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The Brand Man Returns

Jonathan Drew grew up on Long Island before he pursued his cigar dreams all the way to Nicaragua. Today, he calls Miami’s modish Wynwood neighborhood home.
Photo/Jeffery Salter
Jonathan Drew grew up on Long Island before he pursued his cigar dreams all the way to Nicaragua. Today, he calls Miami’s modish Wynwood neighborhood home.

Jonathan Drew, a little older and a little wiser, is back as president of Drew Estate

Sixteen square feet.
That was all the space Jonathan Drew had to work with when he opened a cigar kiosk in The Mall at the World Trade Center back in 1995. Little did he know how much that kiosk would alter the course of his life, as he would forgo a career in law and build such popular cigar brands as ACID, Liga Privada, Herrera Esteli and Undercrown.
But on this day, an unseasonably warm February morning in Lower Manhattan, Drew stands beside the manmade waterfalls of the 9/11 Memorial, where the Twin Towers once stood. Wearing whitewashed jeans, a graphic T-shirt and a stark white sport coat, topped with a matching white winter hat and blue-tinted glasses, his outfit would stick out in the typical cigar shop. But on the streets of New York City, he is just another disparate soul in the throng. It's been more than a decade since he's been back in this area, and he fondly remembers the time when he was "the cigar guy" in the North Tower.
"I called my kiosk QC Cigar Company. I told everyone it stood for quality control," he says, "but really it was Queen's Counsel." This was a nod to the fact that, while he was running the kiosk, he was also studying at Brooklyn Law School to become an attorney.
Originally, he had planned to open a cigar shop near home in Brooklyn Heights, but he got a lead that the World Trade Center was looking for vendors to populate its newly rebuilt concourse level. He seized the opportunity and signed a $2,200-a-month lease for the prime retail spot, with the cigar boom in full swing. The kiosk sold brands such as H. Upmann, Macanudo, Flor de Florez, La Gloria Cubana, Fonseca and Davidoff. "Ninety-five percent of my leads as to who to call to buy cigars from came from Cigar Aficionado," he says. "The ads at the bottom would always have a telephone number to call. Back then there were no websites, but everyone had a telephone number."
Drew's phraseology is unique in the cigar industry. At times he sounds more like he's performing a braggadocio rap in a hip-hop song than answering a question or marketing a new product. Hidden underneath the verbal onslaught are the workings of a highly intelligent businessman who is not afraid to loudly share his opinions, even if he sometimes refers to himself in the third person.
"J.D. had an office at 196 Broadway. I had a dolly that I'd stack with cigar boxes and bundles," he says, pantomiming the laborious process with exaggerated movements and a smile. "Then I'd walk down Dey Street, or sometimes past the [St. Paul's Chapel] graveyard. I'd dump it out, right in the middle of the Trade Center, slice the boxes and restock the kiosk."
On Saturdays Drew would boost his income by hawking wares that weren't selling at his parents' Long Island antique shop at a street fair in Manhattan. "On Sundays, I would sleep sometimes for 24 hours. So, my work ethic—that's when it really kicked in."
His hustle paid off as his tiny kiosk did roughly $580,000 in sales in the first year. "Cigars were so hot at the time that I had lines like McDonald's." But Drew wanted his own brand. "The antiques, I knew that wasn't going to be my path forward. The law? I absolutely hated that stuff, but I did it for the cash."
In came Marvin Samel, who had attended the State University of New York at Oneonta with Drew and was working as a mortgage broker at the time. The pair had become fraternity brothers while in school, with Samel graduating a year behind Drew. Samel helped Drew to buy out an early investor in the kiosk, and the pair formed Drew Estate Inc. in 1996. He finished his legal studies that year, choosing to attend his graduation only for five minutes ("I had work to do.") The duo then enlisted La Rosa Cigars, an old-time chinchalle located on Sixth Avenue in Manhattan, to create their first brand: La Vieja Habana. Drew says he named it for the city-center of Old Havana, which in Spanish is Habana Vieja. To better appeal to customers, though, he switched the order of the Spanish words to mimic one of his favorite brands at the time: La Gloria Cubana.
