James "Jimmy" Peake, a.k.a. Jazzman, was a gangster in Gotham City. He seemed to be more of an ordinary criminal as opposed to "theme villians" like Joker or Riddler, although he did use a Thompson submachine gun and peppered his speech with jazz terms and other musical anecdotes, suggesting the image of a 1920s gangster.
Six years later, Peake, now Jazzman, initiated a drug sale and lured the Police Department into a trap. When Gordon was set to get Jazzman, he was severely wounded and taken to the hospital as Batman subdued the gangster.
Due to Gotham City Jail being overcrowded at the time, Judge Maria Vargas sentenced Jazzman to Stonegate Penitentiary to await trial. However, Jazzman escaped and instead of fleeing, he went straight to Gotham Hospital to finish off Gordon. Fortunately, Batman intervened and a brutal fight ensued between the two vengeful foes. Jazzman would have finished Gordon off had it not been for Batman destroying the gun at the final moment with a well-aimed Batarang. Harvey Bullock arrived and immediately arrested the Jazzman.