There is no better businessman than the one who falls in love with a product, and then makes it his life’s work to bring that same joy to other people. Such is the story of Michael Cafagno, owner of the luxury cigar retail shop The Tobacconist of Greenwich.

“I got into this business by mistake,” recalls Cafagno, relaying the tale of how he came to unofficially inherit The Tobacconist from Jimmy “Cigars” Lacerra, founder of the shop and Cafagno’s mentor and teacher. After being introduced to Jimmy by a mutual friend, Cafagno was initiated into the world of high end cigars at the age of 19, and he was hooked.

Cafagno stopped by the shop every day after that first introduction, and Jimmy eventually hired him to work part-time while he taught Cafagno the business and culture of the cigar world.

“He taught me how to balance a checkbook and maintain relationships with some of the world’s most powerful people,” Cafagno recalls. “He taught me loyalty, he taught me respect, and most importantly, he taught me that if you say something, you do it.”

The importance of follow through and staying true to your word was how Cafagno came to inherit the shop from Jimmy upon his death in 2011. A conversation over lunch and a handshake was all it took for the two men to decide the fate of The Tobacconist. “You keep doing a good job…[and] you’re going to take this place over and take care of my wife,” Jimmy told him, and that was that. No lawyers, no contracts and the proposition was never discussed again. When Jimmy Cigars passed in June of 2011, Cafagno took the place over and has been running it ever since.

The success of The Tobacconist in Cafagno’s hands can be seen in the prestigious awards the shop has racked up over the years, most notably with the luxury cigar brand Davidoff of Geneva. The Tobacconist of Greenwich has won five of Davidoff’s Golden Band awards since 2012, including the prestigious Appointed Merchant of the Year award in 2015. In 2021, in addition to the 4th Best Performance in a Single Location Golden Band Award, The Tobacconist of Greenwich was nominated into the Davidoff Hall of Fame.

“Davidoff is the greatest company in the world!” Cafagno claimed in a recent interview with Tobacco Business. “I don’t just say that because of my relationship with them; I say that because the people who run the company have the same values I have,” he explains. They’re a loyal, respectful group of businesspeople who have honor, vision, and a genuine interest in the success of the shop.

Personal relationships are the core foundation of the The Tobacconist of Greenwich. All encompassing cigar experiences are what we strive to create for our customers every day. In essence, imprinting a lifelong memory for each of our clients has become our mission and key to our ongoing success. Cafagno’s mission in life has become to carry on the legacy of Jimmy ‘Cigars’ Lacerra, to allow each and every client that walks through his doors to feel the genuine heritage and history of the Tobacconist of Greenwich.

Michael’s Picks

Try one of Michael’s favorite cigars.

Davidoff Royal Release Salomones

What do former NBA star Michael Jordan, Rush Limbaugh, Sidney Frank, and the Tobacconist of Greenwich have in common: they have all laid hands on Marvin’s Mystery Box, the limited edition Elie Bleu humidor. This coveted humidor brought in over $1.8 million at a charity event in 2005 when it sold as a triple lot of humidors to Jordan, Limbaugh, and Frank. Now, the very humidor purchased by Sidney Frank that record-breaking night in April is currently at the Tobacconist of Greenwich, awaiting auction.

The legendary humidor already enjoyed the unofficial title of crowning jewel of the annual Night to Remember charity auction, hosted at the Four Seasons restaurant. Held for over 20 years now, Night to Remember is hosted by the editor and publisher of Cigar Aficionado magazine Marvin Shanken, with all proceed going to the Prostate Cancer Foundation.

Marvin’s Mystery Box was the capstone of Night’s auction in 2005, brought out after 18 other items were featured; items that included a collection of 693 Fuente-made cigars that included every Fuente Fuente Opus X, a trip for 10 on 141-foot luxury yacht in the Caribbean, and a chest filled with 100 bottles of rare wine. Yet even amidst this stunning lineup, Marvin’s Mystery box was held until the very end as befitting its station, after the Paradis Cognac was poured and the dinner cigars were lit.

The cedar-lined sycamore humidor, trimmed in ebony and inlayed with yellow sycamore is filled with unknown treasures and adorned with genuine Cuban cigar bands. It stands as the only non-cigar object that the Cuban government has allowed to be decorated in such a way. While the contents of the Mystery Box have never been divulged, it has been strongly hinted that it contains a trove of genuine Havanas.

The bidding started that night at a reasonable $50,000 and was headed toward a respectable mid $100,000 sale in Sidney Frank’s favor until Michael Jordan intervened. Well known for his appreciation of high-end cigars, Jordan and his tablemate, Rush Limbaugh, soon drove the price to the high $200,000’s as they played off each other in a three way bidding war. Shanken, recognizing the historic implications of the auction when the bidding hit $270,000, offered the trio a deal: he would triple the lot if each man agreed to pay $300,000 for a box. The total amount was then doubled by financer and cancer survivor Michal Milken, bringing the total sale to $1.8 million.

Now, the chance to walk the same historic paths as the men who inspired greatness in spirits, sports and politics is at hand. The bidding for Marvin’s Mystery Box will take place at a date to be announced in 2022, with an opening bid of $300,000. Interested parties should go to our auction below. Sign up for our newsletter to receive information about this auction.

Link to article detailing the historic auction can be found here.

Go to our Auction page

to place your bid before July 28, 2022 8:00pm.