- "You shall become the Demon's Head. The League of Shadows will be yours to command. An army of assassins."
- —Ra's al Ghul to Barbara Kean
The League of Shadows is an ancient and powerful secret organization of highly trained assassins led by Ra's al Ghul. Known members are Ra's al Ghul and Sensei. After Ra's' death, his title was later passed to Barbara Kean, thus dubbing her as their new leader until Ra’s was resurrected and deemed Barbara unworthy, retaking command of the league, but the Sisters of the League defected and continued to follow Barbara as members of the Sirens.
After Gotham became a No-Man's Land and Ra's Al Ghul was killed once again by Barbara and Bruce Wayne, the male members of the League of Shadows agreed to pledge themselves to Barbara's leadership. However, she instead had the former Sisters of the League kill them, blaming the corruption of Gotham on men always holding power. This led to the end of the League's known influence in Gotham. However, according to Nyssa al Ghul, the League is still alive all around the world.
The League of Shadows is revealed to have manipulated the Court of Owls into doing their bidding. Some of its ninjas attacked Fish Mooney, Oswald Cobblepot, Hugo Strange, Victor Fries, and Bridgit Pike at a slaughterhouse where Hugo Strange's earlier cures for Alice Tetch's poisonous blood was being held. Most of the assassins there were killed by James Gordon which also ended with Fish Mooney accidentally getting killed. Other assassins from the League of Shadows were present at the Yuyan Building when Bruce Wayne first meets Ra's al Ghul.
After killing Niles Winthrop which led to Alex Winthrop going on the run, Ra's al Ghul meets with Barbara Kean as he sends Anubis and The Hunter to track Alex down. While Bruce and Jim Gordon defeat the two operatives, Ra's al Ghul shows up and holds Alex at knifepoint in order to get the embalming knife from them. When Bruce was reluctant to give up the embalming knife, Ra's al Ghul slit Alex's throat and then surrendered to Gordon.
To further his plans, Ra's al Ghul secretly had some members of the League of Shadows infiltrate Blackgate Penitentiary and replace some of the guards. When Barbara Kean visits him with a plan to break him out, Ra's al Ghul declines her offer and transferred some of his energy to Barbara for her to use at a later date. When Bruce Wayne infiltrates Blackgate Penitentiary to deal with Ra's al Ghul, he is subdued by the disguised League of Shadows members and taken to Blackgate Penitentiary's sub-basement. While the fake prison guards deal with Jim Gordon and Alfred Pennyworth, Ra's al Ghul tempts Bruce into using the embalming knife on him to end his curse. Jim Gordon and Alfred Pennyworth defeat the guards and arrive in the sub-basement to find that Bruce had given in to Ra's al Ghul's temptation and had used the embalming knife on him. When Blackgate Penitentiary goes into lockdown after what happened inside, Alfred talks to the police while Gordon tells Bruce that they will cover up what happened by telling the public that the League of Shadows infiltrated Blackgate Penitentiary and made off with Ra's al Ghul.
After understanding that the energy that Ra's al Ghul placed in her is a beacon to summon the rest of the League of Shadows to Gotham City, Barbara is confronted by it's members. One League of Shadows captain doubts that a woman can hold the title of "Ra's al Ghul" and tries to take it from her only for Barbara to kill him. When Barbara asks if they would still be loyal to her, most of it's members bow to her. Just then, the lights go off and automatic gunfire is heard. When the lights come back on, the female members of the League of Shadows are revealed to have killed off the weaker ones as they pledge their loyalty to her.
Lelia and the Sisters of the League take Barbara and Tabitha Galavan to Ra's al Ghul's Vault where only Barbara uses the power of the Deamon's Head to open the vault. She sees a portrait of what looks like Ra's al Ghul and Barbara Kean causing her to accept her destiny. When Tabitha later comments about this and asks how this will affect their business, Barbara ends her partnership with Tabitha and has Leila and the Sisters of the League remove her. Outside, they beat up Tabitha as Leila states that they will kill her next time. After the Sisters of the League leave, a wounded Tabitha is approached by a man who is associated with the League of Shadows. He claims that his part of the group are still loyal to Ra's al Ghul. When Tabitha asks if Ra's al Ghul is dead, he states that death is only an illusion. His fellow members then tranquilize Tabitha and load her into their car.
- † Ra's al Ghul (leader)
- † Sensei (second-in-command)
- † Anubis (tracker)
- † The Hunter (hunter)
- † Unnamed Captain
- † Palden
- † Sisters of the League (defected)
- Bruce Wayne (manipulated)
- Jeremiah Valeska
- Delta Force
- In the comics, the League of Assassins (which has also been called the League of Shadows in different media appearances such as Christopher Nolan's Dark Knight Trilogy) is an organization that is led by Ra's al Ghul and have their own plans to preserve the world their way. The recent Detective Comics series under the Rebirth inititative in fact introduced The League of Shadows as a mysterious sub-group within the League of Assasins.
- The League of Assassins bears striking resemblance to the Hashshashin, a Medieval Levantine Order of trained combatants and assassins who fought during the Crusades and were also lead by a mysterious and enigmatic mentor called the "Old Man of the Mountain."
- Cannon, Danny (writer) & Hope, Nathan (director) (June 5, 2017) "Heroes Rise: Destiny Calling" Gotham. Season 3. Episode 21. FOX.
- Lilien, Steven & Wynbrandt, Bryan (writer) & Tonderai, Mark (director) (October 5, 2017). "A Dark Knight: They Who Hide Behind Masks". Gotham. Season 4. Episode 3. FOX.
- McKenzie, Ben (writer) & Fink, Kenneth (director) (October 13, 2017). "A Dark Knight: The Demon's Head". Gotham. Season 4. Episode 4. FOX.
- Chun, Tze (writer) & White, Scott (director) (October 19, 2017) "A Dark Knight: The Blade's Path". Gotham. Season 4. Episode 5. FOX.
- Huston, Charlie (writer) & McKenzie, Ben (director) (March 29, 2018) "A Dark Knight: One of My Three Soups". Gotham. Season 4. Episode 16.
- Cannon, Danny (writer) & Copus, Nick (director) (April 12, 2018) "A Dark Knight: That's Entertainment" Gotham. Season 4. Episode 18.