In February 1962, the United States was on the precipice of formalizing the Cuban trade embargo. Before the President could put pen to paper on the executive order that would sever ties with the island for decades, he issued a specific, urgent command to his Press Secretary, Pierre Salinger.

The mission was simple but daunting: Kennedy needed as many H. Upmann Petit Coronas as he could find by the next morning. Salinger, a man who understood the "big hello" of Washington life, spent the night scouring every humidor in Washington. When he walked into the Oval Office the following morning and confirmed the successful haul, 1,200 cigars. Kennedy reportedly smiled, opened his desk drawer, and signed the embargo into law.

Kennedy’s choice of the H. Upmann Petit Corona was a reflection of his broader sensibilities, devoid of unnecessary flourish. While many of his contemporaries favored the massive, imposing "Churchill" vitolas, JFK preferred a smaller, unimposing cigar. The Petit Corona offered a refined profile that fit the brisk pace of the man leading the United States through a tumultuous period in history.

Whether he was photographed on the deck of his sailboat the “Honey Fitz” or leaning over a map in the Cabinet Room, the presence of the cigar served as a marker of Kennedy’s composure. It suggested that despite the weight of the world, he could still find a moment for himself.