1958: Gambler Jack Weil (Robert Redford) meets a woman, Bobby Duran (Lena Olin), on a boat bound for Havana. She is working for Castro's rebel forces, who are attempting to overthrow the Batista Government. Jack agrees to help her with some smuggling, but he then continues on his way, hoping to set up a high-stakes card game. When he and Bobby meet again, however, he is asked to become more involved in the cause.
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