Thomas Schiff was a paranoid schizophrenic and a former patient of Arkham Asylum. He was attracted to work for the Joker, an anarchist who wanted to cause chaos in Gotham, and Schiff was part of the Joker's plan to assassinate Mayor Anthony Garcia. At the memorial service for Commissioner Gillian Loeb, Schiff and the Joker's other men tied up the honour guard and took their clothes and weapons. Schiff's name badge was switched to "Rachel Dawes", as a threat of the Joker's next victim.
Schiff, the Joker and his other men then attended the funeral dressed as the honour guard and fired a gun salute. As soon as a window blind flicked up, distracting the police snipers, the men then fired at the mayor. James Gordon took a bullet, protecting Garcia, and Schiff was apprehended by police officers. He was taken to an ambulance to dress his wounded leg, but Harvey Dent appeared and asked him where the Joker was. Schiff didn't respond, so Dent kidnapped him in the ambulance and drove him to a secluded location.
Dent then threatened to kill Schiff if he didn't reveal the Joker's location. He flipped a coin, telling him he would kill him if it landed on tails. Before he could flip it twice, Batman appeared and talked Dent out of the interrogation.