Fidel Castro entered Havana in January 1959 and later transferred power to his brother Raúl in 2008. Fidel Castro died in 2016, Raúl Castro retired in 2021 at age 94, and the Cold War ended 35 years ago with the Soviet Union's collapse. Analyses from progressive, conservative, libertarian, and devil's advocate viewpoints address implications for current U.S.-Cuba relations.