How Jackson Cannon Helped Build (and Rebuild) Boston’s Cocktail Culture

The Boston cocktail scene has suffered some serious blows over the past few years. Brother Cleve, the musician, DJ, and mixologist who was regarded as the godfather of the Boston cocktail revival, died suddenly in September 2022. In January of this year, Drink, a pioneering local bar, shuttered for good.

For a long while, it looked like Eastern Standard—the stylish and influential high-volume bar and restaurant near Fenway Park that opened in 2005—might also be among those casualties. It closed in March 2020 when the Covid pandemic hit. Fairly soon, owing to a lengthy landlord dispute, it became clear it wasn’t coming back, at least not to its original location.

But last fall, three and a half years later, Eastern Standard unexpectedly reopened in a larger space just a short walk fromits former address. And back with it was another name long associated with the Boston cocktail world: Jackson Cannon.

[It] was surprising that Cannon—a bar world veteran with decades behind the stick and very little left to prove—would return to the day-in-and-day-out grind of running a bar.

Given that many hospitality professionals left the industry during the pandemic, it was surprising that Cannon—a bar world veteran with decades behind the stick and very little left to prove—would return to the day-in-and-day-out grind of running a bar. But to Cannon, the question was never in doubt. “I considered what options were there for me in the immediate closure,” Cannon says. His conclusion: “I crave the hospitality part of it.”

While Cannon and Garrett Harker, owner of Eastern Standard, stayed in touch during the pandemic, Harker never assumed that the two “would get the band back together,” as he puts it. “To me, I romantically chalk it up to, he’s still got the rock star music side. He still wants to perform. The curtain goes up every night.

“I think of some of the easy off-ramps, elegant ways to age in this business,” Harker continues. “This is probably not one of them.”

The band metaphor is apt, since Cannon’s pre-bartender career was as a musician. Cannon keeps that side of his life private, and Harker has only heard him play once, when a band scheduled to perform at Eastern Standard on Valentine’s Day in 2007 canceled due to a blizzard, and Cannon and some pals stepped in. His staff stared in disbelief. “Managing the team got a little easier after that,” says Cannon.

The Hawthorne, a cocktail bar that was linked to Eastern Standard, and a partnership between Harker and Cannon, was not resurrected. Instead, nestled in the back of the new Eastern Standard space at the end of a long corridor is the new Equal Measure. Like The Hawthorne, its raison d’être is cocktails of a very high craft.

“Equal Measure is a new brand,” explains Cannon. “People think of it as Hawthorne 2.0 who were regulars there—a place where the cocktail is a dominant experience, food playing a supporting role,” where ingredients can be weirder and spirits can be spotlighted. But, Cannon cautions, “It’s not a one-to-one.”

“Equal Measure has morphed into its own thing,” says Eliza Hoar, the bar’s head bartender. “It’s a bar where we want to celebrate ingredients that you don’t normally find inside a glass.”

Hoar—who bartended in San Diego for many years—moved clear across the country to take the post at Equal Measure. Cannon landed his new hire during a 3 a.m. meeting at Erin Rose, the beloved New Orleans dive, in the thick of the 2023 Tales of the Cocktail convention. “We got into a very long conversation that, by the end of it, he said, ‘Would you want to come and check out Boston?'” recalls Hoar.

Cannon made the offer solely on instinct. “When Liza tells this story, she says, ‘He never saw me touch a tin,'” says Cannon.

Creating a new bar is a challenge. Re-creating a famous one is arguably even more difficult. “Our restaurant closing represented something in the community that felt like we were really losing something,” says Cannon. He and Harker knew that reanimating that restaurant and the bar’s soul in a completely different space would be a tricky proposition.

“We were a new restaurant,” explains Cannon. “We were going to have new restaurant issues. And, we’re sitting on this legacy brand, a legacy built over 15 years.” He knew he couldn’t open with the small wine and cocktail lists he did in 2005; returning regulars would expect more. At the same time, he also couldn’t hit the ground running, with a brand-new staff, as if it were still 2020. “I just took everything down to as simple a form as I could. And then we just listened to the guests,” he says. “People would come in and say, ‘I used to have this cocktail in 2014. Can you make it?’ And I’d just turn that into that week’s bar muse, so we could all learn it together again.”

