A Turncoat’s Manifesto

Why I left Boston, and why that's not the unforgivable offense it once would have been.


illustration by heather burke

Bless me, Father, for I have gone and done the unthinkable. I have moved to New York.

Not long ago, this would have been an act of profound betrayal, even cowardice. Betrayal because to voluntarily move somewhere else implies that Boston is not the greatest city in the world (a big no-no); cowardice because Boston is a tough place to live in, constantly testing, goading, freezing, soaking, charming, spiting, begrudging, elevating, demeaning, embracing, ignoring, and generally trying you, and to leave it exposes a fatal character flaw, a tacit admission that you’re not made of sound enough stuff to withstand its torments. Or so goes the thinking. I had always planned to stay until the very end, that point at which I would be summarily dispatched by an errant bullet in Downtown Crossing, or fall waist-deep into a yawning pothole and then get run over by a speeding cab, or maybe even kick off peaceably. Yet here I am.

Needless to say, I’m dead to many of the stalwart Bostonians I left behind. Before leaving, my wife and I spent weeks going to bars and parties, saying goodbyes. At one, my brother-in-law said, “This feels like a cross between a wedding and a wake.” At another, a local PR professional embroiled in a political debate occurring just feet from me said, “You know who would be good to talk to about this? Keohane, if he were still alive.” A Dorchester-bred friend accused me of “trading a great city for a mediocre one.” “You’ll hate it,” several others opined. I started badly missing these people even before I left, even if a lot of them are bastards. (I like bastards; I trust them.)

But as hard as it was to leave the people, Boston itself was a different story. I spent my last few days taking long walks around town to see if I could feel that old spark of inspiration. I strolled over the Mass. Ave. bridge from Cambridge in late afternoon, when the city’s skyline turns to gold. When friends from out of town used to visit, I would always take them to see that view at that time, and then get them plastered upstairs at the OtherSide Café, part of a relentless if futile lobbying effort to get them to move here. I walked through the Common and the Haffenreffer Walk in the Public Garden, along Charles Street, and up and down the side streets of the Back Bay. I hit Southie, Dorchester, and the bars in Central and Harvard, listening to the Bosstones, or the Lemonheads, or Jonathan Richman on my headphones. It was, in short, an attempt to absolutely torture myself and get a head start on my penance for the fully premeditated cardinal sin I was about to commit.

I got nothing. No flood of memories, no guilt. Just an uncharacteristic silence, and a general sense of being preemptively turned away from. In his great and exasperating book, The Old Patagonian Express, Paul Theroux, a Medfordite, observed that as he took the T from Wellington Circle to begin a two-month train odyssey to Patagonia, the ads on the Orange Line seemed strangely quiet, as if they knew they shouldn’t waste their energy trying to draw the eye of a guy who’s not going to be around anymore. I didn’t notice that on the T, because I was consumed as usual with hating the T, but I did feel something similar from the newspaper boxes around town. They used to scream at me, and I at them. Now they seemed preternaturally still. If I had expected one last go-round with the city, a teary farewell from an old friend, I got the equivalent of “I’m not going to give you the satisfaction, you prick,” topped off with not one but three grisly bicycle near-accidents in a two-day span, and 12 hours of torrential rain on moving day. See ya, pal.


Boston has always been the kind of place that pushes you away and then never forgives you for leaving. A city of avowed begrudgers, we have a symphony of grievances as our civic dialogue. Resentment is a primary virtue, woven into our very DNA. But while I once felt the city and I were united in our resentment of various foes (who included, frankly, a broad swath of the area’s population), I now realize that alliance expired long ago.

Truth be told, in the handful of years that preceded my departure, I found my ardor for Boston diminishing. I discovered, to my dismay if not surprise, that I was turning into an intolerably nostalgic mick at the age of 31, roughly 40 years ahead of schedule. I spent much of my time pointing out to newcomers all the great things that used to be there, and there, and there, before Boston became a prettily arranged mall of cell-phone stores and million-dollar condos. Increasingly, I could go weeks without the city surprising me. When I found myself feeling especially warm toward Boston, my mind never stayed in the present. It inevitably went back to Morphine at the Plough & Stars, waiting in line for a new record at midnight at the old Tower Records, drinking coffee and staring at the State House from the frozen windows of Curious Liquids on Beacon Hill (today a shiny Fox 25 studio), or late-night beers and BLTs at the long-defunct Deli Haus in once-wonderful Kenmore Square, now locked in an epic battle with Boylston Street to see which can host Boston’s ghastliest hotel structure.

Right up until the global economy completely broke down last fall, metro Boston was riding a wave of sustained prosperity and good fortune unseen since the days of Bulfinch. Yet it was one that came frighteningly close to obliterating the city’s unique character and style. Our studied reserve failed us. Money and winning sports teams made us dull and obvious, just another nouveau riche burg aquiver at the possibility of whoring itself out for another Gucci store. Things had gotten too easy, they came too readily.

It’s a sentiment almost ludicrous in its Irishness, to resent victory or fetishize struggle. But then, if the Irish had trounced the English at will, their books wouldn’t have been any good, and the people themselves wouldn’t have been as funny. It wouldn’t be Ireland. It’s the same here: With all the city’s recent successes, the point has been lost. Boston has ceased to be Boston. And now we don’t even have a tax surplus to show for it. There’s something to the idea that the Hub is in a better position than most American cities to weather the years ahead, but I still can’t escape the sense that we’ve been strip-mined.

I know: bitch, bitch, bitch. Everyone ruins everyone else’s city. That’s always the way, no matter where you are. But that feeling had really accumulated in me over the past few years. After I left, it felt like a relationship that had long since cooled, and the only thing holding it together was force of habit. You break that habit, and suddenly you realize you’d actually checked out months or years before.


But do I miss it? Not any more than I did when I still lived there. It’s a common enough sensation. When you grow up in a city, it’s not that you can’t go home again—it’s that you can’t go home again even if you never left home to begin with.

In any case, at this point the physical Boston doesn’t much matter. It’s what I’ve taken away from it that does. I’ve spent the better part of my life trying to live up to the Bostonian ideal: tough-minded, smart and unpretentious, brooding and funny, and equipped with the world’s best accent and a suspicious and disdainful nature that, under the right circumstances, has been known to give way to an indomitable sense of loyalty. (I’ve sometimes indulged the pet theory that Bostonians are so angry because the rest of the world turns out to not prize loyalty the way we do, though I’ve also suspected that might be malarkey.) It’s those things that I’ll remain loyal to, regardless of where I end up, be it New York or even back in Boston, down the road. It’s those things that will ensure a future of feeling like Pigpen in Peanuts, carrying a visible dust cloud of Boston around me, hoping that the wind doesn’t blow it away.

It’s an effect that will only be heightened by the Sox sweatshirt I bought for the sole purpose of antagonizing my new neighbors.

Ultimately, what’s become clear since I moved away is that it’s that very same set of Bostonian ideals that helped shape me into a person destined to be disappointed and disheartened by what Boston would turn into. That’s the tragedy of loving this city. Not liking it, but actually loving it. And it is worth loving, worth making that effort, even if it breaks your heart in the end.


As much as it still sort of pains him to say it, former Boston staffer Joe Keohane is a freelance writer based in New York City.