actually felt incredibly furious that Oswald shushed him, leading to Cobblepot to shush him once more, explaining that he sees an opportunity here. Cheerfully, he realized that the Cult of Jerome invaded the GCPD in order to throw a wake for their deceased leader, whereon he got up and turned the TV off. However, Grundy questioned how that is an opportunity. Thereupon, Oswald explained that confusion is always an opportunity for the clear headed, that someone is showing his cards and added that they should go take a peek. The Penguin then left the room, whereon Grundy threw his napkin down on the plate full of chicken bones before getting up too.
An Unlikely Alliance
The next day, Barbara and Tabitha had a drink at the Sirens Club, both looking out of the nightclub's main window at gray smoke spreading from the position where the Gotham Clock Tower used to stand. Barbara revealed that she liked the Clock Tower and thinks it's destruction is a shame. She further explained that Jim took her there on a date once, but now they are both up in smoke. Tabitha said it is a good riddance and Barbara told her that Gordon always wanted to die a hero. However, Penguin then entered the Sirens Club out of nowhere, explaining that was Jim's problem. Thereon, the Sisters of the League immediately drew their blades. Butch Gilzean along with the captured and bleeding Jongleur entered the room behind Cobblepot. Oswald moved on and smiled while telling them that he would rather live well. Haughty, Barbara asked if that isn't little Penguin and Butch's corpse. Ashamed, Butch and Tabitha quickly greeted each other. Cobblepot revealed that Jeremiah Valeska is the man responsible for the recent fireworks, before turning to Tabitha, noting amused that he is the twin brother of Galavan's old associate Jerome. He then explained that Valeska has plans for Gotham and that he and Butch learned about them due to the "courtesy" of this gentleman, whereon Oswald patted Jongleur's shoulder. Obviously, Jongleur got heavily tortured by Cobblepot and Butch, therefore Jongleur told Barbara and Tabitha that they ripped out his fingernails.
Laughing, Penguin told them that he believes that this is a golden opportunity for cash and glory, revealing that normally he would keep both of them for himself. He then said that unfortunately he finds himself a bit short of the necessary manpower. Oswald then looked around in amusement and added "Or womanpower, if you will", before offering Barbara to go fifty-fifty on the take. She however rejects his plan, telling him that she will pass regarding an alliance with him. Penguin commented that her decision is pity, since he had hoped to finally be able to cure Butch of his condition with the money they were gonna make. Exactly as he had planned, this drew Tabitha's attention, whereon she asked him what he meant by that. The Penguin then explained that Hugo Strange ran Indian Hill and that it was Indian Hill's toxic sludge that turned Butch into a mutant, so it is only logical that Professor Strange can fix Butch. However, he then noted that it won't be cheap. Butch looked at Tabitha and told her that Strange might be his only hope. Demanding, Galavan turned to Barbara and looked into her eyes, but she ordered her to stop looking at her like that. Upset, Tabitha told her that she almost got killed fighting Barbara's ex-boyfriend's rotting corpse and shee thinks it is time to return the favor. Reluctantly, Barbara agreed, but she insists that Swamp Boy keeps his funk ten feet from her at all times. She now turned to Oswald, asking him what he had in mind, whereon a mischievous smile appeared on his face.
Jeremiah then sat down on a chair next to the bound and gagged Jongleur in order to negotiate with Penguin and his allies. When Valeska heard they demand $50 million, Valeska sceptically asked "$50 million. That's what you want?", whereon Cobblepot told him that it is a nice round number, but Jeremiah explained that he doesn't quite has that on him right now. However, Oswald then said that Jeremiah gave mayor Pritchard six hours to evacuate Gotham City, an impossible task, whereon Cobblepot advised Valeska to let the mayor buy another hours. Thousands of lives will be saved that way, so $50 million will seem cheap. Jeremiah said "I see. I play the villain, you get away scot-free and rich.", causing Oswald to nod in agreement. When Valeska said that he will get them the money and they give him back his core relay, Barbara patronized him saying "That is usually how a handoff works". Oswald slightly smiled when he heard her statement and then listened when Jeremiah said that they drive a hard bargain but that he will see what he can do. Barbara was surprised that he gave in to their demands just like that and stated that after knowing his brother she expected something more..., whereon Jeremiah finished her sentence with the word "insane" and claimed that he is nothing if not sane and reasonable, two things his brother never valued. Thereon, Jeremiah said that this is why he will be successful where Jerome failed, before adding that he is also vastly more intelligent than his brother.
