Gambol

"I'm putting the word out. Five hundred grand for this clown dead; a million alive, so I can teach him some manners first."

- Gambol

Gambol was one of Gotham City's crime lords. He was the head of a Black mob in Gotham City.

History
Gambol's gang was at a turf-war with the Italian mob, led by Sal Maroni, and the Russian mob, led by The Chechen. Since the arrival of Batman, Gambol had made a truce with Maroni and the Chechen and formed an Alliance with the other crime organizations as Batman had become a threat.

He acquired an immediate hatred of the Joker, who arrived unannounced to a business meeting between the mob and repeatedly insulted him. Gambol was also displeased with the fact that the Joker stole money from the mob's bank. The Joker also managed to slam one of Gambol's guards head into a pencil, killing him instantly.

Gambol's empire toppled
After placing a bounty on him, Gambol was tricked by a trio of bounty hunters who made it seem like they brought him the Joker dead. The Joker revealed himself alive after stabbing two of Gambol's men with knives, pressed a knife in Gambol's mouth, and told him an ambiguous story of how he got his scars.

Gambol's empire was destroyed for good after the Joker made his last surviving men fight to the death with half of a broken pool stick.

Behind the scenes

 * The exact manner in which the Joker injured Gambol is currently ambiguous. He may have stabbed him in the side of the head or neck. Another possibility is that he slit Gambol's throat or mouth. The Joker may have also inflicted an extreme "Chelsea Grin" on one side, passing the knife between Gambol's jaw and skull, and into the base of his brain.
 * "Gambol" means "To frolic or dance about". As Gambol would likely never accept this as a nickname or alias, Gambol was likely his last name. It also could have been derived from the word "gamble".
 * Gambol is played by Michael Jai White, who was best known for playing superhero Spawn. Both Spawn and Gambol share a mutual hatred for clowns (Joker, Clown/Violator).