Robert Redford as Jack Weil; Lena Olin as Bobby Duran; Alan Arkin as Joe Volpi; Tomas Milian as Menocal; Daniel Davis as Marion Chigwell; Tony Plana as Julio Ramos; Betsy Brantley as Diane; Lise Cutter as Patty; Richard Farnsworth as Professor; Mark Rydell as Meyer Lansky; Vasek Simek as Willy; Fred Asparagus as Baby Hernandez; Richard Portnow as Mike MacClaney; Dion Anderson as Roy Forbes; Carmine Caridi as Captain Potts
An American professional gambler named Jack Weil (Redford) decides to visit Havana, Cuba to gamble. On the boat to Havana, he meets Roberta Duran (Olin), the wife of a revolutionary, Arturo (Julia). Shortly after their arrival, Arturo is taken away by the secret police, and Roberta is captured and tortured. Jack frees her, but she continues to support the revolution.