Fidel Castro was ruler of Cuba when Kennedy became President, was still ruler during the entire Kennedy Presidency, and remained ruler long after Kennedy died.
Deliberately deceived by the CIA into thinking it would work, Kennedy authorized an invasion of anti-Castro rebels into Cuba. It was a complete and total failure, as the CIA knew it would be, but Kennedy did not follow this up with explicit US Military support.
In other words, Kennedy WANTED Castro to be overthrown, but realized it could not be done without major repercussions.
So far as I know, Kennedy is the only one who made any real effort to overthrow Castro when he endorsed the ill-fated Baty of Pigs invasion.
President John F. Kennedy did not personally overthrow any leaders, but he was involved in the U.S. government's covert operations aimed at overthrowing Fidel Castro in Cuba. The most notable operation was the failed Bay of Pigs invasion in April 1961, which sought to oust Castro's government but resulted in a significant defeat for U.S. forces. Kennedy's administration also engaged in various efforts to undermine Castro's regime during his presidency.
because he was on crack
Many consider John F. Kennedy's biggest failure to be the Bay of Pigs invasion. The planned covert operation to overthrow Fidel Castro's regime in Cuba was poorly executed and ultimately resulted in failure, damaging the credibility of the United States and Kennedy's administration.
Land on the moon, get rid of Castro, supported Dr. King.
CIA plot in 1961 to overthrow Fidel Castro by training Cuban exiles to invade and supporting them with American air power. The mission failed and became a public relations disaster early in John F. Kennedy's presidency.
John F. Kennedy January 20, 1961
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John F. Kennedy was in the Navy
What did John F. Kennedy do as a kid