At this point, Drew also became an independent sales representative for Nick Perdomo of Nick's Cigar Co. (now Perdomo Cigars). His territory included 15 states, and he hired a team to help visit cigar shops. He instructed the sales reps to also sell his La Vieja brand. While the strategy boosted La Vieja's reputation, finances were spread thin. "I had all these people working for me; that's why I was losing money," he says.
In the second year, the kiosk did more than $810,000 in sales, but much of that was done wholesale to other cigar shops. "When we added up all of our costs, we were actually losing money by selling wholesale to other shops," Samel told Cigar Aficionado in 2010.
At over 96,000 square feet, La Gran Fabrica Drew Estate is the largest factory in Nicaragua, producing an estimated 170,000 cigars per day, entirely by hand.
At over 96,000 square feet, La Gran Fabrica Drew Estate is the largest factory in Nicaragua, producing an estimated 170,000 cigars per day, entirely by hand.
To keep the La Vieja brand, production was moved to Perdomo's Tabacalera Perdomo factory in Nicaragua. The brand received critical praise, scoring 89 points in a May 1998 Cigar Insider tasting, and sold well. But as it was taking off, Hurricane Mitch hit Central America, and production halted.
"I had a transitional moment—it wasn't even a tipping point," he says, delving into his signature circular reasoning. "Because when you think of a tipping point, you kind of think of a line in the sand. But that line in the sand is very blurry, brotha. It's like falling in love with a woman. It's not like you fall in love with a woman and say, ‘That's it!' Falling in love with being a manufacturer of something, back when I got into it, in a world where there were no gringo guys making cigars. It was really mind warped."
Determined, he borrowed $100,000 and headed to Nicaragua to learn as much as possible about cigar production.
Jonathan Drew was born Jonathan Sann on July 5, 1969 in Babylon, Long Island, New York. Growing up in Suffolk County, he went to school in Southampton, while his parents ran their antique store. Throughout his childhood, the household was filled with aged wares.
"It was packed to the rafters," he says. "[My parents] kept all their antiques in banana boxes. Chiquita banana boxes, stacked up to the ceiling. You'd have a line from the kitchen to the living room; kitchen to the stairway. So, there was nowhere to move in my house. I hated those banana boxes."
His parents' collection of antiques may have hindered his youthful mobility, but he believes they taught him to not only appreciate history, but to understand "the moment in time when something was created and why it was created and what was the lineage behind the product."
A self-described "thrasher kid," Drew was a fan of heavy metal music at a time when it began to converge with hip-hop. While the lyrics, the bravado, the feuds and the rawness of hip-hop spoke to him, Drew also had great admiration for the producers behind the artists and how they distributed and cross-promoted musicians.
After high school, Drew headed to SUNY Oneonta as a political science major with a minor in business. In the final semester of his senior year, he landed an internship working under then New York Sen. Alfonse D'Amato in Washington, D.C. "[His staff] used to call me ‘Baby Alfonse' because they said I looked a lot like him," recalls Drew.
One night, as he was waiting for the Senator outside a function, D'Amato's driver reached into the politician's stash of cigars. He handed Drew his first cigar, a Partagás Serie D No. 4, and the two lit up. It was love at first puff.
"The first cigar was beautiful," says Drew. "That's the thing: If you start off with a good stick that isn't overpowering, doesn't knock you on your ass—you know, turn you off—the chances of you becoming a cigar enjoyer is higher."
Drew envisioned himself entering politics and enrolled in law school. He worked on D'Amato's 1992 reelection campaign, and as a legal assistant from 10:30 at night to 7:30 in the morning, three or four nights a week. "It was going to be a career job. I got $15 an hour and $18 a night for dinner," he says. "I opened the kiosk to be able to pay for law school, which is expensive. Plus, I needed cash in hand, because I always liked the ladies and I liked to go out and I liked to have fly gear." He winks.
And, of course, he continued to smoke cigars, everything from H. Upmann Lonsdales to Cuban Davidoffs. But he wasn't just a casual smoker, but a lover of the leaf who had a deep interest in learning about the stories behind the cigars.
