If there was a place where England touched the Caribbean Sea, where FDR and JFK sat down with Fidel Castro and Che Guevara, where Arnold Schwarzenegger had a meeting of minds with Winston Churchill, they would serve cigars. Far-fetched perhaps and not on any map, it would be the place where powerful leaders went to take a private moment away from the pressure of politics.

Of course, one of the most famous cigar smokers ever to have lived was Winston Churchill. A thinker and writer as well as a politician, Churchill was known for his aphoristic wit and his leadership during the dark days of WWII. Perhaps no politician before or since has been more committed to his cigar. Legend has it that he had a special oxygen mask made so that he could continue to smoke on high-altitude flights.

The world of cigar honours him to this day. A Churchill cigar refers to a large cigar normally around 17cm in length and with a 48-50 ring gauge, a mighty cigar to suit a larger than life man.

Cigars have been front and centre of political machinations ever since. Fidel Castro was synonymous with cigars for many years. Whilst planning the overthrow of the Batista regime, Castro would say that the only time they did without cigars was when they ran out. As supplies ran low, he would hoard his last smoke, waiting for a victory to warrant it. His colleague-in-arms, Che Guevara took up cigar smoking embracing the customs of his adopted land, Cuba. His two indulgences were books and cigars, anything else he could do without.

Given the iconic status of cigars in the Cuban halls of power, they could hardly fail to have political significance across the water in America.

Compelled to impose a trade embargo, John F Kennedy couldn’t bring himself to prohibit the importation of his favourite luxury smoke without stocking up. Given just a day to procure them, press secretary, Pierre Salinger located and stashed 1,200 Petit Upmanns so that JFK could sign the embargo on all Cuban imports.

Cuban cigars continued to be formally off-limits in the US for more than 40 years although they retained a cult status akin to bootlegged rum during prohibition. Passed quietly around gentleman’s clubs and the halls of power, they nevertheless remained illegal until the election of President Obama.

Part of a program to relax trade restrictions on Cuba and rebuild cordial relations with its near-neighbour, sanctions were lifted in 2016. Although no doubt geopolitics were the primary motivation for the change in the law, Obama has been known to enjoy a quiet cigar himself. One can imagine him quietly bringing the aroma of a good Cuban back to the White House.

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