Gambol was a crime boss in Gotham City. After the mob had some of their money stolen by the Joker, Gambol met with other mob members to listen to a proposal from Mr Lau to keep all of their money in one place. After his proposal was finished, the Joker turned up in person and began taunting the men in the room. Gambol, angry at the Joker, ordered one of his men to kill the clown but the Joker impaled the man head-first on a pencil. Once the Joker had finished his proposal of killing Batman in exchange for half the mob's money, Gambol got up to deal with the Joker himself. He was stopped when the Joker threatened to blow himself up, but Gambol exclaimed that he was putting a bounty of $500,000 on the Joker's head, or double if he was kidnapped alive.
A short while later, Gambol's bodyguards told him that some bounty hunters had turned up claiming to have killed the Joker. They brought the body inside, and Gambol was about to pay them when he came alive and stabbed two of Gambol's henchmen. The Joker then held Gambol at knifepoint and told him a story about how his abusive father had sliced his face. He then cut Gambol's face in two, and dropped the body to the floor. Gambol's 3 remaining bodyguards then fought each other for a place in the Joker's operation.