"Brands excite me. Brands get into me. I would walk into the stores and pepper the owner or the manager or whoever was in the store, with so many questions about the history of the brand," Drew says. "I was really bombarding them with questions that were not so much about how does the cigar taste. I was more interested in the who and the why. I valued [a brand owner's] lineage. I valued their journey. I valued their results."
At this time another medium also caught his eye: graffiti. Drew would puff a cigar and walk through Manhattan's SoHo neighborhood, craning his neck to see the intricate tags, murals and stencils of various street artists. Some of the art resonated deep with Drew. "There's a rawness to graffiti that I need," he says.
Today, Estelí, Nicaragua is a thriving municipality, teeming with dozens of cigar factories surrounded by tobacco fields. In 1998, when Drew arrived, it was a vastly different landscape, with only a few cigar companies that called it home, almost all owned by expatriate Cubans. "I was the only gringo out in Estelí," Drew says, proudly. "Go out to Estelí today, and you bump into this guy or this gringo guy. Back then, there was nobody."
Drew proved himself through hard work and dedication, at times even sleeping on a mattress on the floor of a room in the Tabacalera Perdomo factory as he worked to develop a cigar brand that combined his affinity for hip-hop and street art: ACID. He had conceived the brand with Samel and friend Scott "Acid" Chester, a New York-based designer.
ACID cigars are infused with essential oils, herbs and botanicals, but unlike a typical flavored cigar, they are handmade and use long filler tobaccos. The various lines are adorned with brightly colored bands reminiscent of graffiti. When ACID debuted at the 1999 cigar trade show, it was an immediate success. Many millions of ACID cigars have been sold since, and it is fair to credit the brand with making the infused cigar market as large as it is today.
"At first I didn't think it would sell," says Jeff Borysiewicz, who owns four cigar retail stores in Florida, including the enormous Corona Cigar Co. in Orlando. "I just didn't know about the name. But it sells phenomenal and is popular with all kinds of smokers, young guys to middle-aged men."
In 2005, Drew and his company decided it was time to dive into the traditional cigar market. "We were known as the ACID guys, or the infused guys. We wanted to be the Drew Estate cigar company. People wondered why we didn't just make ACID. Less inventory, less problems," he says. "But it wasn't fun just to make that. I have a lot of things I got to make. If you're an artist, you're not doing only one show. You want to get to the next thing."
The following year the company debuted Château Real, an eight-size line that averaged 87 points in a May Cigar Insider vertical tasting. However, it was not the mega-hit Drew had hoped for, and he refers to it as "a total failure."
Drew believes Château is a good cigar (the company still makes it), but that it was too safe a bet when it debuted. It didn't possess any swagger or style, two attributes that Drew sees that help define part of the core values of Drew Estate. He learned from the experience.
Housed within the La Gran Fabrica Drew Estate is Subculture Studios, headed by Jessi Flores (center). The studio employs dozens of local graffiti artists to design cigar packaging, accessories and point-of-sale concepts, and even tag the occassional wall.
Housed within the La Gran Fabrica Drew Estate is Subculture Studios, headed by Jessi Flores (center). The studio employs dozens of local graffiti artists to design cigar packaging, accessories and point-of-sale concepts, and even tag the occassional wall.
"You could make the best tasting cigar on the planet, but if your aesthetics aren't right—packaging, graphics, the boxes and the place that it takes you to, if that ain't right, no matter how good the cigar, it's just probably not going to be a super successful brand. The trifecta is when you make a cigar that tastes really great, package it and position it well, and you make the cigar a winner, meaning great construction."
Drew and his team hit a trifecta with the brand they released in 2007: Liga Privada No. 9. While many companies were touting puros, Liga was a four-country blend that included Brazilian Mata Fina (rarely used at the time) wrapped in expensive, tantalizingly dark, broadleaf tobacco grown in Connecticut. It debuted in one size, a 6-inch-by-52-ring-gauge parejo. The bands appeared to be handwritten and resembled labels found in distillation plants or tasting laboratories. The brand quickly became a cult hit. 
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