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Jack Diamond and his sickly brother arrive in prohibition New York as jewel thieves. After a spell in jail, the coldly ambitious Diamond hits on the idea of stealing from other thieves himself and sets about getting close to gangster boss Arnold Rothstein to move in on his booze, girls, gambling, and illicit drug operations.
In the 1920s, the ambitious small-time thief Jack Diamond and his ill brother, Eddie, arrive in New York. Jack meets the dance teacher Alice Shiffer and uses dirty tricks to date her and steal a necklace from a jewelry store. After a stint in prison, he goes to work for Alice in the dance school during his probation. Then he decides to work as a bodyguard for the powerful gangster boss Arnold Rothstein (who dubs him "Legs") with the intention of taking over his illegal business of bootleg booze, drugs and gambling. When Rothstein is murdered, Legs Diamond sells protection to other gangs. While vacationing in Europe with Alice, he reads in the news of changes in the New York underworld with the Volstead Act enacting Prohibition and returns home to find a different city - one that he no longer understands.
Ray Danton
Jack 'Legs' Diamond
Karen Steele
Alice Scott
Elaine Stewart
Monica Drake
Jesse White
Leo 'Butcher' Bremer
Simon Oakland
Lt. Moody
Robert Lowery
Arnold Rothstein
Judson Pratt
Fats Walsh
Warren Oates
Eddie Diamond
Frank DeKova
Syndicate Chairman
Gordon Jones
Sgt. Joe Cassidy
Joseph Ruskin
Matt Moran
Dyan Cannon
Dixie
Richard Gardner
Vince Coll
Don Anderson
Bartender
Sammy Armaro
Cab Driver
Herb Armstrong
Cherry Nose Gioe
Nesdon Booth
Pawnbroker
George Bruggeman
Nightclub Patron
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