Salinger had gotten 1,200 Petit Upmanns, among the best of Cuban cigars, which he handed to Kennedy.

Winston Churchill, who loved to dunk his cigars in port wine or brandy, dressed an iconic figure during World War II, holding a cigar in his hand. In more recent times, former president Bill Clinton was known to have enjoyed smoking cigars, although this is a pleasure now denied him out of concerns for his health.

Aside from Cuban cigars, President Kennedy is known to have enjoyed Philippine cigars, probably the Alhambra brand, one of the mildest cigars made by the Philippines’ largest cigar maker, La Flor de la Isabela. President Kennedy’s favorite Cuban cigar was the Petit Upmann, also considered a mild to medium kind of cigar.

In an article published in 1996 in Cigar Aficionado, entitled “Cigars & Che & JFK,” Richard Goodwin, who served in the Kennedy and Johnson Administrations and who was instructed by Kennedy to draw up the executive order invoking the Trading with the Enemy Act against Castro’s Cuba, tells of a little-known incident involving Che Guevara and President Kennedy.

In August of 1961, there was a meeting of all the American nations at Punta del Este, a seaside resort in Uruguay. It was there that Richard Goodwin met Che Guevara. Aware of Kennedy’s preference for Cuban cigars, Guevara gave Goodwin two cigar boxes, one for him and the other for Kennedy.

The cigar box for Kennedy was inlaid with the Cuban seal and had a note to Kennedy in Spanish which said, “Since I have no greeting card, I have to write. Since to write to an enemy is difficult, I limit myself to extending my hand.” The note was signed “Che” over the typewritten “Comandante Ernesto Che Guevara.”

President Kennedy is just one of many famous historical figures who loved to smoke cigars.

Further details of Kennedy’s predilection for Cuban cigars are detailed by Salinger in an article published in 2002 in Cigar Aficionado. Several months after the Bay of Pigs fiasco in April 1961, President Kennedy called Pierre Salinger to his office and told him that he needed some help. Always solicitous, Salinger asked him what he wanted. “I need a lot of cigars, Pierre,” Kennedy told Salinger.

“How many do you need, Mr. President?” asked Salinger. “About 1,000 Petit Upmanns,” said Kennedy. When told that Kennedy needed them by the next morning, Salinger shuddered, knowing how difficult it would be to get them. However, being a cigar aficionado himself, Salinger knew of places where he could obtain them.

So the next morning, as soon as he arrived in his office, he was called by Kennedy, who asked him how he had done on his errand. “Very well, Mr. President,” answered Salinger. He had gotten 1,200 Petit Upmanns, among the best of Cuban cigars, which he handed to Kennedy.