US President John F. Kennedy, who left behind a 50-year legacy of frozen relations between Washington and Havana, led his nation at a moment in history when Cuba took the Cold War to America's doorstep.
From the Bay of Pigs invasion in 1961 to the Cuban Missile Crisis in October 1962, Americans were on the edge of their seats as Communism loomed ever closer and nuclear warheads seemed capable of raining from the sky.
Although Kennedy is associated with the invasion and crisis, it was his predecessor Dwight Eisenhower and CIA director Allen Dulles who formulated plans for a military intervention by Cuban exiles, which would become known as the Bay of Pigs invasion.
After Kennedy took office in January 1961, he gave the plan a green light on condition that it would not involve a direct American presence.
After training in Guatemala, some 1,400 exiled Cubans landed on April 17, 1961 on beaches along the Bay of Pigs, less than 200 kilometers (125 miles) southeast of Havana, with an end goal of halting Cuban leader Fidel Castro.
The invasion was a disaster on air and land. US bombers largely missed their targets. Castro's T-33 jets struck two US B-26 bombers, killing four American pilots.
And the surprise ground attack was easily thwarted after news leaked to Cuba and tens of thousands of militiamen led by Castro himself greeted the invading forces.
Fierce fighting lasted two days until the exiled Cubans threw in the towel on April 19 with 1,189 prisoners taken and 107 dead among their ranks, compared to 161 dead among Castro's forces.
The prisoners were paraded on television. Five officers were executed, nine were condemned to 30 years in prison and the others were freed in December 1962 in exchange for $53 million in food and medicine.
"The invasion was one of the major strategic errors of the United States in the 20th century, reinforcing Castro's control over Cuba, ensuring the permanence of his revolution and helping to drive him into the Soviet camp," said historian Richard Gott.
The following year, the Cuban Missile Crisis would clearly demonstrate the strength of the Cuba-USSR relationship.
Missile Crisis begins
In February, Washington strengthened its economic embargo against Cuba and the CIA continued to devise anti-Castro plans to destabilize Cuba under its Operation Mongoose.
Castro turned to Moscow to ensure protection, and a delighted Nikita Khrushchev convinced him that missiles fixed on the United States would be a better US deterrent than any military accord.
In October 1962, US spy planes spotted Cuba's new missiles.
Unable to tolerate the presence of a Soviet nuclear arsenal 150 kilometers from American soil, Kennedy warned Khrushchev of an imminent attack if the missiles were not removed.
The missile crisis reached its height between October 14 and 27, peaking on October 22 when Washington ordered a naval blockade of Cuba and the mobilization of 140,000 troops.
Castro, meanwhile, mobilized 400,000 troops in the event of an American invasion.
Without consulting the Cuban leader, Khrushchev on October 28 conceded the removal of missiles in exchange for a US promise to not invade Cuba. Covertly, Moscow also negotiated the removal of US missiles from Turkey.
The agreement fell short of Castro's desires, which included an end to the US embargo and anti-Castro activities, a halt to airspace violations and the closure of the US military base at Guantanamo Bay.
It did not, however, prevent Cuba and the USSR from operating in close concert during the next 30 years, as Washington abandoned its military designs on Cuba.