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The Tommy Bahama Boys

Tommy Bahama's three creators rhapsodize about making their fantasy a successful reality

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"I don't think cigars are on the top of any of our wives' wish lists," says Emfield, with a grin, "so cigars are banished to the outdoors at our homes or to some other dark, dank place where our wives wouldn't go anyway. When I do smoke, I really like a Partagas Serie D No. 4 or maybe a Montecristo No. 2 for late afternoon or early evening. I prefer to smoke before dinner. I don't drink, but I like to sit down with my friends who have cocktails and let an hour pass, and in place of a Martini I smoke a cigar. And, of course, in Florida and here [in Naples] it's all about timing and the sun setting into the Gulf of Mexico."
Margolis concurs with the importance of sunset timing, but with slightly different parameters. "Unlike Bob, I do drink alcohol," Margolis says with a laugh. "I think a cigar goes really well with a Martini. I also like to smoke before dinner—sunset's a great time—but I prefer a Hoyo de Monterrey. I also don't mind an afternoon smoke sometimes, and I think Davidoff makes a good afternoon cigar. For me, a cigar is an unwind's similar to drinking [wine] and the enjoyment of wine in that it has a lot of the same tactile features of taste, smell."
For Dalla Gasperina, the aspiring winemaker with Cabernet, Sauvignon Blanc and Merlot grapes growing in his vineyard, an occasional cigar for celebratory purposes with "the boys" works just fine, as does pairing that cigar with some nice wine. "We're pretty fortunate in that we usually have access to a nice repertoire of cigars...the better Dominican or Cuban cigars, for instance. I like the Partagas Serie D No. 4 too. It's a nice way to recap a day's events when we're together, maybe in Las Vegas or in Hong Kong, and it's just wives! They hate the way we smell [after smoking], and when we smoke and go home, you know, we have to leave our clothes in the garage!"
Like anything else, cigar smoking is about lifestyle choices, and no one seems to know more about lifestyle choices than our man Tommy. Along with Dalla Gasperina's inspired apparel designs, what Tommy Bahama as a company seems to do best is define a particular lifestyle—casual but successful, affluent but low-key—that its customers have either already achieved in life, or aspire to. And if that means, in addition to clothing, outfitting a home with Tommy Bahama furnishings and proffering a bottle of Tommy Bahama Golden Sun Rum at the bar, well, the company has made its mark showcasing that lifestyle. Not to mention some very profitable licensing.
"Licensing has been extremely lucrative for us," admits Margolis, "but if Tommy wouldn't wear it or sit on it or have it on his boat or in his home, then Tommy's name doesn't go on it. It's that simple."
Besides the myriad product lines, Tommy's name is on over 60 retail stores around the country. The men hope to expand into international locations next, with plans to create more compounds similar to their original one in Naples.
That the 20,000-square-foot compound in Naples continues to be their most successful venue makes sense. Naples' sun-drenched climate and demographic are a perfect match to the clothing line; locals and tourists alike seem perfectly willing to wait an hour to be seated at the café, and Margolis and Emfield are, for the most part, considered hometown boys, even if they only reside there part-time.
Then again, Tommy Bahama has proven to be a good neighbor, sponsoring and building an impressive garden within the campus of the local NCH Hospital and NCH Regional Cancer Institute. Opened to the public last fall, the Garden of Hope and Courage was the dream of Bob Emfield's first wife, Jan, who died of breast cancer in 1994.
To raise money for the garden, Tommy Bahama's employees held fund-raisers, the company donated proceeds from specific promotions and, together with individual donations, the company raised more than $3 million to make the Garden of Hope and Courage a reality.
And it's a physically beautiful reality. Emfield chose the park as the setting for this interview and, with its small lake and lush landscaping, the park is a tranquil respite for patients at the adjacent hospital and a popular meditation spot for locals.
The company is equally committed to the other communities where it has stores, raising millions each year through golf tournaments and similar events that benefit organizations as diverse as the University of Washington Breast Care Research Center, the Muhammad Ali Parkinson's Research Center, the Elizabeth Glazer Pediatric Aids Foundation and the Children's Cancer Research Fund. Explains Dalla Gasperina, "For every company that has the good fortune to succeed to any degree, there is a responsibility that goes beyond your own little world. To contribute through our success to make people's lives better is a duty and, equally, a pleasure."
So, what's next for the three men and Tommy? The three men offer three different answers, but none expounds any further than his own plans for that afternoon: Margolis is headed to a tennis game, Emfield has plans for a barbecue and Dalla Gasperina is off to a business meeting.
As for Tommy, well, there are a few high-end products that he might like to see added to his branded collection—golf clubs, maybe, or the right yacht or automobile—but what would really rock Tommy Bahama's boat is a resort. A really, really, high-end resort.
"We've been approached," Margolis admits, "but it hasn't been the right deal, the right resort concept. I think a Tommy Bahama resort is a natural extension of what we've done and what we're doing. We've already broken the mold with successful, profitable restaurants and we're perfectly situated for the next step, which would be a beachfront resort or golf resort. Tommy Bahama is known for its clothes, yes, but we're really about an entire lifestyle, and what better way to advertise that than at a resort that offers all the opportunities that Tommy would take advantage of?"
Ah, yes, the "What would Tommy want?" litmus test.
When asked if they ever worry about sounding a little like they're talking about an imaginary playmate, the men laugh.
"No," says Emfield. "Tommy may be fictional but he's also very real. It's about lifestyle. There's a little bit in all of us that wants to be Tommy and a little bit of Tommy already in each of us. Be honest, given a choice, wouldn't you rather be on a beach right now?"
Betsy Model is a frequent contributor to Cigar Aficionado.
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