- In the 1860s, US sailors intercepted 3 slave ships carrying over 1,400 African slaves bound for Cuba to be sold. The slaves were taken to Key West for 3 months and then returned to Africa.
- In the 1890s, Cuban guerrilla chief Maximo Gomez refused to operate in the Zapata region during Cuba's war for independence from Spain.
- In the 1940s and 1950s, American mafia figures like Meyer Lansky partnered with Cuban leader Fulgencio Batista to gain control over casinos, drugs, and prostitution in Cuba. This alliance gave the mafia significant influence over the country.