After he got his flip phone out of his coat pocket, Jeremiah smiled at his opponents and said that he will now see about their money, before he got up and started to walk around during the call. He introduced himself to the person on the other end and announced that he has additional demands. Even though Valeska's interlocutor didn't seem too happy about that, Jeremiah said that he wants $50 million, unmarked bills and that he will tell them the location. As Jeremiah diappeared in the background of his safehouse, Tabitha quietly asked Penguin if they really want to hand the core relay over and let Jeremiah destroy Gotham. Annoyed by her question, Oswald began to roll his eyes and loudly announced that this is not, of course, his plan, but announced that once they get the money they kill Jeremiah and his people, give the core relay to the police, split the $50 million, and are hailed as the heroes of Gotham. As Cobblepot smirked after explaining his clever plan, Tabitha added "And we cure Butch", whereon Penguin said "And that. Certainly.". While standing behind some wooden crates near the other side of the warehouse, Jeremiah just ended his call and said "Would you believe it? They put me on hold." As Valeska told his opponents that there is always plan number two, he picked up a bazooka hidden behind the crates.
Barbara yelled at their allies to get down while Oswald asked Jeremiah to wait, then they all hid behind the walls as Valeska blew up the bond and horrified looking Jongleur who stood in the middle of the room, whereon smithereens hit all the villains present. When the smoke settled down, Jeremiah drilled in his ears while Barbara and her allies emerged from the walls they hid behind, still coughing from all the smoke. Penguin yelled at Jeremiah, asking him if he is out of his mind, but Valeska simply asked him why people keep insisting he is insane, since he thinks there is nothing insane about having a backup plan, something Jongleur never knew about. After he removed some dirt from his coat, Valeska told his horrified opponents that just so they know this building is within the blast radius and because of their interference, he plans on detonating the bombs as soon as he is far enough away to observe the destruction in peace. When Barbara shouted that he promised the city six hours, Valeska calmly asked her whose fault it is that he changed his mind. He then ordered his followers to tell their men to rewire the bombs to work in direct sequence before commanding the rest of them to kill "these idiots". As Jeremiah ran up the stairs to escape the building, the cultists began to shoot at Barbara, Butch, Tabitha and the Sisters of the League, who returned the fire while Oswald hid behind a wall in fear.
While Barbara, Butch and Tigress fought Jeremiah's followers in a massive shootout, Oswald hid behind a broken wall in fear. Angry, Barbara shot the armed thugs while she said "Get the core relay, he says. Have the upper hand, he says." to Cobblepot. As one of Jeremiah's last remaining soldiers ran towards them, Butch knocked him out by hitting him with his gun and then threw the follower into a wall right next to Penguin. After Tigress had shot the last cultist, she said "finally", whereon Oswald quietly emerged behind the wall he was hiding at, while Tabitha told her allies that they should get the hell out of here before Jeremiah blows them all to smithereens. Enraged, Butch grabbed Cobblepot by the collar and told him that this is all his fault, but Penguin finished the sentence for him, revealing that he knows he needs to fix it. Thereon, Oswald began to search around his suit pocket and got his flip phone out. He called Harvey Bullock at the GCPD who answered the call impolite as always. As Penguin just said "Harvey", Bullock asked if this is Oswald, whereon he gave Lucius Fox a hand gesture that suggested he should overhear their conversation. Even though Bullock claimed that he is kind of busy at the moment, Cobblepot revealed that he has information regarding Jeremiah Valeska's plan, but Harvey simply asked him what information he has.
