The Good Life

Two Romeo y Julieta Cigars From Winston Churchill Sell For Thousands

A pair of old cigars gifted to an immigration officer from Churchill himself went on the auction block
Aug 21, 2023 | By Garrett Rutledge
Two Romeo y Julieta Cigars From Winston Churchill Sell For Thousands
Photo/Popperfoto/Getty Images

There are few figures in history who embodied the spirit and passion of cigar smoking more than Sir Winston Churchill. The revered statesman always had a cigar (or several) on his person—and occasionally, he’d give them away. This is apparently what happened during a trans-Atlantic voyage aboard RMS Queen Mary. Churchill not only gifted a pair of Romeo y Julietas to a first-class immigration officer, but a signed photo as well. Understanding the magnitude of the gift, the officer held on to the two smokes and the picture, all of which sold at an auction in a single lot for $5,500 on August 16.

Churchill

Along with the cigars and the picture, the auction lot included a letter of provenance from the son of the original recipient as well as a photograph of two unidentified men, one of whom is likely the immigration officer in question. The letter adds welcomed context to the artifacts. It was noted that this ocean liner was the primary method for travel between the United Kingdom and United States before the aviation boom. Before arrival to Southampton, England, passengers would need to be “processed” by the immigration officers, which is evidently where the officer, referred to as Wilfred Chalmers in the letter, received the cigars and picture after impressing Churhchill with his service.   

Churchill

It’s not clear when exactly this voyage took place, however, according to the International Churchill Society, Sir Winston crossed the Atlantic aboard the RMS Queen Mary three times during World War II. 

The two Romeo y Julietas are quite paradoxical to one another. The smaller cigar, measuring 4 3/4 inches long, comes housed in its original Romeo y Julieta tubo and remains in remarkable condition. Its companion, 6 1/2 inches in length, has seen better days, displaying clear signs of wear and tear.

Churchill

Other items from the recent Fine Autograph and Artifacts auction by RR Auction included a band-signed vinyl of Queen’s 1973 self-titled debut album (sold for $39,178), a Hollywood autograph collection featuring over 6,500 signatures (sold for $124,781) and a handwritten letter by Marie Antoinette to an Austrian ambassador (sold for $18,750). To see more, visit rrauction.com.

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