The polite description of Hartford, Connecticut, relies on statistics. It is one of the poorest places in the United States, the fourth poorest city in the country, with a population of more than 100,000. One out of every three residents lives below the poverty line. The median household income is less than half that of the national figure. Charting the historical immigration of Puerto Ricans and the emigration of white people—and their money—produces an obvious symmetry. But there are simpler, more accurate descriptions. In Hartford, black people live in the North End and Puerto Ricans live on Park Street. That’s Hartford. That’s what you hear from dedicated organizers. I first heard it from an old member of the Vets for Peace, a longtime resident and community fixture. It’s the truth, but like most things about most cities, you don’t feel like you have a right to it unless you’ve lived there forever.

You can get from Park Street to the North End by heading north on Hartford’s Main Street. This is the in-between. Most of the time, it feels evacuated, and, after the clarity of its racial divide, this emptiness is the second most legible thing about Hartford. Walking up Main, you pass Barnaby Park—its official name—but everybody knows it as Crackhead Park. This part of town has a lot of residual charm. They redid the library, and the Wadsworth Athenaeum is the oldest public art museum in the United States.

The shade of huge office buildings covers the street. Presumably there are people inside, but they never come out. It is difficult to articulate how empty the center of the city can feel even when the insurance buildings are stuffed with people. And when these employees leave, they vanish. People who work in Harford don’t so much commute as escape: there is no weekend on Main Street. Even the Dunkin’ Donuts closes early on Fridays. The little café on the ground floor of my old building, right on Main Street, was open 10 AM–3 PM, Monday through Thursday. The rent, for my two-bedroom in the heart of the city’s downtown, was $525 a month. Across the street was a greasy spoon run by an old Polish lady and nobody else. I got used to getting my own milk from the refrigerator.

So it’s not simply that the Puerto Ricans live on Pearl Street and the black people in the North End: it’s the corridor of nothing that stands between them, and five days out of seven, the white people ten stories up. But this is consistent with the spirit of the state. Aside from a few college towns—New Haven, New London, New Britain, “New” as in England, new as in no old money—where there’s some real diversity, Connecticut is a sea of comfortable whiteness with afflicted pockets of brown. Segregation has seeped into its spirit: the official line is that the Frog Hollow neighborhood of Hartford was named for a nearby swamp, but locally it signifies the French people who lived there, back when there were whites enough for this sort of distinction to scan.

When you drive into town from I-91, you’re greeted by the scenic Colt Armory, built by Samuel Colt, one of the great arms merchants in American history. Not the functioning factory, of course—that’s a few miles away, though still in the city—but the old one, a big brown building with a blue dome on top sporting a cute little gold horse. It’s been subject to one of those endless reclamation projects that is an industry unto itself. When I was a kid I liked the horse; now I think it’s indicative of Yankee honesty, putting our arms-merchant reality front and center when you enter the capital.

Maybe our most purely liberal state—in contrast to the pugnacious progressivism of Massachusetts and the unpasteurized ecosocialism of Vermont—Connecticut, which Obama won by 18 percent the second time—is home to a thriving defense industry. Submarines are built in Groton, Blackhawk helicopters in Stratford, jet engines in Middletown. Colt’s still got that factory in Hartford, although I’m told business isn’t great. It used to provide those solid blue-collar union jobs that get talked about like some sort of rare bird; nobody’s seen one lately, but everybody’s uncle had one or knew a guy who had one. People have an affinity for graveyards; my local library once organized a tour of old factories of Connecticut. The Colt factory was UAW, who went on strike for five years in the ’80s. When all was said and done, they took part ownership of the company, but they never got the wages they wanted. But it’s still open, people still go to work there, churning out guns for the insatiable American appetite. The AR-15 rifle was born in Hartford, and Hartford still makes them, though not, it’s true, the one that Adam Lanza used to kill twenty girls and boys and six teachers an hour to the southwest.

When I lived in Hartford, the city had hung little green signs that called Hartford “New England’s Rising Star.” Things seemed like they might really be rising when we got Eddie—always just “Eddie”—a politician straight from central casting. He had a shameless, shit-eating charm: you knew he was a huckster and you didn’t care. He had the politician’s gift of speaking your language while also not appearing to understand it, which helps, later on, to make deniability plausible. I’d see Eddie at some random meeting, high on some idea two miles to the left of what American politics would permit, and everybody would let it go. It was Eddie. When a city is as hollowed out as Hartford, everybody loosens up a little bit. I spent a lot of time in coffee shops with copies of I, Rigoberta Menchú for sale on a card table, collecting dust alongside communist periodicals. It was in one such shop where a Puerto Rican separatist, ancient and intoxicated, taught me the words to the Internationale. It was permissible, in such a context, to believe in someone like Eddie.

One day you’d see him at collective action events with good food and bad music, places where FBI stood for “For Boricua Independence.” The next day, he’d be cutting ribbon at one of the terminally delayed redevelopment projects, surrounded by executives and glad-handers smiling beatific smiles. He sold himself as a real reformer, the first Hispanic mayor of a half-Hispanic city. He talked about ambitious projects; he embodied civic pride. People accepted the contradictions because they had nothing else.

But then Eddie left in handcuffs. They said his palm wasn’t just open to nonprofits and developers, and that’s Hartford, too.

