In the vibrant yet decaying atmosphere of Havana in 1958, a professional gambler named Jack Weil finds himself caught between the pursuit of fortune and love in a country engulfed in political upheaval. Portrayed by the charismatic Robert Redford, Jack becomes the center of a love triangle when he meets a beautiful Cuban woman, played by the enigmatic Lena Olin. As a connection blossoms between them, their personal stories begin to intertwine with the impending revolution that will shake the island.
Jack's life becomes even more complicated as he confronts the brutality of Batista's government and the rising influence of Fidel Castro. As his passion for life and gambling leads him to stake his fortune, the political tension serves as a dramatic backdrop that not only impacts his romantic relationship but also his life-altering decisions. The vibrant settings of Havana, with its infectious music and atmosphere of revelry, contrast sharply with the grim reality of a nation on the brink of change.
With a script that weaves together romance, action, and a sense of urgency, Jack must decide between the allure of a life without constraints and a commitment to an uncertain future. As the echoes of revolution grow louder, he will face the question of whether love and freedom can coexist in such a tumultuous world.