Episode 110: Jackson Cannon

This episode is sponsored by Tito’s Handmade Vodka.

Boston has long been a beacon of cocktail culture in America, and Jackson Cannon is a big reason behind that. For this episode, we talk with the longtime Boston bartender about the evolution of the city’s cocktail scene over the past couple of decades, and about the re-opening of Eastern Standard, one of the city’s landmark establishments.

Radio Imbibe is the audio home of Imbibe magazine. In each episode, we dive into liquid culture, exploring the people, places, and flavors of the drinkscape through conversations about cocktails, coffee, beer, spirits, and wine. Keep up with us on Instagram, Threads, and Facebook. And if you’re not already a subscriber, we’d love to have you join us—click here to subscribe.

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Paul Clarke 

Hey, everybody. Welcome back to Radio Imbibe from Imbibe magazine. I’m Paul Clarke, Imbibe’s editor in chief. 

And over the course of the almost two decades that we’ve been putting together Imbibe, we’ve always aimed to bring you word of some of the newest bars and bartenders and cocktails that are out there to discover. At the same time, it’s always been our aim to put those bars and bartenders and cocktails into the proper context so we can all better understand the brilliant dynamics we find in today’s bar world so you can fathom how we got to this point. 

For this episode, we want to put the past and present together. Boston bartender Jackson Cannon helped establish the modern cocktail movement in New England and nationwide while building the program at Eastern Standard and working alongside a small army of bartenders from all across the country over the past couple of decades. But Jackson’s story isn’t only rooted in the past.

Following the permanent closure of Eastern Standard during the COVID pandemic, along with its sibling bar, the Hawthorne, Jackson has helped the Boston hospitality world put itself back together by working to reopen Eastern Standard in a totally new location, as well as open another companion bar, Equal Measure. Robert Simonson shared Jackson Cannon’s story in our November/December issue. And for this episode of the podcast, we wanted to give Jackson the opportunity to tell his own story and go a little deeper into the dynamics of the Boston cocktail scene as it’s evolved over the years. 

And a quick note before we get started, fa la la la la into the season with our sponsor, Tito’s Handmade Vodka. From festive libations to cozy cocktails, it’s the most wonderful time of the year to toast with your favorite holiday spirit. Distilled & Bottled by Fifth Generation, Inc., Austin, Texas. 40 percent alcohol-by-volume. Distilled from corn. Copyright 2025. Crafted to be savored responsibly.

Paul Clarke

Jackson, welcome to Radio Imbibe. 

Jackson Cannon 

Really glad to be here, Paul. 

Paul Clarke 

Thank you for doing this and for being back on the podcast. It’s always wonderful to talk to you, and now this is one of the things we do. And I also wanted to have you on because we have a brand-new issue of Imbibe out now for November and December, and for that issue, you spoke with Robert Simonson for a profile of you. And the thing is, when we were talking about you in this context of Imbibe and cocktails and all that sort of thing, we’re also in large part talking about the modern state of Boston cocktails and Boston cocktail bars from which your story is inseparable. So let’s go back a little bit, if we could. When did you first get involved in Boston and Boston area bars and cocktail bars? And what did that look like at the time? 

Jackson Cannon

So I came to Boston to go to music school and basically have left many times, but never permanently. You know, it’s not the place that I’m from, even though I’ve been here many more years than I was anywhere else. And it’s an interesting city in that regard. Like if you’re not from here, you don’t become from here, like some other places where that happens a little faster, maybe because it’s such an old city. But I certainly am of the bar and cocktail scene. And I first really sort of got interested in cocktails through that, through being in bars, through playing music in my twenties.

You know, like a lot of people, right, you’re looking for a little bit better cup of coffee and then you may at the liquor store wonder what the difference between the Chianti Reserva and the regular one that’s $2 less is, and that was always me. I was curious about that sort of thing. You know, I think I bought a cheese primer and we sort of didn’t know that I was headed down a road of just wanting to know more about it now. 

