Every Type of Boston Asshole, Explained

Jim Rogash/Getty Images Sport/Getty Images

I don't live in Boston anymore, and only come through five or six times a year to see my family and friends and ride the swan boats, so sometimes I forget just how many incredible assholes our city produces. I don’t even mean this in a bad way. Boston is my hometown, and I’ll defend it to the death, but we also happen to have an exquisite number of Hub-specific jerks, who can be infuriating and horrible, but also make me kind of homesick. So here they are, in a somewhat specific order: 

The Brahmin Asshole 

As seen at: The Union Club, The Country Club, 75 Chestnut, J. McLaughlin, behind the wheel of various '90s model Saabs & Volvos
The key to the Brahmin Asshole is in the subtlety of their condescension. When you see them on Beacon Hill driving around in their ’94 Saabs, wearing their tattered Murray’s Toggery Nantucket Reds and old Sperry’s and rumpled J. Press blazers, you can’t help but feel like you’re witnessing a real life Smithsonian Natural History Museum exhibit. 

“Look,” you’ll shout to your friend as you walk down Mount Vernon. “Did you see that? I think it was an Adams, or an Appleton, or a Bacon, or a Bradlee, or a Cabot, or a Chaffee, or a Choate! Or maybe a Coolidge, or a Cushing, or a Dudley, or an Emerson, or an Eliot, or an Endicott! Or chances are it might’ve been a Gardner, or a Holmes, or a Lawrence, or a Lodge, or a Lowell! Or perhaps it was a Lyman, or an Otis, or a Peabody, or a Phillips, or a Putnam. But it definitely could’ve been a Quincy, or a Saltonstall, or a Sargent, or a Thorndike, or a Tudor, or a Weld, or Warren. Kinda hoping it wasn’t a Winthrop, though.” 

What you may not realize is that they’re ever-so-cautiously gawking back at you. Because they can’t believe you aren’t appreciating the fact that the very cobblestones you’re walking on were laid in the ground by one of many Irish people their family briefly employed generations ago. So try and show some respect, Sudra. 

The Townie Asshole

As seen at: Every Faneuil Hall bar, ever. 
A stereotype within a stereotype. Though commonly believed to be from Southie, in reality, 95% of Townie Assholes are actually from a town that is not, in fact, Boston. Be it Chelsea or Quincy or Revere or Norwood or Weymouth or any of 20 other towns with men’s league hockey games that end in parking lot fights one out of every two nights. 

When they do pile onto the Red Line to come into Boston for a night on the town, they inevitably end up at the same Faneuil Hall bars they've been going to for the past 15 years. At said bars, they will be loud and aggressive and sloppy and play up their Boston accents for the tourists, and inevitably end up fighting a group of gentleman who are exactly like them, but maybe from North Quincy instead of Quincy. Said fights break out like clockwork around 1:45am, right by the sausage vendors as the cops look on with minimal interest. It wasn’t until I moved to another city that I realized this was very much not a normal thing. 

The Taxi Cab Asshole 

As seen in: Um, taxi cabs
We get that, thanks to Uber and Lyft, your entire industry is dying and medallions are shrinking in value. And that fills us with empathy. Which is why we opted to flag you down rather than pushing a button on our phone, which is way fucking easier to do than flailing around for your attention. But do you think the logical response to our somewhat charitable choice is to ask us where we’re going before you unlock the doors, ALWAYS say your credit card machine is broken, and pretend you have no idea how to get to Coolidge Corner, even though we’re on Beacon St right now?!!?

Flickr/Andrew Malone

The Boston Sports Asshole

As seen at: Fenway, Gillette, TD Garden, and all sports bars surrounding said stadiums.
Guess what? We also like the Pats. And the Sox. And the C’s. And the Bruins. And we can get pretty excited when they do well, and pretty upset when they do poorly. But there is a reason that when you type “obnoxious” into Google, the actual third thing that comes up is “Boston fan” after “definition” and “TV.”

