The film is set on the eve of the Cuban Revolution's victory. On Christmas Eve, 1958, aboard the boat from Miami to Havana, Roberta Duran (Lena Olin) enlists the aid of Jack Weil (Robert Redford) in smuggling U.S. Army Signal Corps radios destined for the revolutionaries in the hills. Weil agrees only because he is romantically interested in her. When they rendezvous for the "payoff," Roberta reveals that she is married, dashing Weil's hopes. In Havana, Weil meets up with a Cuban journalist acquaintance (Tony Plana) and during a night on the town, they run into Roberta and her husband, Dr. Arturo Duran. Duran (Raúl Juliá) is a Revolutionary leader. When Roberta points Weil out to him, Duran invites Weil to join them for dinner and asks Weil for further aid to the cause. Weil turns him down, even after Duran outlines the desperate situation confronting the Cuban majority.
The next morning, after a night of debauchery for Weil but one of police arrests for the revolutionaries, Weil reads a newspaper account of Duran's arrest and death. In shock, he continues with the planned poker game, coincidentally meeting the head of the secret police. He learns that Roberta was also arrested and tortured in custody. He pressures another player in debt to him to obtain her release. Shaken by her husband's death and her own experience in jail, she agrees to let him shelter her in his apartment but disappears that afternoon.....
Directed by Sydney Pollack
Produced by Sydney Pollack
Richard Roth
Written by Judith Rascoe
David Rayfiel
Starring
Robert Redford
Lena Olin
Alan Arkin
Music by Dave Grusin
Cinematography Owen Roizman
Edited by Fredric Steinkamp
William Steinkamp