In view of the changing relationship between Cuba and the USA, this paper explores the activities of the American entrepreneur Milton Hershey in Cuba during the first half of the twentieth century and a long-lasting impact that these activities left both on the Caribbean island and back home in Pennsylvania. Biographical, social, cultural and artistic issues will be discussed and analyzed. In search of control over a sugar supply for his chocolate production, American industrialist Milton Hershey spread his chocolate empire far beyond his Pennsylvania homestead. He built a highly efficient sugar mill and a refinery in Cuba that were eventually connected to the rum production during Prohibition. The Cuban enterprise included the first elec...