Drinking in my family was a positive thing. And there were my, I come from storytellers. My father and brother are award-winning presidential historians and journalists. And alcohol was socially enjoyed, but often like with a little bit of story behind it. So it was kind of logical as I was in my drinking years and kind of awakening to food and drink and social activity that I would be kind of drawn to it. And I made this joke since, but it really is true. I found a way to spend more time in bars than just showing up with gear, playing for a couple of hours and leaving.

And it was bars when I played music that were always like this real kind of turn on to me. I just felt natural there. I always, these were always my people, all kinds of bars. That’s really how it happened for me that I was starting to do it. And I had the just really good fortune of being near both Brother Cleve and Misty Kalkofen, his protege at a time where it was sort of like I was still playing. Misty was working the door and the floor. Cleve was a musician and deejay.

But the first time that he came back from working in Mexico and turned to us and said, Hey, can I show you the tequila ritual that I learned down there? It was a like a good bottle and like salt and fruit and a little liquid refresher for behind the sips. Sangrita, we now call it. Right. And, you know, I was just sort of like, hooked in that way. You know, we would after gigs, we would try to figure out what do we have that we can make a cocktail with, like stay up late into the night being like, What’s this Rob Roy all about? You know, like. 

Paul Clarke 

Right. And that was one thing. You know, Robert mentioned this in the piece. And early on, you crossed paths with folks like Misty and Cleve who were wound up on this similar kind of journey as you just looking for the more interesting the the story behind it. A little bit more detail, a little bit more craft. And I think that was when I first came across your name before I ever met you in person was through the story of the Jack Rose Society and then the things that you had been doing. Take us back. You know, fill this in a little bit more on the kinds of things that you were doing on those early days of the cocktail renaissance there in Boston and how all of you kind of came together in that way. 

Jackson Cannon

Right. Well, all of these words renaissance, you know, Jack Rose Society. I mean, they really dignify what couldn’t have been a looser, you know, approach. We were drinking. We were partying. 

Paul Clarke

Yeah. 

Jackson Cannon

Having a good time. We were taking care of one another, you know, But we we were we were interested in it, you know, what was behind it, who had done it before, you know, like and not everybody was interested in that part of it. And those of us that were we found each other. So, you know, there’s a through line through there.

I think that you can relate to a lot of writers or musicians like adopt kitsch from different periods because of that thread, that connection to other elements of culture because none of this happens, not music, not food, not drink, none of it happens in a vacuum, right? It all happens as this thing we do together in moments in time. And so, you know, that was that was really what it was all about. And there just, you know, if you wanted a cocktail book, you had to go to every vintage store.

It’s hard to take your mind back to. I mean, Cleve got me this address of somebody in Ann Arbor, Michigan. You would write to them or call them if they answered the phone, and they would say, Oh, how much money do you want to spend? And you would tell them you would send them a check and they would just send you a bunch of vintage books. So you know that that part of it we read from them together. We would share those those experiences.

And this was happening everywhere, right? This is happening in in Seattle, you know, with the likes of Murray and, you know, reading and and knowing the stuff and teaching it and being connected to other people who are doing it. And it just to over time, you know, grew and grew and grew. But we didn’t know it was headed for anything other than, you know, a hangover some of those nights, you know, so. 

Paul Clarke

Yeah. Yeah, exactly. You know, it’s impossible to talk about the modern era of cocktails, period, and Boston cocktails specifically without talking about Eastern Standard. And it’s now in its second iteration. And we’ll get to that in a moment. But looking back at the original location, the original idea going into Eastern Standard and the original state of the place, what were you aiming to do and how did it wind up functioning within that broader range of what was going on in the rest of the cocktail world? 

Jackson Cannon

Well, it’s an interesting set of circumstances and it’s really before quote, cocktails broke. It’s Garrett Harker, the proprietor, wanting to follow through on some things that he’d begun when he was managing Number Nine Park. You know, he’d met Dale [DeGroff], heard him at a lecture actually talk about and it seems quaint now, but remember this your kitchen is using fresh ingredients. Why are you using powdered mix at the bar? Number Nine Park, our greatest restaurant of that era was doing that. And he heard that and had an epiphany as an operator who really doesn’t have a lot of beverage experience beyond overseeing the people who oversee it. And they had a great bar. They’re small and classic and welcoming, and they began to tie into the kitchen that way.