Screenshot via Google

Back in the '90s, we used to be lovable losers, a city of passionate fans who really knew and cared about sports and supported our teams no matter what. And then we started winning. Everything. Super Bowls and World Series and another NBA title and Stanley Cup, and maybe even the Boston Cannons did pretty well at lacrosse? And suddenly we became as bad as the New York fans we’d detested for so long -- brash and obnoxious and rubbing it in everyone’s faces. And sure, in the mid-aughts everyone caught that obnoxious Boston sports sickness for a bit. But we, like, deserved to relish all of these titles after so many down years. But the asshole-crown is reserved for the special subset of Sports Talk Radio Call-In, DeflateGate Truthing, Opposing Fan Fighting winners that make wearing Boston sports gear in any other city suddenly look like a provocative act. 

The Hipster Soccer Asshole 

As seen at: Parlor Sports, various Irish pubs throughout the city 
On the far opposite end from the Boston Sports Fan, the Hipster Soccer Asshole definitely never played soccer, and actually wasn’t really into the sport until a year and a half ago when he read a story in Vice Sports about Swansea and realized you get to wear scarves. 

They don’t like soccer because of the beauty of the sport, its subtle storylines, and the rich history. It's mostly because it seems to piss off traditional sports fans and make them feel like they’re doing something cosmopolitan and obscure. You can tell an asshole fan from a regular fan by the aggressiveness in which they want to discuss tactics they cribbed directly from Mike Goodman’s old Grantland columns, and their terrified faces when you ask why they started supporting the team they like. And yes, on a somewhat limited basis, this can also apply to a small subset of Revolution fans. 

The Cambridge Tech Asshole

As seen at: Every single Kendall Square business except Advance Tire and Car Care Center 
Mainly just engineers who either lack the ability to read facial expressions and take social cues, or deem them too time consuming to get in the way of playing Infinifactory on their comically large phones. 

Be Gentlemen Limited Partnership

The College Asshole

As seen at: Any crappy bar with relaxed ID-checking policies located within walking distance of a college. Formerly, Daisy Buchanan’s (RIP).
It’s not even your fault. You’re just in college. You’re "experiencing things." And you don’t have a lot of money. So you gravitate toward the bars with the bucket nights and the alarmingly cheap well drink specials. You hang out in giant packs and you can’t fathom why people would be upset if you sprayed your drink in the air, or tackled your buddy by the coat rack, or pissed in a place that isn’t the bathroom. And why wouldn’t you aggressively make out with a near-stranger right there, blocking the exit? YOU’RE JUST TRYING TO FIGURE OUT WHO YOU WANT TO BE LATER IN LIFE, OK?!? The better question is: why am I hanging out at this bar, too?

The Rich Foreign College Asshole

As seen at: Clubs. So many clubs. And Newbury restaurants with outdoor seating.
Many years ago, I did a story for Boston Magazine in which I hung out with extremely rich foreign college students. This was when a ton of money was pouring out of Russia, and so every new oligarch was sending their kid to some school in Boston as a status symbol to their peers in the homeland. And these kids had everything: penthouse apartments overlooking the Charles, 15K-a-month stipends, Range Rovers, GIFT CARDS TO LEGAL SEAFOODS, you name it.

Like any range of people, some of them were actually good kids from super fortunate backgrounds, but those that fit into the “asshole” category were among the worst I’ve ever encountered. Take a 19 year old, give them unlimited funds, a sense of entitlement, no rules, a concierge apartment with a real Banksy on the wall AND an Amazon Prime account, and see what kind of fucked up social experiment results.

The Charlestown Asshole Who Wants You to Think He Robbed Banks Like in The Town but Definitely Actually Grew Up in a Loving Middle Class Family

As Seen in: The Warren Tavern, “trolling for Toonies”
It’s OK that your dad loves you, Derrick.

The Old North End Asshole

As Seen in: Plastic chairs outside Caffe Dello Sport
Gentile signore,
Sarebbe simpatico se lei smettesse di fissare e fischiare a tutte le ragazzine. Mi rende nervoso. I loro cannoli sono buoni, però. Buona giornata.

The Ex-Boston Asshole Who Moves Away and Now Spends His Time Nostalgically Criticizing People He Might Just Miss

Sigh. Sorry, Dad.

Sign up here for our daily Boston email and be the first to get all the food/drink/fun the Hub has to offer.

Kevin Alexander is Thrillist's National Writer-at-Large and at least four of these assholes. Guess which ones @KAlexander03.