A Gentleman of History: Winston Churchill
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And it was in the Caribbean that Churchill's cigar smoking began in earnest. Having arrived in Havana in November 1895, along with a fellow officer named Reginald Barnes, and having been stood up at the docks by the Spanish commandant who was to have met the two men, Churchill and Barnes took a room at one of the best hotels in town and spent the next several days living off of little more than two of the local specialties, oranges and cigars. From that point on, Churchill favored Cuban cigars above all others.