As one of Jeremiah's followers lying on the ground was still moving and groaning, Tabitha immediately shot him dead right next to Penguin's ear, who covered his ear in annoyance. Having noticed the shot, Bullock asked if he just heard gunfire, but Oswald ordered him to just listen, whereon he revealed that Valeska is not honoring the six hours, that he will blow the bombs as soon as he can watch the catastrophe from a safe distance. Oswald then told Harvey that Jeremiah said something about rewiring the bombs to communicate with each other, he called it a direct sequence. As soon as he heard this, Lucius stopped listening to Penguin's call and immediately started to search around the maps and technical plans lying on the desk. Since Lucius repeated "communicate with each other", Bullock noticed that Fox knows what Cobblepot is talking about and simply ended the call, whereon Penguin yelled "Harvey!" full of anger before throwing the flip phone onto the ground. At the GCPD, Lucius explained Harvey that it is a backup system from when they operated as batteries, meaning that they can be disrupted by disarming the first bomb in the sequence, like removing one light from a string of Christmas lights. However, Harvey pointed out that they have no idea where the bombs were.
At night, Penguin, Barbara, Butch and Tabitha returned to the Sirens Club. Barbara took a whiskey bottle and put it down in front of Tabitha and Butch who were sitting at the bar. Galavan told Barbara that she would have been way off if she would have been asked this morning how many people she was gonna kill today. Behind her, Penguin ran back and forth nervously and said that perhaps the outcome was not what they had hoped but that it was worth the risk regardless. Furious, Barbara poured whiskey into her glass while advising "Ozzy" to "limp out of here" while he still can. Cobblepot said he is fine with that, whereon he turned around to leave the nightclub and told Butch that they are going. However, Gilzean simply refused and got up from the barstool, whereon Penguin immediately turned back in surprise. Butch said that everything went wrong ever since they teamed up and that they don't even know where Hugo Strange is. However, Oswald then walked towards him and revealed that he actually does know where Strange is, causing Butch to freak out and yell at the frightened Penguin. While Gilzean choked Cobblepot with his bare hands, Penguin claimed that he just got word, but Butch shouted into his face that he doesn't want to hear any more excuses and that Strange will fix him right now. Still choked by Grundy, Oswald asked how they are supposed to pay Hugo Strange, whereon Tabitha came close to Penguin's face and whispered that she can be very persuasive.
Later the same night, Tabitha, Butch and Cobblepot tracked down Hugo Strange and took him to the Falcone Mansion where they ordered him to search for a cure that can turn Gilzean back into an ordinary human.
Battle for Gotham
- "One question. Who do I get to kill?"
- —Oswald Cobblepot to the Sirens, Alfred Pennyworth and the Sisters of the League.[src]
At the Sirens Club, the Sisters of the League were preparing for the inevitable battle while Tabitha informed Barbara that Jeremiah had already escaped from the GCPD building by the time she got there. Thereupon, Alfred Pennyworth entered the nightclub and confirmed Tabitha's statement before asking where Ra's al Ghul is. Barbara then guessed that Ra's helped Jeremiah kidnap Bruce, so Alfred came to the Sirens Club to find Ra's. Alfred asked her a second time to tell him where Ra's is, but Barbara revealed that she doesn't know where he is, but where he is gonna be. She explained that Ra's is planning to leave Gotham tonight, after turning the city to a pile of rubble. Barbara then assumed that Jeremiah Valeska will help Ra's before suggesting a deal to Alfred and Tabitha. She proposed that Galavan gets to kill Jeremiah, Alfred gets to rescue Bruce and Barbara herself gets to kill Ra's. In disbelief, Pennyworth asked her how she plans on doing that, whereon Barbara revealed that she has got a little surprise for him, while she patted a small case containing the reassembled cursed dagger of Ra's al Ghul. Right then, Penguin entered the room, carrying a machine gun and telling them that he has one question for them.
While Pennyworth pulled his gun and the Sisters of the League drew their blades, Oswald continued talking and wondered whom he gets to kill, revealing that he wants to join the battle on the side of the Sirens organization. Mischievously smiling, Cobblepot explained that the only way to keep Butch on Hugo Strange's operating table was that Oswald promised him that he would take Gilzean's place and come to help the Sirens. Barbara then took the case with the cursed knife while noting that now they make quite the little gang. She then asked her allies to follow her by saying "Let's do this", whereon the Penguin, Alfred, Tabitha and the Sisters of the League left the Sirens Nightclub along with her. A powerful resistance alliance against the Valeska/Ra's al Ghul collaboration had formed, ready to defend Gotham City and engage the League of Shadows.
