Fulgencio Batista

Batista surfaced in the 1933 Revolt of the Sergeants, appointed himself colonel, and ran Cuba through puppet presidents until winning the presidency outright in 1940 on a populist platform - then left for Florida when his term ended in 1944. He returned in 1952 to run again, but facing certain loss, seized power in a military coup instead. This time he suspended the constitution he'd once installed, aligned with wealthy landowners and U.S. sugar interests controlling most of the island, and cut deals with the Mafia to profit from Havana's vice trade. As discontent grew, his secret police carried out systematic torture and executions - estimates range from hundreds to 20,000 dead by the time revolutionary forces under Fidel Castro and Che Guevara defeated his army at Santa Clara on New Year's Eve 1958. He fled to the Dominican Republic the next day, eventually settling in Portugal, where he died in 1973.