When Oswald Cobblepot convinced James Gordon that the only way to make sure Theo Galavan is defeated is to kill him, they locked Theo into the trunk and took him to the Southside Docks. Theo said Jim is a man of principle and predicted that he will regret this. However, Jim explained he has many regrets, but this won't be at the top of the list. Resigned to his fate, Theo kneeled before Oswald and Jim and lamented that it will be a beautiful morning. Theo bid Jim goodbye, whereon Oswald started beating him mercilessly with a baseball bat as vengeance for his mother Gertrud's murder. Theo begged Jim to kill him, and Jim shot him through the chest. Oswald then pushed one of his umbrellas down Theo's throat, as Jim walked away. After his death, Theo's body was taken from the morgue to Indian Hill to be experimented on by Professor Hugo Strange.
- "Rise of the Villains: Worse Than A Crime"
- "Wrath of the Villains: Mr. Freeze" (flashback)
- "Wrath of the Villains: Into the Woods" (mentioned)
- Chapter 4 (flashback)