Michael Cafagno

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