Following Cuba's turn toward the Soviet bloc and the failed Bay of Pigs invasion, Kennedy expanded existing restrictions into a comprehensive embargo banning nearly all trade with Cuba. The order, issued under the Foreign Assistance Act, effectively sealed off the island from American commerce. Decades later, remnants of the embargo remained among the longest-running trade sanctions in modern history, still debated in U.S. politics into the 21st century.
Tensions between Washington and Havana had escalated steadily since Castro's 1959 revolution, nationalization of American-owned businesses, and growing alignment with Moscow. The failed CIA-backed Bay of Pigs invasion in April 1961 hardened attitudes on both sides, and by early 1962 the Kennedy administration decided a full economic blockade was the next escalation short of military action.
Kennedy's proclamation banned virtually all trade between the two countries, building on partial measures imposed by Eisenhower in 1960. It was timed strategically — reportedly delayed until after Kennedy secured a private shipment of 1,200 of his favorite Cuban cigars, according to journalist Pierre Salinger's famous, though disputed, anecdote.
The embargo would outlast the Cold War itself, tightened further after the 1962 Missile Crisis and codified into law by Congress in the 1990s. Generations of Cuban Americans, U.S. policymakers, and Cuban officials have since argued over whether it hastened or entrenched Castro's grip on power. It remains, with modifications, in effect six decades later, a strange fossil of Cold War geopolitics still shaping U.S.-Latin American relations.