Sydney Pollack directs Robert Redford as Jack Weil, a high-rolling poker player who is trying to make a big score in 1958 Havana, a pleasure seeker's paradise on the verge of revolution. Although excited by the prospect of gambling in a risky environment, his plans are turned upside down when he stumbles into Bobby, the beautiful enigmatic wife of Arturo Duran, an impassioned revolutionary, resulting in a move that threatens his last chance for the big score.