Carrying the Torch | Tobacconist magazine

Carrying the Torch

The Tobacconist of Greenwich’s Michael Cafagno honors mentor Jimmy Lacerra

By Stephen A. Ross

When Michael Cafagno, owner of The Tobacconist of Greenwich, answered the store’s phone one Saturday around 5 p.m., he wasn’t expecting to receive a call from a frantic and weeping woman on the other end of the line. It was just two hours before her son’s wedding and reception, and in all the chaos of wedding planning she had forgotten one important detail—securing cigars for the celebration. Cafagno reassured her and told her that he would take care of it. He closed the store a little early that day so that he could personally deliver the needed cigars. The grateful woman thanked him profusely and the wedding celebration went off as planned, but to Cafagno, it was no big deal. In fact, it was just another example of treating his customers the way his mentor, former The Tobacconist of Greenwich owner Jimmy Lacerra, would expect.

“Jimmy taught me to please the customers without sacrificing integrity,” Cafagno says. “Our clientele base is loyal to us, and we in turn are nothing but loyal to them. The goal is to make people happy and to provide a service.”

The story of how the 29-year-old Cafagno is carrying on Lacerra’s legacy is one that could easily be turned into a Hollywood movie. Lacerra established The Tobacconist of Greenwich in Greenwich, Connecticut, in 1974. Born in 1942, Lacerra was an old-school throwback in every sense of the term. His was a commanding presence. He dressed well and always had his hair neatly in place. The artist LeRoy Neiman once mistook him for Frank Sinatra when Lacerra was having dinner at nearby Rao’s, which must have thrilled the son of Italian immigrants to no end. He held court inside his tobacco shop for nearly 40 years before his death in 2011, always providing visitors with great customer service in a courteous and stately manner. One of those customers was Cafagno.

IMG_8874Michael Cafagno

Cafagno was 19 at the time and had no idea what he wanted out of life. He worked three jobs as a waiter and was going to school. He was also supporting a very young daughter. Cafagno was a novice cigar smoker, picking up a few smokes every now and then from a newspaper stand. Following the suggestion from a chef at one of the restaurants where he worked, Cafagno visited The Tobacconist of Greenwich one day in the summer of 2006.

After ascertaining that Cafagno was old enough to purchase cigars, Lacerra asked him what he wanted. Cafagno really didn’t know. Lacerra then picked up a tray and started selecting cigars from his stock. Catching a glimpse at some of the price points of the cigars Lacerra selected, Cafagno almost fainted, but pride convinced him that he would look foolish if he backed out by then. The total was almost $500—more than a week’s wage for the young Cafagno—but he bought the cigars. Lacerra then invited him to come back in a week or so after he had a chance to enjoy the cigars to talk about them.

“I had no idea what I was smoking, but I liked every one of them,” Cafagno recalls. “I came back and told him that I liked everything he had picked out for me but I didn’t know why. We sat down and started talking. We hit it off. I looked up to him immediately because he had what I wanted—he was respected and he had a successful business.”

Cafagno became a regular customer, and about six months later Lacerra offered him a part-time job. Wanting to impress, Cafagno worked hard, always cleaning the store until one day Lacerra pulled Cafagno aside.


“He told me that part of this business was sitting down with your customers and talking to them,” Cafagno says. “He told me I didn’t have to clean all the time and that he wanted me to sit down and get to know the customers.”

It might not have occurred to Cafagno at the time, but Lacerra had thoughts about the young man’s future. When Cafagno graduated, Lacerra offered him a full-time job. Working with Lacerra every day, Cafagno learned more basics about running a tobacco shop—inventory management, proper ordering techniques and how to anticipate your customers’ needs. The arrangement was working so well for both parties that one day Lacerra discussed his future plans with Cafagno.
“We were having lunch, and he said to me that if I kept learning and kept my head on straight that I wouldn’t have to worry about my future,” Cafagno remembers. “He told me that when he died I was going to take over the store. His wife, Jacqueline, and I would be partners. If she needed anything, I would make sure she had it. I shook his hand and we never spoke about it again. Jimmy passed away on June 10, 2011. He was like a second father to me. I will always carry on his legacy. It’s his. He built this place up over 36 years. I came in at the end of a rainbow and am kind of extending it more and updating it for the 21st century.”

