Five people have owned the world’s most valuable and pedigreed cigar: a statesman, an auteur, a star. . . and two schmucks.

In the ’50’s, Sir Winston Churchill received Cecil B. DeMille at his home in Hyde Park Gate, during which one of the twentieth century’s most iconic leaders presented the megalomaniacal film director with a Santa Maria presidente size cigar in an aluminum tube — a tubo, in cigar parlance. The meeting was so memorable that DeMille detailed the encounter, and the gift, in his autobiography.

Alas, C.B. was not a cigar-smoker, so the tubo rested neatly on a pen-and-ink stand on his desk until 1988, when the contents of the DeMille Estate were auctioned off at Christie’s East. The cigar was bought by an unknown bidder, who five short years later auctioned it off again at Bonhams & Butterfields (then Butterfield & Butterfield). Aaron Sigmond, founding editor of Smoke magazine and publisher of The Cigar Report, snapped up the prized stick after a modestly protracted bidding war with another paddle-happy cigar fiend.

Although he built a museum-style plexiglass display case for the prize, Sigmond’s custody of the historic stogie was rather fleeting — in what would incite a never-ending case of seller’s remorse, he sold the cigar to an acquaintance, Whoopi Goldberg, who was then actively assembling a world-class cigar collection. While neither party will disclose the price paid for the cigar, it nonetheless remains to date the most costly single stick ever sold — well beyond any recorded at auction.

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