A Night at the Door With Three Boston Bouncers

The eyes and ears of three very different bars tell us about their normal—and not-so-normal—nights on the job.

Boston’s nightlife scene has a mixed reputation compared to other big East Coast cities. The bars in the Massachusetts capital close at 2 a.m.; the city has an infamously tightly regulated liquor license quota; it’s illegal to discount alcohol for a portion of the day so happy hour doesn’t even exist. Toss in the fact that nearly every night you’re dealing with either students from the many colleges or rabid Pats, Bruins, Celtics and Sox fans out cheering for the local team, and it makes sense that outsiders might have their doubts.

The city is, in many ways, still the original wild child of the region—just ask anybody who works the door at any number of the Hub’s watering holes. For this installment of PUNCH’s “A Night at the Door,” which explores what these gatekeepers experience nightly in cities across the country, we started with Jared at Lucky’s Lounge, a dimly lit hideaway/weekend dancing den in the Seaport District; headed North across the Charles to Saloon, a speakeasy-style cocktail lounge in Somerville; and, finally, ended the night at Bleacher Bar, a sports fan haven sitting just beneath the centerfield bleachers of Fenway Park.

We asked each bouncer to share their craziest stories on the job, favorite after-work beverages and their takes on what makes the place they work at worth a pit stop—or seven. Here is what they had to say.

Taylor Gallagher

Age: 27
Workplace: Saloon 


How long have you been working here?
“Just under two years.” 

What’s the weirdest thing you’ve seen at the door?
“I’ve seen all sorts of stuff. I saw a kid get his teeth kicked in in a fight across the street, like, teeth actually left his head. That’s definitely at the top of the list.

“We also had a guy try to come in a few months ago, got right through the door, and when he took off his jacket he had this… I think I could only really describe it as a leather daddy kind of set up. And like, I’m not judging, but I can’t have you down there basically topless, man.”

What makes this place special?
“It’s a cheesy answer, but it’s the people; it’s the staff that works here. We all have good days and bad days but everyone here is on their game and they care. That really helps.”

How do people react when you tell them what you do?
“Everyone always assumes I must know like 97 different martial arts, that I must get into fights every night of the week. They think I must be ex-military. I am none of those things, but it works that people think that way. If I do my job correctly I never have to fight anyone. Ever.”

What’s your go-to post-shift drink?
“My go-to’s a Guinness.”

lucky's boston

Jared O’Brien

Age: 32
Workplace: Lucky’s Lounge


 How long have you been working here?
“Three years.” 

What’s the weirdest thing you’ve seen at the door?
“I’ve had women flash me to try to get in when we’re at capacity. It doesn’t work.”

What makes this place special?
“I consider us to be a family here, and I like being able to make sure they’re safe. I like safety. I also like being able to ensure people have a good time. I enjoy the atmosphere here. It’s a different crowd. We get a little bit of everything, you know?”

How do people react when you tell them what you do?
“They say ‘You must be tired,’ which is very true.”

What’s your go-to post-shift drink?
“It’s usually a vodka-soda; Tito’s if I get to pick.”

Gerard Wynn

Age: 22
Workplace: Bleacher Bar


How long have you been working here?
“I’ve worked here five years, but five summers, like on breaks from college. I graduated in May so this will be my first full year.”

What’s the weirdest thing you’ve seen at the door?
“Honestly, I’ve had more guests take their own friends outside when they get out of hand, which is great. I’d rather not get too physical.”

What makes this place special?
“I’ve got a lot of friends working here. A lot of us have been here, off and on, for a long time. It’s great working for the Red Sox, too. I get to work and cheer on the Sox, it doesn’t get much better than that. And you know it’s a great job, good money. I can’t complain.”

How do people react when you tell them what you do?
“People always say ‘Oh wow, that’s gotta be interesting.’ And it is. It’s not as crazy as you’d think, but it’s definitely interesting. I’m studying homeland security in grad school right now, so I’ve worked with the BPD, the MA State Police, the Dorchester District Court. I guess doing security is in my blood.”

What’s your go-to post-shift drink?
“I’m a pretty simple guy; I’ll grab a Bud Light.”

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Haley Hamilton is a Boston-based bartender and freelance writer. She writes The Shakes, a weekly column about booze and bar culture for MEL Magazine and is a regular contributor to Boston’s alt weekly, DigBoston.