So when he was going on his own to do Eastern Standard, he thought, well, what’s more, architecturally proof of the fact that we haven’t been thinking about the bar for decades, that it’s this tiny little area in the back at cool restaurants. Let’s put it right down the middle of the restaurant, big brasserie style. And that was that was very new for Boston, new in a lot of ways for the for the country. There’s a lot more of that that came after that. But that’s sort of like kind of the one element to remember the owner had this idea based on what we all believe, to celebrate the bar in the front of house and keep it connected to the kitchen the way they did it.

And for my part, I interviewed a little long in the tooth for a job like that, you know, I’m not going to say. But even then I felt like, you know, most bar managers and that was my my opening role. There were bit younger than me, but I was also new to the professional part of the business, right? So I had been around storytelling my whole life.

I’d been in music, I’d been learning about drinks, but I was still new to operations in a restaurant. And so I was just dumb enough not to know that you couldn’t do what I was going to do, which was make six, seven, eight classics with fresh juice, muddling whiskey smashes like Dale taught me, to order in a place that was going to be three deep and going bonkers. Right?

So part of that maturity on one front and they and the ignorance or innocence, at least on the other, that allowed me to kind of tilt at windmills for a while. And Garrett indulged it, thinking that we would get it together. First six months were rough, Paul. Rough going for yours truly. But eventually, you know, it’s not that many years and 2008 [David] Wondrich is writing you know most cocktail bars in the world were little five seaters that you wait to get in until they’re ready to make you a drink go to Eastern Standard. They’re making great hanky panky by the bucketload. And, you know, we now know that it can be done, but at the time. It was thought that it couldn’t, but I also didn’t know it. So that’s that’s really kind of how it got going. 

Paul Clarke

You didn’t realize it was impossible until you’d already done it. Yeah. Yeah. And, you know, even as other places in Boston started coming up and becoming prominent and gaining a reputation for themselves and contributing to the city’s bar culture. How did Eastern Standard and your later companion bar, the Hawthorne? How did that continue to play a role and kind of be a part of that story going for? 

Jackson Cannon 

Well, we were, you know, pretty big operation in that sense, right? So I was able to bring people up and have them come into areas of responsibility that we had long retention of the staff. We were really tight group, but we were big enough that there was opportunity inside of it. And when that reached its fruition and for someone, we could help them kind of off into the community at large for their next role if we didn’t have that role for them. So and that that’s a complex idea. I don’t want to get in the weeds on like you can actually retain people too long because then you have so much of the cultural memory wrapped up in those people. If you transition them all at once like I did at one point in time, you face a void.

So it’s healthy actually to be kind of constantly onboarding and helping people mature into kind of their next role. And that part of the work I had no reason to know would be the most gratifying part of it for me. And so, you know, now we have alums all over the country. They own bars, they work for brands, they do amazing things, they own restaurants. I think that kind of kept us tied into the scene that we were exporting people who also believed what we did into other positions.

You know, Drink was like that to a big a big crew of a lot of really important people. And then, you know, at a certain point you have a few different bars, a few different kind of traditions going in one town. And that was sort of when Boston would show up at Tales and kick everybody around because we were sort of we could kind of punch above our weight. I think we learned that collaboration from watching back a house and being tied into the back of house the way that we were, that we just kind of took care of each other. And, you know, we called each other’s bars with regulars. We shared regulars, we shared staff. We we shared ideas. I learned to tea strain that whiskey smash from John. You know, I’ve ever told you that story. 

Paul Clarke

I don’t think so. No. 

Jackson Cannon 

So I go to this meeting. It’s for Garrett and one of the other managers for the opening. I present the first six drinks. It’s Stardust and I’m an Americano. It’s a simple little thing. A Sazerac is on that Jack Rose, of course, and the Whiskey Smash and I make the whiskey smash. And it’s got muddled mint kind of floating around in it. A little bit like specks.