Shortly after, Barbara Kean along with the cursed knife arrived at the building where Ra's al Ghul, Jeremiah Valeska, Bruce Wayne and the League of Shadows were preparing to watch Gotham City's destruction. At first they think Barbara came alone, however, Penguin then started screaming and shooting a machine gun at the League, while the whole alliance of Tabitha Galavan, Alfred Pennyworth and the Sisters of the League appeared behind him and began battling Ra's al Ghul's men. During the battle, Ra's managed to defend himself against Alfred and the knife wielding Barbara and then asked her if she will never learn, but she finished the sentence for him, telling him she gets that the knife has to be held by Bruce Wayne only, before attacking him once again. At the same time, Jeremiah takes Bruce hostage and shoots a member of the Sisters of the League, as Tabitha's whip ties his hands together, allowing Bruce to free himself. Galavan then laced her whip around Jeremiah's throat, trapping him in stranglehold and forcing him to his knees in front of her. She told him that this is for Selina, but before she could harm him somehow, Valeska managed to draw Tabitha's own knife and stabbed her leg. Surprising her with this attack, Valeska then grabbed Galavan, threw her on the ground and tried to crush her throat with one hand. While lying on her, he came closer and closer to her eye with the knife he held in his other hand, smiling sadistically while telling her that it must be very disappointing for her to die like this in case she wanted to avenge Selina.
Right then, Valeska got shot in his shoulder by the Penguin, who participated in the fight near them. Surprised that out of all the people it was Cobblepot who saved her life, Tabitha looked at him in confusion, not knowing yet that he only kept her alive for his completely different intentions that he still plans to implement in the same night. After knocking out Palden, Bruce now tried to fight Ra's, but he as well as Barbara and Alfred got defeated instantly. While Ra's al Ghul was busy with fighting Alfred, Barbara forced Bruce to hold the cursed blade along with her, before ramming it into Ra's stomach. This event even caught Valeska's attention, who was still lying on the ground from his gun wounds and now looked at them in astonishment. While cracks out of fire and ashes arising from the wound started to tear Ra's body apart, he looked at Barbara Kean, saying "Well done, Barbara". Right then, the sound of an explosion shook the whole city, drawing the attention of Barbara, Bruce and Ra's, as well as the horrified Oswald Cobblepot and Jeremiah Valeska, latter one smiling savagely as one of Gotham's main bridges collapsed into the Gotham River in a force of fire.
But this should not be the last one, since multiple other bridges followed the same fate, crashing into the water after their connections to the mainland gave in to fire and explosions. Shocked by this sight, Penguin, Barbara, Tabitha and Alfred witnessed power failures affecting the fallen city. Right then, Ra's drew Bruce Wayne's attention by grabbing him by his shoulders and sinking to his knees at the same time. Ra's looked into his eyes and told him that the choice is now his, that he can either stay Bruce Wayne or accept his destiny and become Gotham's dark knight. While Ra's al Ghul's body turned into ashes and fire and his voice became disfigured, he bend back one last time before a storm of lava hit him, incinerating him and leaving only the cursed dagger behind that fell onto the ground. Horrified, Bruce then turned his head towards the burning city. By this point, Jeremiah Valeska had already taken advantage of the general chaos and confusion. He had managed to escape the building into the night of the abandoned city, remaining on the loose. The battle for Gotham was over and the alliance against Valeska and Ra's had failed to prevent the city's downfall.
Revenge on Tabitha
- "Did you think I forgot that you murdered my mother? That I just got over it? I have lived with that pain every day. I could have killed you any time I wanted, but I believe in an eye for an eye. You took away the one person I love, so I took away the one person you love. And you get to live with that. [...] But don't worry, in time, when I feel that you have suffered enough I will kill you, too!"
- —Oswald Cobblepot to Tabitha Galavan[src]
Shortly after, Penguin and Tabitha return to the Falcone Mansion, where Galavan immediately holds a blade to Hugo Strange's throat and asks him where Butch is and what he did with him. However, Gilzean then stepped out of the shadows behind her, with his human form now completely restored. Touched by the cure, both lovers reunite by confessing their love for each other and sharing a passionate kiss. Butch then turned to Cobblepot, who was watching them in glee the whole time. He told Penguin that he will never forget this and that he is there for him no matter what he needs. Oswald thanks him and tells Butch that he considers him a friend. However, he confesses that he is truly sorry to the confusion of Tabitha and Butch, right before pulling his gun and shooting Butch in the chest. Butch collapsed on the floor, instantly dying in Tabitha's arms. From the other end of the room, Penguin softly asked the shocked woman if she really thought he forgot that she murdered his mother, that he just got over it. Oswald then reveals that he had lived with that pain every day for the past few years.
