Drent’s office is a warm room, filled with wooden furniture, man-sized humidors, vintage signage and the faintly acrid aroma of aging cigars mixed with the smell of roasting coffee. He presents me with a Paris-worthy latte he’s just made, its meringue-thick foam scored by delicate lines of espresso. “Try it without sugar first,” he says. “I always tell people that.” When I say it’s the best latte by far I’ve had in Hawai‘i, Drent smiles with satisfaction but not surprise: He’s been growing coffee since 2001 through his other company, dramatic success and agonizing failure Blair Estate Coffee (Blair being his middle name). I’ve caught up with him, in fact, on the day before the busiest day of his year; while the tobacco’s being picked up the road, the coffee will be simultaneously harvested here on the property where he lives with his wife, two kids, two lazy cats and a brood of plump laying hens.

Drent’s voluble, affably caffeinated and he talks fast when he gets going about his passions, whether coffee, cigars, baseball or writing. When he came to Hawai‘i in 1991, he had no intention of farming; he wanted to be a journalist. He’d been grinding out ad copy in Los Angeles long enough to realize he hated it, so he put his beat-up Toyota on a barge and headed for the tropics. He wound up living on a coffee farm above Captain Cook, where he “had this idea to start a publication, really cheap,” he says. “I had no money, no computer. I was going to do the whole thing by hand and photocopy it.” He scraped the $4,000 in startup cash together by taking $10 photos of tourists in Kailua-Kona in front of a coffee plantation scene he created with props he’d borrowed from the farm. The first issue of Coffee Times, which covered the Kona coffee industry, rolled off the photocopier in 1993. It was enough of a success that Drent could buy his own press but not successful enough that he could hire help. “I wrote it, shot it, delivered it, did the billing. I printed it in an old macadamia nut shed in Holualoa … all night long, the whole shed shaking,” he says. “It was horrible.”

Eventually the one-man operation took its toll, so after what he affectionately calls his “nervous breakdown” in 1995, he started roasting and selling mail-order coffee. This was before Kona had made the big leagues (“$11.95 a pound for 100 percent Kona Peaberry,” he recalls. “Can you believe that?”), but the writing was on the wall as new money moved in and the region’s reputation started to build. “I thought, ‘I’m going to get squashed with all these dot-com guys coming over. I just can’t afford land.’” When he picked beans from a wild coffee plant on a visit to Kaua‘i, Drent’s life changed. “It was just the most amazing coffee I’d ever had. It was euphoric, amazing.” So in 1998 he packed up his roaster, headed for the Garden Isle and with his parents’ help bought three and a half acres in Kapa‘a. By 2001 Drent was a successful farmer, roaster and purveyor of Kaua‘i coffee.

Three years later another fateful encounter with a wild plant—a kelly green weed growing in a neighbor’s garden— would again alter Drent’s life trajectory. “I asked him, ‘What the heck is that?’ ‘It’s tobacco,’ he said. ‘Tobacco, really! Can I have some seeds?’” The neighbor broke off a pod, and the rest, says Drent, is history—a tortuous one. If Drent had known anything about tobacco, he says, he probably wouldn’t have touched the stuff. The first cigars he made from that wild tobacco, a descendant of a Sumatran variety growing throughout the Islands, were “terrible. Horrible. Brutal.” But tobacco, as is well known, is highly addicting, and Drent was hooked. He bought some Connecticut seed, which yields a light, mellow tobacco (a “forgiving cigar,” as he puts it), and hit the books, scouring the Kaua‘i Community College library and the Internet for all the information on tobacco cultivation he could find. In 2004 he produced his first commercial crop, which yielded about a thousand cigars. They weren’t all that good, Drent says, but he packaged them in homemade boxes and put them in a couple of local gift shops anyway. They sold out— fast. “I was like, ‘Wow, there’s that many people liking cigars out there?’ That’s when the lights went on.” But to take things to the next level, to produce a quality cigar, Drent had to get serious. First he had to grow stronger tobacco. He procured some Habana2000, a Cuban-seed variety with big leaves and spicy flavor, from the Oliva family, one of the biggest names in cigar making. The stronger the tobacco, though, the more carefully it needs to be processed; screw it up and you get “a bonfire in your mouth,” says Drent. So he asked the Olivas to help him find a “legitimate, bona fide expert” to handle his tobacco. They connected him with Victor Calvo, a master ligador (blender) and cigar maker in Estelí, Nicaragua. Estelí, a town in the hill country near the Honduran border, was a haven for cigar makers fleeing Cuba’s communist revolution in 1959; they turned it into one of the most important cigar-making centers in Latin America. Drent followed his 2006 crop to Estelí, where Calvo initiated him into the secretive world of premium cigar making.

In 2009 Drent tried fermenting the harvest in Hawai‘i based on what he’d learned in Estelí with the eventual aim of bringing the entire process, from seed to cigar, to Kaua‘i. It was a disaster: The piles overheated, which led to molding. “There’s a big difference between fermenting and composting,” Drent laughs, still a little ruefully. “Three thousand pounds of tobacco and $60,000 in labor, all ruined.” Lesson learned, Drent’s been sending his tobacco to Estelí since. Last year he sold about 90,000 cigars through ABC Stores, Whalers Village and Foodland among dozens of smaller specialty shops and a handful of Mainland stores; he’s currently developing an exclusive line for local craft shop Martin & MacArthur.

The irony in all this is that Drent’s not a huge cigar guy himself. He’ll indulge in one or two a week, tops. “I always loved the smell of a good cigar, you know, outside of Fenway Park growing up and smelling those Dominicans down there, but I never really got into the pastime of smoking them.” For him the satisfaction lies in having done something nobody else has, something unexpected and maybe a little nuts. “Who’d ever have imagined there’s a guy in Hawai‘i growing tobacco and making cigars?” he shrugs.