Jack Weil (Robert Redford), a professional gambler, enjoys the hedonistic lifestyle of Batista's Cuba, where he is organizing a crucial poker game that could make or break him. He meets seductive Bobby Duran (Lena Olin) and is surprised that she, a wealthy woman, is aiding Fidel Castro and his communist rebels. Apolitical Jack doesn't usually take sides, but after Bobby and her husband, Arturo (Raul Julia), are arrested, he contemplates risking everything to help their cause.