Moreover, he explains that he could have killed her anytime he wanted, but that he believes in an eye for an eye. She took away the one person he loved, so he took away the one person she loved, something she should get used to live with. Enraged, Galavan ran to Cobblepot in order to kill him, but he casually used his gun a second time and shot her right in the leg, causing her to kneel down in front of him from the pain. Still in disbelief and shock, she asks him if all of this finding Strange, curing Butch, was all so he could kill him in front of her. Penguin confirms this and then looks right into her eyes, telling her that she shouldn't worry, since he plans on killing her too, but only in time when he feels that she has suffered enough. Full of hate, she tells him that this won't happen if she kills him first. Gloating, Cobblepot says that she is welcome to try, before having her carried out of the Falcone Mansion by two of his henchmen, while Tabitha is still groaning and threatening to kill Penguin. Oswald then looked at Butch Gilzean's motionless body, somewhat feeling sorry that he had to kill his old friend in order to get his revenge.
Later that fateful night, Penguin's henchmen found the dead bodies of Edward Nygma and Lee Thompkins in the Narrows. Shortly after, Cobblepot ordered them to take the bodies to the Falcone Mansion. Before Oswald left the Manor with two of his allies, he ordered one of his men to inform Hugo Strange that he wants him to revive Lee and Ed.
No Man's Land
Return to Power
- "Yes...this will do nicely..."
- —Oswald Cobblepot when taking over Gotham City Hall[src]
No Man's Land: Day 87
Oswald gets fitted for a leg brace that allows him to walk without his cane. He requests that a knife be placed on the brace. As Oswald sits down to enjoy his dinner, Penn comes to report an accident that caused another shutdown at the factory where a worker passed out from hunger and fell into a hydraulic press. Oswald says he feels for their workers, but he can not give them food that he doesn’t have. He takes a bite of his steak and yells that it is overcooked. His dog, Edwards whines and pants, so Oswald gives his dinner to him. Penn tells Oswald they’ve had more misfires with their guns. Oswald denies this and shoots his gun into the air to prove it, but when he goes to fire again, it misfires, hurting his hand and proving Penn’s point. Suddenly, Oswald thinks he hears a chopper and tells Penn to be quiet, so he can hear it better.
To be added...
Confrontation with Scarface
In order to construct the submarine that they planned to leave Gotham in, Oswald and Nygma later met at the Gotham City Public Library. The Riddler was angered that Cobblepot was trying to take control of the project even though he didn't even help building the submarine. However, they are then approached by Arthur Penn, who had turned into the Ventriloquist after secretly surviving the attack at Haven. Controlled by Scarface, Penn reveals that him and the dummy plan to take over the Penguin's criminal empire and territory, as well as his hidden treasure. When Penn and Scarface learn about the plans to build a submarine, they decide to kill Cobblepot while letting Nygma live in order to complete construction. Before Penn can shoot Oswald, latter one is able to blow Scarface's head of with the help of Nygma, freeing Arthur of the wooden dummy's influence. Even though Penn was back to normal, the Riddler then proceeded to shoot the former accountant dead, noting that he was a lunatic that had to be stopped once and for all.
To be added...
No Man's Land: Day 391
Preparing for the fight to save Gotham from Nyssa al Ghul's madness, Penguin is given a gun, knife, as well as sunglasses by his minions; if he's going out, he's going out in style. At the perimeter wall surrounding Gotham, he teams up with Gordon, Bullock, the GCPD, and Riddler to fight off Bane's army, where his right eye is brutally injured.
Locked Up In Blackgate Penitentiary
After the events of No Man's Land, Oswald Cobblepot and Edward Nygma swore a pact with each other to take what they want when they want and suffer no fault. However, six months later, Nygma is incarcerated to Arkham Asylum and Cobblepot is incarcerated in Blackgate Penitentiary by Jim Gordon.
