Meet John Bailey, a Thoroughly Modern Winemaker

As a second-generation vintner and former college athlete, he explains  how he keeps his fitness in check as he joins the family business

Photography by ALANNA HALE


JOHN BAILEY and Knights Bridge winemaker Derek Baljeu taste from barrels in the winery’s caves.


In 2006, John Bailey was just 13 years old when his father and uncle—Jim and Essel Bailey—bought an 83-acre plot of land in Knights Valley, one of Sonoma County’s original five AVAs known for producing stellar cabernet sauvignon. That site would become home to the family and its award-winning Knights Bridge Winery.

“I have three older brothers, and a lot of my fondest memories are [of us] getting in trouble roaming around the vineyard, chasing turkeys,” Bailey recalls. “Growing up, we had family dinner every single night—it’s something my dad stressed—and wine was always on the table. So, even when I was too young to really appreciate it, just seeing the role it played was important.”

While he’s no longer running after wild game on the family property, the now 29-year-old Ivy League-educated finance industry expat returned home at the beginning of 2021, trading in a New York City desk job to focus on East Coast sales distribution for Knights Bridge’s respectable portfolio of limited-production wines. “It’s about meeting with restaurants, distributors and wine buyers, and educating them on what makes our property and the region so special.”

Surprisingly, in college Bailey took only a couple elective classes on wine, but his palate was clearly primed. “One of the alumni came back and taught some of the best wine education courses I’ve ever been part of, going region by region and varietal by varietal,” he says. “At the time, Château Margaux actually had a case study written by Harvard Business School about whether they should release a second wine, and because the reception was held in my dormitory, I got to sit in on that, which was a real treat—definitely not emblematic of your standard introduction to wine.”

In the year leading up to his formally joining the family business, he began working through the Wine & Spirit Education Trust—or WSET—courses, completing Levels 1 through 3. “It’s sort of a different track from the Master Sommelier coursework, for industry professionals who want the knowledge base but don’t want to go that route.”


From top left: Wines are poured regularly in the new facility’s various tasting rooms, which opened to the public last November. Staying active is an essential part of daily life for Bailey.


I got a good cycle in, and then we harvested some of our sauvignon blanc



A competitive athlete—and former Harvard Crimson freestyle swimmer—Bailey takes staying active as seriously as growing the family business. “To me, cycling is like an extension of work,” he says. “We’re right off Highway 128, so I’m out there around 5:30 a.m. and try to make it to Healdsburg and back. Or I’ll take Silverado Trail and head into St. Helena—there are a couple good climbs there too.” After that, he goes to the winery to meet the production team, which includes 27-year-old winemaker Derek Baljeu, with whom Bailey shares a passion for both wine and waves.

“Derek’s brilliant and has an incredible resume, but we really hit it off over surfing,” he says. “When we’re not in the middle of harvest, we typically head out to Bodega Bay—there’s a couple of different breaks out there, like Salmon Creek, which is a favorite.”

With the completion of Knights Bridge’s new winery in July 2021, the second-generation vintner splits his time between responsibilities in the on-site winemaking facility and tasting room—which began welcoming guests that November—and flying back east to meet existing clients and prospects. “This has been a life-long dream for my dad, so to be able to communicate that we’re a small-production family operation and that we’re trying to make artfully crafted wines in this beautiful AVA in Sonoma really excites me.”

One of his favorite wines to tout is the estate’s opulent and lush Fairview sauvignon blanc, a direct-to-consumer wine that isn’t widely distributed. “It’s a beautiful wine, and Fairview was the name of a one-room schoolhouse where my grandmother got her first teaching post—and that really kicked off everything for my entire family,” he notes. “She was an incredible educator for 60 years and made sure all of her four kids went to college—the first in our family’s history.”


From left: Surf’s up for Bailey and Baljeu when harvest is well in hand. With water conservation in mind, a large portion of the family’s vineyards are dry farmed.


At the end of a long day, Bailey can usually be found unwinding in his natural habitat, surrounded by mountains and vineyards.


When we’re not in the middle of harvest, we typically head out to the breaks on Bodega Bay 



Bailey’s activities during the recent harvest kept him in constant motion. “Monday last week I flew in from New York and we hosted a dinner that night with a [local] distributor,” he says. “The next day I drove out to Knights Valley and got a good cycle in that morning, and then we were able to bring in some of the whites. We harvested some of our sauvignon blanc, a little of our chardonnay and just a fraction of our cabernet—harvest is basically between the beginning of September through mid-October, but it changes a bit every year. In general, there’s a lot going on every day, so you just have to go with the flow and help out where you can.”

This past February, the family acquired a neighboring 50-acre vineyard and increased their planted acreage to just over 80. “We’ve been practicing organic for the past four years and should be certified organic within the next year and a half,” says Bailey, who notes that being good stewards of the land has always been a priority for the family. “With the investment my father made in the winery and vineyard, we have a goal to make honest and beautiful world-class wines that represent us and where we are in Sonoma—and we want to carry that 100 years into the future,” he offers humbly. “I really have a lot of gratitude to be able to do what I do.”



Feature image: Cycling across the nearly 133-acre property offers Bailey new perspectives on the fruits of his family’s labor.


This story originally appeared in the Men’s Fall 2022 issue of C Magazine.

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