And Garrett says, you know, kind of looks at me and goes, This is all great. And, you know, he can be so, so neutral as to be like it is. What is he thinking? He’s like, this is great, but just tell me there’s not going to little bits of pieces of mint getting stuck in our guests’ teeth because he’d gone through this with the Palmyra at Number Nine Park and they’d sort of figured out how to take the mint back out. Once you’ve got its flavor in the drink and make it clean.

So I called John as soon as I got out of there. I’m like, Johnny, Garrett doesn’t want me to have any mint in the drinks, you know, like John Gertsen, of course. And he goes, Oh, that’s easy, Jack. They got these tea strainers down at Target. You know, just just use that and that the tea strainer as the indispensable weapon was. On its way. So and nobody thinks about it. None of the New York bars were straining like you got an Old Cuban at Pegu Club was on the menu. Was mint in the whole darn thing. And then two years later, everybody’s t straining everywhere you go. And we were doing that in 05, 06 thanks to John, you know.

Paul Clarke

Right. And, you know, this would be a much different conversation if it weren’t for the pandemic, because just as with cities all around the world, the COVID pandemic had serious and in some cases, devastating impacts on the hospitality industry. And that included Eastern Standard and the Hawthorne. When the decision was first made to to close up and not just temporarily for a shutdown, but they’re really closed down Eastern Standard for real. Did that really feel like the end of it at the time? I mean, that it was just over. 

Jackson Cannon

I mean, it was so disorienting. Even people who could continue to work or come back quit to work in different industries. You know, the world just went upside down in in hospitality. Yeah. We were dealing with this kind of broken promise. You’ll always be able to work, right? Like, people will always need you out there. And it was. It was needed, but it wasn’t allowed.

You know, we were it’s a similar story to other people who are in long, late term parts of leases. It was clear very, very early to us that we were going to be kind of shown out of our spaces. And I you just kind of put one foot in front of the other, right? You know, I was fortunate that I found some virtual outlets. And it’s through that process, actually, of having regular guests that I did bar meetings for after shipping them products, and that I realized that I kind of still had the part that was actually most important to me.

I mean, it was weird that they had to make their own drink. And I couldn’t ensure that it was the best possible thing. But I could have the story and I could lead them and guide them and I could participate in their service. And I just realized how utterly addicted to that component I was when it was really the only little part that I had left. Now, we knew the restaurants wouldn’t come back there, but I entertained ideas of a different direction, but not seriously. I mean, this is what I know is what I’m drawn to now for such a long time that, you know, I just couldn’t kind of wait to get back. And, you know, doing some consulting doesn’t get you there. You know, I did that. And the virtual stuff, albeit fascinating and and a lifeline doesn’t get you there.

I need to be with large teams with us trying to make a difference in people’s day to day and the gratification that comes from helping them do that better. And us do that together is what makes me tech. So I am very happy to be through that part of it. I think the problem we face is the oversight has been changed, as they say.

You know, and especially in Boston, we don’t have a lot of casual business in any of the bars right now. Everything really has to be activated, scripted. You’re really pulling as hard as you can to get people into that space where it’s like they were out looking for it. You just had the competition that you could bring was to just make yours more compelling. We are now all in a fight to recreate even the demand to some extent for compelling experience that just happened to you. When you go out to a bar that aren’t your own private scripted experience, and that is a really that’s as existential as a couple of years of of a worldwide virus shutting it down the way that it. 

Paul Clarke

Right. But even with that shutdown, I guess the thing I was wondering about, I mean, there is kind of a happy story there in that there’s a sequel. There’s there’s part two. How did the plan come together to resurrect Eastern Standard in a different location? And what did that mean for you in terms of getting a new start for the place, both recreating the things that you want to recreate, but also give yourself opportunity for a fresh start?