10 Years Later
Revenge On Jim Gordon
Following his imprisonment, Cobblepot, despite the fall of his criminal empire, continued to retain his strong reputation within the criminal underworld and overtime, his long imprisonment caused him to gain amount of weight, alongside gaining a glass replica of his mutilated eye, which he disguised with a monocle. Eventually, Cobblepot's sentence comes to an abrupt finish as he exits Blackgate to the company of those who were still loyal to him before declaring to the press, who were pestering him over his intentions against Gordon, "The best revenge against Jim Gordon is serving the city I love." Afterwards, Cobblepot noticed that several spies were placed around the area by the GCPD and called out one of the journalists on his deception in the process. Following this, Cobblepot tracked down Gordon following his first encounter with the unknown vigilante attacking the mobs, and held Jim at gunpoint whilst he forced him to drive to the pier, reminding him of his decision to spare his life before taunting him over his regret for not doing the deed. However, Cobblepot's necessity for the emotional release of his revenge was shattered when Gordon, who was careless about his revenge, accused him of placing the bomb inside Wayne Tower, though while Cobblepot claimed to have not known what he was referring to, this distracted him long enough to allow him to dive into the water and escape, much to Cobblepot's horror and frustration.
Meeting the Dark Knight
Soon after, Cobblepot rescued Nygma from police custody at Wayne Tower, with the two of them renewing their friendship and catching up on the last decade that they have spent apart from one another. Unfortunately, this joyful reunion was short lived as the vigilante landed on the roof of the limousine and knocked out the driver, causing him to crash into a lamp post. Following this, after Cobblepot and Nygma make a hasty escape from the destroyed limousine, they both see the vigilante for the first time and scream in absolute terror; after being tied together and hung from the top of the lamp post, Cobblepot and Nygma are threatened by the vigilante, who declares, "Gotham is mine," before leaving them to be found by the police, placing them in an embarassing situation. Afterwards, the two of them are arrested and placed inside a prison transport van for Blackgate, though Nygma picks the locks on their handcuffs and the two of them leap out of the van's backdoors, deciding to work together to get revenge on the vigilante, though after seeing him leap across the rooftops in the sky, they nervously decide to wait until tomorrow before planning their revenge and made a quick escape down the street.
- "Your son... is a coldblooded psychopath. I can't count how many men he's killed. My own friend, Frankie Carbone, he stabbed him a dozen times. What kind of person plunges a knife into someone over and over? You know, don't you? I can see it. Did you catch him one night washing the blood from his hands? When did you realize that you had given birth to a monster?"
- —Sal Maroni to Gertrud Kapelput[src]
At first glance, Cobblepot appears to be milquetoast, subservient and somewhat of a sycophant. In reality he is a man ambitious and cunning who is willing to do whatever it takes to obtain power. Despite this hunger, Cobblepot is patient and uses his high intellect to concoct plans in order to reach his goals. Virtually every move he makes is premeditated to a certain degree. While vengeful he has demonstrated a ability to work with enemies when a bigger threat presents itself, though will patiently plan their downfall with merciless cunning and cold precision should the opportunity present itself. A prime example is his working relationship with Tabitha Galavan. When Tabitha murdered his mother Cobblepot reluctantly worked with her on several occasions despite the two of them hating each other. When Tabitha looked to cure Butch Gilzean, Cobblepot had Hugo Strange cure him under the pretense that their rivalry was quashed only to kill Butch in front of Tabitha. He explained that it was an eye for an eye as Tabitha would now have to live with the fact that the man she loved had died as retaliation for his mother’s murder. However, he had no qualms in killing Tabitha when she confronted him only a few days later.
Even when things don't go exactly as planned, Cobblepot is highly adept at playing the hand he is dealt for the best. He is more than willing to kill someone when he feels it's necessary. He speaks often with a smile, talking fast and shaky, with variant levels of flattery to whom he speaks to, often sarcastically.