In some ways, Eastern Standard had shed the bratty persona it had in 2005 and matured alongside its operators.

In some ways, Eastern Standard had shed the bratty persona it had in 2005 and matured alongside its operators. “I would say, spiritually, the old Eastern Standard, we had a chip on our shoulder,” says Harker. “The bar certainly had a lot of swagger. We were definitely a little antagonistic. We got a kick out of withholding the spirits people wanted to drink. There was no Bud Lite. There was no Absolut and Grey Goose.” Now, Harker’s attitude is, “Just relax. Anybody wants a High Noon? Fine.”

“You know how it is,” says Cannon. “We’re trying to make one regular at a time.”

Cannon was on the ground floor when the Boston cocktail revival got underway in the late 1990s. At one point he, Brother Cleve, and Misty Kalkofen, another Boston cocktail luminary, lived in the same house. Together, they formed the Jack Rose Society, a loose collective of drink geeks who periodically taste-tested old cocktail recipes until they got them right. One of these, a Jack Rose mixed with real grenadine made from scratch, helped define the early direction at Eastern Standard.

Cannon learned quickly during the pandemic how much he missed hospitality work. He pivoted to online bartending as a source of income when he was asked if he’d do a private cocktail class for Linda and John Henry, the owners of the Boston Red Sox and Boston Globe, and their friends. It went so well, the Henrys asked for a second class. The Monday mixology appointments lasted from May 2020 to June 2021. This, in turn, led to a public version of the gig at Boston.com, called the “Boston.com Cocktail Club.” He did nearly 100 half-hour shows.

“We were so impressed with Jackson’s knowledge and passion,” says Linda Henry, “that once we were gathering in person and didn’t need to Zoom anymore, we asked Jackson to continue a version of the cocktail club on Boston.com as a free cocktail class for the city.” Cannon’s virtual bar made him understand how much he missed working a real bar. “I’d come to realize after a year of that that I had regulars during that time,” says Cannon.

Cannon approaches many aspects of his job in old-school ways that are not necessarily the norm in cocktail circles anymore. He attended his first Tales of the Cocktail in 2006 and has gone every year since, insisting the time be carved out from his Boston work schedule. “It is the week that fills my cup,” he says. “I learn so much.” And he brings booze industry professionals into his bar as often as he can for the edification of his staff. In July, for example, writer and ice expert Camper English was invited to speak. “I always believed that craft and knowledge of historical craft, that was a weapon to be deployed to raise the hospitality in the bar environment,” says Cannon. “I still believe it, I still see it.”

All of this, along with his many years of service, would seem enough to bestow upon Cannon the title of mentor. But Cannon bristles at the suggestion. “I don’t sit back and think of myself as a mentor,” he says. “I come to work inspired to teach and learn with my crew every day. It does not mean anything to me if it’s not collaborating. I can’t do it any other way.”

“[Cannon’s] role as mentor seems paramount to Boston’s continued relevance in the cocktail scene.”—John Gersten

Others, however, are happy to step up and give him the props he won’t give himself. “Jackson has continued to provide an opportunity for his team to provide a world-class hospitality experience,” says John Gersten, one of the few Boston cocktail vets with as many stripes on his sleeve as Cannon. “As our industry evolves and responds to the challenges of the post-Covid workplace, his role as mentor seems paramount to Boston’s continued relevance in the cocktail scene.”

Cannon remains such an enthusiastic member of the cocktail community that, nearly 20 years after he started seeing his name in the papers, he gets excited about this article. “I’ve been around as long as Imbibe has been in the business,” he says. “To me, there’s still a little bit of wonder about all that. People are like, ‘So, what space are you in in the industry?’ I’m just an excited nerd who likes to take care of people.”