Monk Eastman: The Sheriff of the Street

The leader of the Eastman Gang, he was the toughest thug in turn-of-the-century New York.

• Gang Wars: He commanded an army of over 1,200 gangsters and fought violent turf wars against the Five Points Gang.
• The War Hero: Surprisingly, he enlisted in WWI at age 42 and returned a decorated hero, regaining his citizenship.
• The End (1920): His redemption was short-lived; he was shot five times by a corrupt Prohibition agent during an argument.