Despite his malice and ruthlessness, he has a softer side and a degree of humanity when it comes to his mother whom he loves deeply and devotedly and his father whom he also loved but knew for a little amount of time. When his mother got killed, it devastated him deeply and when Edward said that his mother was his weakness, Oswald almost slit Edward's throat, saying his mother was the only person who truly cares and loves him. His father's murder shocked him out of his mental conditioning by Hugo Strange and prompted him to kill his stepfamily for killing Elijah. He also started to care about Edward Nygma and became a close friend. When Edward was unconscious after Butch nearly strangled him to death, Oswald was scared and worried about Edward being dead, but was relieved when he woke up. He even took care of him when Edward had a sore and bruised throat after the strangling. When Edward didn't come home for 12 hours, Oswald tried to file a missing person report when he thought Edward was kidnapped and hugged Ed when he came home. Oswald even comforts Edward after Isabella's death and helps him move on. He also displayed a rare moment of gratitude and respect for his former boss and rival Fish Mooney. When Mooney told Cobblepot that she could not kill him as she felt her proudest achievement was turning Oswald Cobblepot into the crime boss the Penguin , he seemed to develop a newly found respect for her and allowed her to leave unharmed. He was also visibly distraught when Gordon killed her under the influence of the Tech Virus .
At first, the name "Penguin" infuriated him, to the point of murderous intents, but he later decided to accept and adopt the epithet, admitting that it "grew on him." With the current outfit, name and mannerism, he is gradually becoming closer to his original concept in the comic books.
The rapidity and precision of his Biblical references when he was picked up outside Gotham by the church group suggest that Christianity played a role in his upbringing. His facial expressions declare that, like the spoiled only child he seems to be, Oswald was frequently a target of bullying in his youth. As seen with a young orphan named Martin, Penguin would never use an innocent child as a pawn in his plans. He put in the effort to fake Martin's death and help him disappear, displaying Cobblepot's humanity. He was even reluctantly willing to eat human flesh just to save an orphan's life.
- "The man with the knife was short, fancy clothes, walked funny."
Oswald Cobblepot is a skinny young man of about average height, with pale skin and noticeably bright blue eyes. His nose is slightly pointed and beak-like. His black hair styled and messily plastered on his head, with some spiky ends pointing erratically at the top of his head. His attire consists of expensive custom made suits of many variations with an assortment of different neckwear as well and is mostly carrying a black umbrella. Due to the beating he suffered for betraying Fish Mooney, one of his legs was permanently damaged having never healed properly, forcing him to walk with a noticeable limp with many comparing it to a "penguin". Later on, he started utilizing a Penguin themed cane to aid him while walking. Currently, his hair is styled upwards, no longer having plastered parts on his head.
In his later life, Cobblepot gained weight and had a permanent damaged eye following a shootout with Eduardo Dorrance's forces during Gotham being a No Man's Land. He wore a purple jacket, and began wearing a top hat and a monocle over his blinded eye as part of his new attire after leaving prison.
- "A year ago, I held Fish Mooney's umbrella. Now she's dead by my hand. Along with Maroni. Falcone is in hiding and all of their businesses are mine. They all underestimated me. I suggest you not make the same mistake."
- —Penguin to Theo Galavan[src]
- High-level intellect/Master Tactician/Leader: Oswald is methodical in creating plans that are meant to benefit him, and is often called "perceptive" or "clever." He managed to orchestrate a gang war between Maroni and Falcone that he hoped would result in their deaths and allow him to control Gotham's criminal underground. He is also capable of running a criminal organization without getting caught by the GCPD. He was also able to convince the citizens of Gotham that Fish Mooney and her gang of "monsters" were a serious threat to the city, despite his status as a criminal.
- Master of deception: Oswald is able to manipulate others and use them in his plans. He managed to convince Irish hitmen to kill Maroni by telling one of them it would make them Falcone's top hitmen instead of Zsasz, when in reality he planned to have them killed by Maroni and his men. While working as a double agent in Maroni's organization for Falcone, he was able to prove his usefulness to Maroni, with the latter not realizing it was all a ruse.
- Patience: Oswald is an extremely patient man. He managed to wait 2 years before setting up his plan to get revenge on Tabitha, in turn killing Butch, and days later killing Tabitha
- Indomitable will: Oswald has showed no reaction after being stabbed in the hand with a pin by Fish Mooney. He was also able to kill Mooney and escape from the GCPD, despite being shot both times. He has shown to almost never give up on getting revenge towards those who have wronged him. He also was willing to let himself be killed to protect Nygma due to his love for him.