Jackson Cannon

Well, for anybody who has done it, they’ll know what I’m talking about. For anybody that’s about to do it. They’ll think they know, but they’ll find out the hard way when it’s on paper. The dream of a new way forward. I’m going to get the stations right this time. You know, like, is just that a dream that cannot be reality. Everything is defined as much by its plan as by the mistakes and the adjustments to the plan made to cover for those as you go.

So, yeah, there was an optimism about this time. We’re going to do it different. We’re going to be on and then you’re in construction and things happen and you’re everything’s later and you’re living through an epic inflation. You can’t get freezers, You can’t, you know, it’s whatever it is at the moment that you deal with. So that part of it, yeah, there was a moment where like, yeah, we’re going to build it, you know, we’re going to build for the things that we couldn’t do in the restaurant, and the bar. We succeeded in that in some ways.

One of the things we, we added is an amazing ability to do a lot more pasta and bread in the restaurant that we couldn’t do in house before that we can. That’s been a real success story of the first year. I’ve had some successes and I think that’s more interesting. The near misses the bars a little longer in the new spot. So I made four tight stations so that we could all have one to work.

And then we’re a first year bar that’s big and not necessarily under the same pressures and we don’t use one of them that often. And you’re thinking, I wish this was some other kind of setup, you know, like I should have probably gone with a grand middle that two people could work. But, you know, so think those things through, you make your best guess. But once it’s built, we are the river that runs over the rocks and it’s Garrett was always going to I think maybe he thought for a minute about it, but he was always going to have a restaurant.

The Eastern Standard brand was something that was really strong and an important legacy for the community. it’s not a replica. But said this it’s last year a bunch of times. You know, it’s quoting Marvel. But, you know, “Asgard is a people, not a place.” And Eastern Standard is made up of its guests and the people that are going out of their way to learn how to to meet their needs and exceed their expectations in hospitality.

And I have to tell you, you know, people complain about labor, but we are we are really blessed at the one year mark to have retained everybody interested in those ideas, added more people who are interested in those ideas and have had great guest support to kind of bring that brand back. That part of the dream is realized. We are back and we are. We have a 20-year lease. Paul My last, I hope. And and we’re. And we’re doing it. You know, so. 

Paul Clarke

Right. Right. And, you know, the Hawthorne is in the past. Now, one was a COVID casualty, but you do have Equal Measure. What? What does this space give you the opportunity to do? And what does it mean to you to have to have this companion space? 

Jackson Cannon 

Well. So it was part staring at this large parcel and trying to figure out exactly how we would use it. One of the things we didn’t have at the old Eastern Standard was a larger sit down private dining area, and we knew that there was a lot of demand for that going forward. We also in the Hawthorne, I miss her so and the brand is shuttered. Maybe not, maybe not forever, just saying, you know, but the physical space of this, the closer proximity to Eastern Standard and a little bit different space just made sense for us to to think of a new brand to accompany. Yes.

And the Hawthorne was kind of large in its way with, in some ways one of the cocktail bar to be able to be a little bit smaller and by situating it with the private dining room right next to it, that can be closed off or opened up onto it. We can now kind of flex in a way. And this was like when, when we started to work on this just with lines on a paper, we knew that we were having a bar on the side. We didn’t know if it was a different brand.

But pondering it and thinking about it, I realized kind of what we could accomplish. We could sort of have it both ways: We could be the private bar for people of Eastern Standard. We could be a vital kind of new cocktail bar called Equal Measure. And we could occupy the same space and change ourselves sometimes within the course of one night, not even night tonight.

So that’s kind of how the idea was born. I wanted something that cadence and resonated into Eastern Standard as a brand in Equal Measure. If you kind of listen to the two back and forth, you can hear them of the same musical phrase. And that is kind of part of how we got there through sort of the idea of Standard Standard Time and these other kind of elements so happens that, you know, some of the greatest cocktails in the world are equal. 