The advantage of being a broken city is that ambitious people are always trying to fix you. It helps to be the capital. Urban renewal types are shameable that way. The science museum was designed by César Pelli and runs off of fuel cells. The convention center is a weird spaceship landed in the middle of blight. People work there. They have events. I’d rather have these places than not have them; they just don’t form anything like a coherent narrative of renewal. Occasionally you’d hear smart, committed people talking about moving to the new economy, about getting a little Palo Alto going on the riverside, always the riverside. It’s such a comprehensively deluded idea, so poignant in its essential fantasy, that contradicting it feels cruel. But why, in a hundred years, would any tech company set up shop in Hartford, Connecticut? And what difference would it make, if they aren’t paying taxes and all the workers scramble to get to the suburbs at the end of every day?

Not that there isn’t an economy here. On the contrary: Hartford, for all of its abundant need, is annually near the top in “total economic activity,” whatever that means. A lot of money is made in insurance, that old Hartford staple. (The Boston Globe once called Hartford “America’s Filing Cabinet.”) More and more, though, it’s not merely insurance but finance, or “financials.” Every friend who stuck around after college works for one of the big companies with impressive buildings (Aetna’s headquarters is something of a classic) who offer a whole range of services that are increasingly difficult to parse. They move money, from one pile to another, and somehow there’s more, and it’s all for Greenwich and none for Hartford.

None of that money stays in town. When you’re a small city, you’re constantly handing out tax breaks to lure companies, for fear they’ll pick up and move, taking the taxes they don’t pay with them. ING, the $100 billion financial company, partially raised stakes when it moved from Hartford to the nearby Windsor area, which offers access to the airport, scenic tobacco farming, and white people. Many feared that other big companies would follow. But since nobody who worked for ING lived in the city or ate in the city or raised their kids in the city, nothing was lost.

Most of the young professionals who now work in Hartford never lived there, so they can’t be accused of fleeing. There’s very little to recommend it, whether you’re young and hip or you’re looking for stability and childrearing. To live in Hartford you have to be something of a nostalgist, a romantic, or someone looking for unironic left-wing politics, not someone who’s going to worry about leaving your car on the street. You can’t be in search of restaurants that are open on a Sunday. There is no burgeoning art scene or burgeoning anything. The truth is that you can get the “authenticity” of poverty and blight in many other places while still getting a generation of young artists and dreamers looking to get published or recognized or stoned or fucked or each of these simultaneously. I wanted to believe, for a little while, in a Hartford scene, and maybe I just wasn’t cool enough. But even most of the activists left meetings and headed for the highway. For the yuppie types, this goes without saying. The narcissism of parenting is getting to abandon any pretense of caring for places “when it’s for my kid”—that sort of attitude was made for cities like Hartford. Better opportunities abound, for hipsters and yuppies and all types in between, and thanks to the geography of the northeastern United States, many of them are only a couple hours’ drive away. So far from God, so close to New York and Boston.

I love Hartford. I loved it in the abstract growing up twenty minutes to the south and loved it concretely in the four years or so I lived there. I miss Hartford now. I would love to tell you I believe in its resurrection. Hartford’s failings aren’t the fault of it or its people or even its government. They’re the product of our system, of our people. Hartford is the ugly little truth that stomps around in the brain of the American people, the perfect inversion of Silicon Valley, a place with almost 400 years of history and no future. It is ten years younger than Boston, but nobody takes guided tours of its cobblestone. Technically in the middle of a megalopolis, you can stand in Hartford’s center and feel utterly alone.

I have tried, at times, to list its virtues in that cheap lyric way—Bushnell Park, and its lovely carousel; that one churrascaria; the Athenaeum, and its painting of the Lady of Shallot, red hair flying everywhere; those self-same coffee shops; chorizo and rice, plantains and parcha; the Half Door; the rose garden in Elizabeth Park; real racial diversity, in a state that has a tendency to carve out new towns and cities to keep its races separate. But Hartford doesn’t need the cheap romanticism of a carpetbagger. Hartford needs help.

The plight of the failing American city is not getting the money. Hartford has business in spades. The plight is how to get money to stay. Hartford may be a powerhouse of the financial sector, but on the street, there is nowhere to buy a cup of coffee. So much capitalism; such little capital. The last time the city really worked, Mark Twain lived there. Fixing all of it won’t come from building shops near the water nor giving another tax incentive to another company looking for a cheap place to stash a building. If that stuff worked, it would have worked a long time ago.

When I was in high school, in Middletown, I rowed on the crew team. I liked the water, and the boathouse was a respite when I did not want to go home, which was often. We had visitors one day. Hartford Public High was considering making crew a varsity sport.They bussed students down to our boathouse to watch. This was when the district was most afraid of losing their accreditation, leaving a whole school full of kids unable to apply to college or join the military. The school had been in session for 140 years longer than America has been a country, but there was no comfort in that pedigree, no percentage in nostalgia.

The thinking, I guess, was that Middletown, an “urban” school district with a percentage of black students proximate the national average, would feel more welcoming than the average white and affluent team. But crew was not a minority draw. No more than a couple of Hispanic kids and no black ones. But then, exposing the Hartford Public High School Crew Club to the realities of a sport dominated by private academies named after English churches made strategic sense. Not that they would have heard slurs: old New England money dislikes racism the way it dislikes loud house paint or flashy Japanese cars; not because it’s wrong, but because it’s gauche. Instead: those silent looks, that air of generous patience.

So we rode our boat, as the other students watched us awkwardly from the embankment. Ours was a pure incomprehension. Hartford and its children were a lifetime away. I knew only that they were poor and that their school was poor and their city was poor, and that when that poverty came up, the grownups around me would clench in a defensive silence. People were never unkind. They were just as distant as our tiny little state allowed them to be.

One of the coaches suggested we could talk to them later, tell them how it was. You know. Connect. But when we got off the water, they were already boarding the bus, heading home

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