- Intimidation: While most people do not take him to be a serious threat, he is able to intimidate several people with threats of violence, such as Liza.
- Network: As a crime lord, Oswald has connections to multiple crime families and hitmen.
- Singing: Oswald is skilled at singing as shown when he performed in duet with Nygma in the latter's apartment.
- "I'm sorry! I don't think he can hear you through the bullet in his ear!"
- —Oswald Cobblepot to Bane[src]
- Expert marksman: Oswald is capable in the use of firearms. This is seen when he shot the rope holding up a guillotine.
- Skilled knife-wielder: Oswald is capable to use knives. He quickly stole a fisherman's switchblade and slit his throat, and later improvised a broken beer bottle to stab a passenger in the neck.
- Combatant: Oswald has shown some skill in brawling, this seen when he fought against Fish Mooney.
- Piano Oswald has been depicted able to play the piano at Fish's Mooney's club.
- Torturer: Oswald is able to inflict brutal torture on several of his victims without restraint, such as when he beat Theo Galavan with a bat multiple times.
- Toxicology: Oswald has some knowledge of poisons as he laced the cannolis he served to the bank robbers he hired with a unknown poison that killed them.
- Penguin cane: Cobblepot carries a cane with a penguin head on it that is pulled out to become a knife/sword-like blade.
- Umbrellas: Cobblepot often carries an umbrella with him as his best-known identification sign. Before he got a proper cane, he not only used umbrellas to protect him from rain, but also as a walking aid.
- Top Hat: Cobblepot was shown to wear a top hat, mainly in the episode "The Beginning...", after being released from Blackgate.
- Monocle: After having his right eye injured by Bane and his army, Cobblepot wore a monocle, after being released from Blackgate.
- Cigarette Holder: When he was released from Blackgate, the Penguin kept a slender cigarette holder in his suit pocket, implying that he probably started to smoke at some point during his ten year prison sentence.
- Guns/Firearms: Cobblepot has used a variety of firearms such as pistols, shotguns, assault rifles, and machine guns.
- Knives: Cobblepot has used a knife (or an improvised variant) multiple times.
- While most versions of The Penguin tend to accept and like the nickname "Penguin", this version has a great dislike for the nickname, even going so far as to kill someone, if he can get away with it. However, with some advice from Sal Maroni, he begins to embrace the nickname. In season 2, he begins to address himself with the name and is comfortable with it and by season 3 insists people address him by the name.
- Cobblepot is revealed to be 31 years old, which makes him 17 years older than Bruce Wayne. Since Bruce normally starts off as Batman at the age of 25, by then Cobblepot will be 42.
- Cobblepot is thin in the Gotham series, while he is obese in the comics and a majority of his other incarnations.
- This incarnation of the Penguin has been very well received with critics and viewers alike, with Robin Lord Taylor's portrayal also praised. Actor Danny DeVito (who portrayed the Penguin in the Tim Burton film Batman Returns) praised Taylor's performance. Taylor himself had previously stated he used DeVito's Penguin as inspiration for his version of the character. Actor Mark Hamill, best known for voice acting the Joker in the Animated Series and Arkham Games also praised him.
- This is the first version of the character Penguin to be shown romantically attracted to a male character, the character was a close friend Edward Nygma.
- Penguin has cheated death more than anyone in the series.
- Like Ra's al Ghul, Penguin foresaw a great conflict coming to Gotham and warned Jim Gordon of its inevitable arrival.
- In DC comics, Oswald Cobblepot was created by artist Bob Kane and writer Bill Finger and he was introduced in Detective Comics #58 (December 1941). According to Kane the character was inspired from the then advertising mascot of Kool cigarettes – a penguin with a top hat and cane. Finger thought the image of high-society gentlemen in tuxedos was reminiscent of emperor penguins.
- While Bruce Wayne has come into contact with Penguin numerous times during Season 2, it wasn't until Mad City: Anything for You when Penguin interacts with Bruce for the first time directly.
- Gotham marks the third live-action appearance of the Penguin (and the second in television), with the first being in 1960s television show Batman in which he was portrayed by Burgess Meredith and the second being Danny DeVito in Batman Returns.
- Both of Oswald's parents were murdered.