The roughly $500 he made on his first day selling cigars from a cart — keeping fans near the 5’ x 4’ humidor to keep it cool and getting some help with the setup from his mom and dad — put him on his way toward paying the cart’s monthly rent, which he says was about $3,000. It was also the beginning of the formation of the business’s identity, which is informed by not only the struggle of its leaders to keep it afloat and innovate, but also by the gritty hip hop culture in each of the places it’s called home. That identity developed as the business branched off into different aspects of the cigar trade — namely humidors, as well as cigar sales and distribution for other established brands.
“That was way back in the day. I had the red and black lumberjack jacket with the hat to match,” Jonathan said, alluding to the lyrics of Juicy. “It was good times. I was on J Street in Manhattan, and right next to me was Jay Z and Roc-A-Fella Records. They were nobody. In that time period, you had Biggie blowing up in New York, you had Puff Daddy, hip hop was in a transitional period.
And that’s really important to the earliest days of Drew Estate. Because one of the things that always distinguished us from everybody else is that we weren’t a cigar company. We knew we weren’t a cigar company from minute one.”
Rather than a cigar company, Drew Estate sees itself as dealing in lifestyle and experiences. It’s an approach that separated them from their competition in the earliest days and continues to do so today. In the earliest days, when Jonathan was running things from Dumbo, Brooklyn, just beyond the end of the Manhattan Bridge that’s a hallmark of Drew Estate branding, that lifestyle brand approach began to reflect the company’s New York City roots. In fact, a year after the cart business launched, the company’s first brand, La Vieja Habana, was rolled in New York City by a small company called La Rosa Cigars. And then it wasn’t.
“The guy who made those cigars, Antonio Al- manzar, got decapitated,” said Jonathan. “They slid in the rain under an 18-wheeler in his car and his head got taken off.” The freak accident created a need to find a new manufacturer for La Vieja Habana. That’s when Jonathan hooked up with Nick Perdomo.
“Nick was supposed to make them in Miami, but his dad had moved to Estelí,” said Jonathan. “So I was going out to Nicaragua every time he did, eight or nine times a year in ‘96 and ‘97.”
At the time, Jonathan was also considering having La Vieja Habana made by other companies. For instance, he said he came close to going with Ernesto Pérez Carrillo, who was making his cigars in the Dominican Republic. Instead, frequent trips to Estelí brought Drew Estate closer and closer to the next chapter in its story, and Jonathan Drew closer to his next home.
“It was very creepy. You would go to Nicaragua and everything was riddled with bullet holes,” Jonathan said. “People were not proud to be making cigars in Nicaragua. It wasn’t like it is now where ‘Nicaragua’ is written all over everything.”
It’s hard enough living under the conditions that seem to come standard in any Central American economic or political system. At the time Jonathan started getting to know the country, Nica- ragua was also reeling from the Contras and the Sandinista National Liberation Front. Goods and services were in scarce supply, and getting a business off the ground — especially as a gringo with more of a cultural gap to bridge than many of the Cuban families whose companies had put down roots (think Padrón, Perdomo, etc.) — wasn’t easy.
“No place in Central America is as loving of people as Nicaragua. Nowhere at all in Central or South America is as safe as Nicaragua. Nowhere,” said Jonathan. “Including Mexico, Panama, Costa Rica, nothing. But that’s not what it was back then. It was rougher. Women couldn’t get makeup. Forget cell phones. The roads were bad. Medical equipment and needs were really bad. Couldn’t get cars either. Getting a telephone line took a year. I couldn’t get a bank account open for almost two years.”
At first, Jonathan made the transition to Nicaragua by living in the Perdomo factory. That was about the time that he crossed paths with Jeff Borysiewicz, his longtime friend and owner of the Orlando-based Corona Cigar Company.
“I remember when my supplier of Lars Tetens cigars didn’t sell them anymore. I was all pissed off because the rumor was some young lawyer dude from New York named Jonathan Drew was the one doing the distribution. I immediately didn’t like him even though I’d never met him,” Jeff said.