Alex Belomlinsky/

I'm a native New Yorker, but my fate has been entwined with Cleveland since 2008, when I went there to canvas for Barack Obama, mostly because Sarah Palin scared the bejesus out of me. As you may know, Ohio tends to be a swing state, and I don't think it's entirely coincidental that the state itself is shaped like a hanging chad.

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I'm back to sell locals on Hillary Clinton, this time with a new sidekick: the best-selling novelist Gary Shteyngart, a friend of mine from high school. He's here for research purposes—he's basing a character in an upcoming novel on my Bengali in-laws, who happen to live in Cleveland—but is joining me for a day to help "stave off the apocalypse," as he puts it. He went to Oberlin for college, so he has hazy memories of Cleveland. They mostly involve sports bars, Marxism, and long hair (his). When locals are out of earshot, he calls the city "The Mistake by the Lake" and pokes fun at its diminutive skyline, though I think there's a secret fondness for the city that undercuts his jokes.

While a recent poll gives Hillary Clinton a slight edge over Donald Trump, the state is still a deep shade of bruised-eye purple. Moreover, Trump needs Ohio if he stands any chance of winning. And so Gary and I find ourselves at Ohio Together's campaign office, situated in an attractive red brick building in downtown Cleveland. Our squad leader, Mohammad, gives us a quick training. He's a genial second-generation Indian American and is wearing an Ohio State sweatshirt. He gives us a script to follow and some brochures that outline brief talking points. He tells us what to say to an undecided voter (ask if they have any young relatives and then tell them about Clinton's plans for making college more affordable). We're also given a stack of cards that encourage early voting—"Tell people that Obama won the early vote but lost to Romney on Election Day, so without the early vote, Obama would've lost Ohio!" Mohammad says. We're instructed to have people fill out these cards as a sort of pledge to vote before November 8. Mohammad also tells us that if people vote early, they don't have to show ID at the polls, just produce the last four digits of their Social Security number.

I'm not sure this makes sense, but we will dutifully regurgitate this line at every doorstep, because these cards are our de facto measure of success—the more we collect, the more commitments we've gotten from people to vote early, and the happier we make Mohammad.

He finishes divvying up turf, and we get our leads. "It's not the worst neighborhood," Mohammad says somewhat obliquely. We pile back into the car and drive down an increasingly desolate street toward our destination, located in Hough, which I later find out was the site of major riots 50 years ago. The riots killed four and injured more than 50 people, and hastened white flight to Cleveland's suburbs. In just 10 years, from 1950 to 1960, Hough went from 95 percent white to 26 percent white—though judging by what we see, that figure now looks closer to 0 percent.

We park on a narrow street, next to a house with several broken windows that are covered over with cardboard. There are more empty lots than houses. Gates are jerry-rigged with chicken wire and plastic tubing. Porches are collapsing and front stoops are missing steps. The Glengarry leads these are not.

We ring the doorbell of the first house, but no one answers. "Well, so much for that!" Gary says as we turn away. But then a car pulls up and the window recedes, disgorging a cloud of cigarette smoke. A deep voice floats out on a pillowy Midwestern accent, "Can I help you?"

"Yes! We're looking for Robert," we say, a hopeful chorus.

"That's me," the man says, eyeing us warily as Gary launches into the script. After a few lines about Clinton, the man visibly relaxes. "Oh yeah, I'm gonna vote Hillary. I'm a government employee, so I'll be working for this election." He takes a card and fills it out. Success! We are elated. We take the card and thank him profusely. He does a half wave. As he drives off, I notice that his license plate identifies him as "Loverboy" and a well-honed social-media instinct kicks in. I whip out my phone for a photo. "Maybe we shouldn't take pictures," Gary murmurs.

Adrienne Day

We make our way through several houses. As we walk around, our turf unfolds with a depressing regularity: weedy lot, weedy lot, falling-down building, abandoned building, weedy lot, church. The houses are run-down, the residents wary when they answer the door—all seem to relax when we tell them what we are doing there. It soon becomes clear that a major obstacle in getting out the vote here is real rather than theoretical: People are at work, people have moved, one 19-year-old girl is incarcerated. I end up checking off the "not at home" box for her. It's technically accurate, I guess.

We collect two more cards. This is deep-blue, Obama-lovin' country.

"Anyone who votes for Trump is a racist," says one African American woman who answers the door. We nod. Another card.

We end our shift at a house that is a mini-McMansion in comparison to its brethren: new yellow brick, intact stoop, several visible security cameras. The door works. A middle-aged white man, the first non-black person we've seen, opens the door. He looks physically fit and serious. We launch into the script. After a minute, he holds up a hand. "Oh, I'm voting," he says. Dramatic pause. "Just not for her." We are stunned. "You mean you're voting for Trump?" He nods.

At last, we've netted a real Trump voter. It feels like I've torn open a candy bar and found a ticket to Hamilton inside. I start to ask the man more questions, but Gary, whose sense of self-preservation is obviously greater than mine, thanks him and quickly pulls me away.

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Hough is a microcosm of American politics in 2016. Poor and working-class black folks love Obama, and Clinton is seen by many as furthering his agenda. Poor and working-class white Americans feel abandoned by Washington. As a recent Saturday Night Live "Black Jeopardy" skit demonstrates, many working-class people, irrespective of race, share a similar world view when it comes to feelings of disempowerment and being ignored by coastal elites, but the issue of police violence against people of color drives a stark wedge between black and white voters. And it seems fairly safe to say that most black voters are not backing Trump, who has endorsed taking stop-and-frisk policies nationwide and has generally come down on the side of cops. Thus our one white Trump voter in his McMansion-like prison, surrounded by a sea of black Clinton supporters. It doesn't bode well for the future of bipartisan politics, despite a deep well of common interests.

We head back to the office. Mohammad is happy with our five cards. Due diligence complete, we head back to Gary's Hyatt, which is located in a mall and looks down on a local branch of a Charles Schwab. "The real America!" he says with a smile.