By Oliver Bennett • February 28, 2026 • Share
However, the decision came with an unexpected twist. Aware that Cuban cigars would soon be prohibited, Kennedy discreetly asked his press secretary, Pierre Salinger, to procure as many as possible before the embargo took effect. The following morning, Salinger returned with about 1,200 Petit Upmanns, Kennedy’s preferred brand. Only then did the president officially authorize the embargo, which would freeze trade and diplomacy between the two countries.
This embargo was part of a larger Cold War strategy. Following the failed Bay of Pigs invasion and escalating tensions with Fidel Castro’s communist regime, the U.S. aimed to isolate Cuba both economically and politically.
The ban emerged as one of the most lasting symbols of U.S. foreign policy during this period, enduring well beyond Kennedy’s time in office. Yet, the image of JFK savoring a cigar while simultaneously denying Americans access to the same luxury stands out as one of the most ironic and relatable moments in Cold War history.
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