Paul Clarke

Right. Right. Now, I’ve got to ask you, I’ve known you for close to 20 years now, and we know a number of people who we’ve known in this industry for 20 more than 20 years now. A lot of them have moved on to brand work or more administrative roles or ownership roles. Were there mainly in the office or running errands and not so much behind the bar anymore? Not so much on the floor. How much do you keep your hand in the game as a bartender or as a bar manager? And what’s that mean for you? 

Jackson Cannon

So it’s difficult and was it’s difficult to be proficient, efficient and really like take a hard turn on the corner of a bar unless you do that as your job 40 plus hours a week. And so, you know, during a lot of our other heyday, I was at the point where my contribution wasn’t to take your station if you twisted your ankle as well as you could, that was just it was that ship had sailed.

Once you have multi concepts in your head, getting a little bit older and when you’re not getting the repetition in, even if you’ve crafted a menu, if you don’t get the reps in on it, it’s not a muscle memory thing. And that’s what matters when the orders are coming fast and furious. But there’s lots of other things that happen on the bar as well. There’s a lot of glasses to be polished, but pockets there’s a lot of guests to be seen and recognized are setting them up and taking them down. And so I try to transit the bars as much as I possibly can without getting in the way and do any touch that I can. And I do when it’s not at peak performance, get to make drinks.

You know, I’m especially useful at brunch as if you’re suddenly overwhelmed alone on a giant bar at brunch and you see me come and you’re pretty happy you got another cat who knows those drinks pretty well. But I love being at the tables. I love running drinks. That’s a place where I can watch a bartender in all their glory.

But I can see if a guest, if they need a little bit more information about a guest assist with the garnishing, expedite the pass when it’s busy enough that all the servers are queued up behind me. That’s a real great time that I can have with them. And then to get to the table with an old deep cut is classic that was called for. I really love to run those drinks because I’m like, How do you know about this drink? And they’ll tell me their story.

In 2014, we played darts on Tuesdays and Marley was our bartender and she always made us this. I can’t believe you have this. And I was like, I actually had to text Marley for the recipe, so. it’s really a rewarding part of I can’t do it. I can’t do what I’m supposed to do for the team without being in the operational part of that. But it’s a lot of the less glamorous parts of the operation is where you, where the rubber meets the road. I’m happy to be there. 

Paul Clarke 

Right, right, right. This is going to sound like a job interview question, but I’m genuinely curious. Jackson Cannon, where do you see yourself in another 5 to 10 years? 

Jackson Cannon

Right where I am, Paul. You know, I’m doing what I love. You know, I. It’s funny. I was talking with one of our people the other day, and we were sort of like at capacity for a second. And I could feel it creeping in. I was like, I want to build one more bar, but I’m not leaving to do it. You know, if we. If we can do it, we will.

We have an Italian concept opening on the same plaza as us in a couple of weeks called Standard Italian. Think Eastern Standard, but it’s Italian. And where I get to do like 7 to 9 freezer martinis a day. And, you know, I can do spritzes. You know, in every every shape and form. So we’re hiring, which is just such an exciting time. We’ve been starting people. I’m really excited to get into training with them and launching it. So, yeah, five, five years of find me right here. 

Paul Clarke 

Fantastic. 

Jackson Cannon

What I’m doing. 

Paul Clarke

Fantastic, Jackson. Thanks so much for being on the podcast again. Can’t wait to see you again in person, my friend. 

Jackson Cannon

Likewise, if not Tales, sometime soon.

[music] 

Paul Clarke

You can find Jackson Canon on Instagram at @cannonjacks and head to EasternStandardBoston.com to check out the new venue. We’ve got links to both of those in this episode’s notes? 

And that’s it for this episode. Be sure to subscribe to Radio Imbibe on your favorite podcast app to keep up with all our future episodes. We’ve got plenty of recipes and articles for you online at our website imbibemagazine.com. Check us out on Instagram, Pinterest, Threads, and Facebook for all our day to day coverage. And if you’re not already a subscriber to the print and or digital issues of Imbibe, then let’s get you on board for 2025. Just follow the link to this episode’s notes and we’ll be happy to help you out. I’m Paul Clarke. This is Radio Imbibe. Catch you next time.