In the 1920s, ambitious but smalltime thief Jack Diamond and his sickly brother Eddie Diamond move to New York City. Jack meets dance instructor Alice Shiffer, lies to her to date her and to steal a necklace from a jewelry store. After being incarcerated for a time, he works with Alice at her dance school while on probation. He then gets hired as bodyguard of infamous Arnold Rothstein who gives him the nickname Legs. His plan is to supplant Rothstein with the intention of stealing his bootleg, drugs and gambling businesses. After Arnold is murdered, Legs Diamond sells protection. When he travels to Europe with Alice on a vacation, he sees in the newspaper that the New York underworld has changed with the National Prohibition Act. Legs returns to America and confronts the syndicate, demanding a cut from their operations. He kicks Alice out of his life and turns to Monica, who betrays him. Hit men enter his hotel room and shoot him dead. In the final scene, as his corpse is being removed on a stretcher, Alice says he was loved by many but that he loved nobody.
Frank de Kova's role is only listed as "The Chairman" of the new crime syndicate. He was portraying Lucky Luciano, but as Luciano was alive at the time, it was decided not to name him specifically. The lead role was first offered to Robert Evans. When he turned it down Warner Bros. Television contract star Ray Danton took the lead. Evans also had turned down the lead for The George Raft Story that Danton also played. Danton reprised his role as Legs Diamond in Portrait of a Mobster.
Production
Boetticher said the only actors he truly hated in his life were Gilbert Roland and Ray Danton. He says he wanted to make film like The Triumph of the Will "about one of the most despicable men of all time, Adolf Hitler. So I want to make a picture about a miserable, no good son-of-a-bitch that when you walk out of the theater, you say, "God, wasn't he greatl" And then you take two steps, and you say, "wait a minute, he was a miserable son-of-a-bitch!" He researched the film, found out all Diamond had done "and when I went back to Warner's and told them everything I'd learned, they wouldn't let me make the picture! So we had to clean it up a bit. We had twenty-four days on that; it was a good picture. "
The film was remade as a musical entitled Legs Diamond which debuted on Broadway at the Mark Hellinger Theatre on December 26, 1988, and closed on February 19, 1989 after 64 performances and 72 previews.