jimmy and michaelCafagno with The Tobacconist
of Greenwich founder Jimmy Lacerra

With Jacqueline’s blessings, Cafagno updated the store. He consigned an aquarium that Lacerra had kept in the shop to the trash heap and replaced it with a new accessory display case. Sales of S.T. Dupont lighters rose dramatically. The Tobacconist of Greenwich had been a longtime Davidoff Appointed Merchant, and Cafagno was one of the first in the United States to adopt its shop-in-shop concept, devoting an entire wall to nothing but Davidoff products.

“The shop-in-shop adds to the elegance of the store,” Cafagno says. “We’ve added some Davidoff humidors that retail for $7,000. They are elegant pieces of furniture that I can tell a story about. Previously we sold a lot of $1,500 humidors, but I’ve seen sales of those humidors almost double because of the more expensive humidors I stock. A customer might think that he can’t afford a $7,000 humidor, but then when I show him one that’s made by the same manufacturer with the same quality standards that’s significantly less money, they have an easier time buying it. Building more room to expand our selection were all things that happened in the first two or three years of taking over, and it’s all worked out well.”

It’s worked out so well in fact that The Tobacconist of Greenwich became one of Davidoff’s top retailers. At Davidoff’s annual Golden Band Awards, held during an exclusive dinner at the IPCPR show, The Tobacconist of Greenwich won the Best Performance (Single Location) award in 2012, 2013 and 2014. Last year, The Tobacconist of Greenwich was named Davidoff’s Appointed Merchant of the Year.

“It’s been a pretty amazing journey to share with them,” Cafagno says. “Hans-Kristian Hoesjgaard [Davidoff CEO] and Jim Young [president of Davidoff North America] have such innovative minds, and they took an already successful company and made it more successful. I love being a part of their evolution and appealing to the younger consumer. I brought Jacqueline out to the [IPCPR] dinner and she got to experience it. I try to include her in as much as we do so she can understand what Jimmy built.”

With the store updated to Cafagno’s liking, he cast about for other ways to expand the business. Talking one day with Davidoff’s Rich Krutick, he explored the possibility of opening a Davidoff Lounge in Greenwich.


“Rich told me that if I wanted to do it, they would make it happen,” Cafagno recalls. “I approached a friend of mine, Michael Stelluti, who had helped me plan events for The Tobacconist of Greenwich, to be a partner. When he agreed, I called Rich again and told him we were ready to go for it.”

A stand-alone lounge that’s nearly three times larger than The Tobacconist of Greenwich, the Davidoff Lounge is, as Cafagno describes it, a “country club for cigar smokers.” The Davidoff Lounge is supported solely by memberships and opened in August 2014.

“The place is going great. It’s a new business, and the model is different than most others because it’s a separate location from the store,” Cafagno says. “Davidoff is the brand that drives people to the place. Our membership is good and growing. It’s a blank canvas to create whatever we want. It’s been an exciting experience.”

That last sentence could sum up Cafagno’s life since he first walked into The Tobacconist of Greenwich and met Jimmy Lacerra. Lacerra’s tough-love approach instilled the confidence Cafagno needed at a critical turning point in his life. That confidence has allowed Cafagno to build on his friend and mentor’s legacy, taking The Tobacconist of Greenwich to new heights and keeping Lacerra’s legacy alive.

“Jimmy used to joke with me that I was a legend in my own mind,” Cafagno fondly recalls. “He gave me enough rope to hang myself, but thankfully all my ideas have worked so far. I’ve been blessed with the right people falling into my lap to show me how to do it. Whenever he spoke, I listened. There is nothing I care more about than that man and his legacy. He gave me a life. There’s no way to express my gratitude. He was a special man.”

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