The seventh teaming of Robert Redford and director Sydney Pollack, and the first since 1985's Best Picture Oscar winner OUT OF AFRICA, opens late in 1958 with gambler Jack Weil (Redford) sailing for the then wide-open city of Havana. On board, he meets the lovely Bobby Duran (Lena Olin)
and immediately falls for her. Bobby is somehow involved with the revolution which is taking place in Cuba, siding with the rebel forces led by Fidel Castro against the incumbent government under the rule of Fulgencio Batista. Though Jack is not the least bit political, he chivalrously agrees to
help her do some smuggling to aid the rebels. Once in Havana, they go their separate way...