In 1950, Philadelphia was a predominantly white city, with blacks comprising about 20 percent of the population. A decade later, that number had risen closer to 30 percent, and four years after that—in the summer of 1964—racial unrest flared in North Philadelphia, largely over brutality against blacks by white cops. Hundreds were injured or arrested, and more than 200 stores in North Philly were damaged or destroyed in three days of rioting, with many never reopening. White flight only accelerated in the next decade, and today blacks make up 44 percent of the city’s population, and non-Hispanic whites 37 percent.

John, who lives on Woodstock, a leafy side street between Poplar and the northern stone wall of Eastern State Penitentiary, has seen the city’s demographics shift firsthand. He’s 87, and has lived on this block since he was five. Since 1930.

It was a different place then, before the war. You could walk home from the Blue Jay restaurant, at 29th and Girard, at any hour. Or up to Ridge to the Amish Market.

John worked in the offices of local long-distance haulers. He’s small, with a bowling-ball potbelly and macular degeneration; his right eye is closed and sightless. He chain-smokes Virginia Slims as we sit in his enclosed front porch and he describes his neighborhood, back when he was a boy.

Milk and bread and ice delivered to your door. A city worker coming by every evening to climb a ladder to light the gas lamps that cast a beautiful glow. There were four nearby houses of prostitution, and tailors and drugstores, a butcher, barbers, a candy store—a self-contained world. Everybody had a laundry tree in the alley out back, and every Monday there’d be a snow of white—until shirts and towels and sheets began disappearing, right after the Second World War.

That’s when blacks from the South, with chips on their shoulders, John says, moved North. They moved into great brownstones above Girard and trashed them, using banisters and doors to stoke their furnaces instead of buying coal. Before long, it looked like Berlin after the war. Whites moved out.

I ask John when he was last above Girard Avenue. He thinks for a moment. “To a football game,” he says. When? “In 1942.”

Over the years he’s been mugged twice, once for a hundred bucks, once for the bottle of liquor he’d just bought. His house was once broken into, and he lost coats and money and Christmas presents and his father’s gold watch. A steel-tipped arrow once shot through his rear kitchen window, impaling a chair just after his nephew had gotten out of it. He watched as four or five black men appeared on the block one afternoon and tried to break into his brand-new Chrysler Imperial. John stood at his door—they walked away when they saw him. Last summer he was sitting on his stoop in a lounge chair and went in to use the bathroom, and when he returned, there was no chair—a neighbor watched a black kid on a bike zero in to lift it.

There’s more. But John doesn’t express sweeping bitterness or anger. “Oh, I have no problems with blacks,” he says. He was once quite friendly with black neighbors on Poplar, whose alley garages he can see from his porch. “They were working people, nice people, lovely people. I hated to see them move.”

Given the monumental changes he’s seen and his declining health, John no longer risks venturing alone beyond his block. There is a monumental spread, too, in his thinking, when he considers the range of black people who have entered his neighborhood.

He tells me about the time, a Saturday afternoon more than 10 years ago, when he came downstairs to his living room to find a stranger had come in through his front door—“It was a nigger boy, a big tall kid. He wanted money.”

It’s a strange moment, not only because of the ugly word, but because of John’s calm in delivering it, as if it is merely fact, one that explains the vast changes in his world.

Fairmount is now a destination of choicefor a certain breed of young professional. And among them I discover a tried-and-true test of racial comfort.

Jen lives on Mount Vernon with her husband, an architect, and two children, eight and six; she’s been in Philly since she came to Drexel from Egg Harbor Township on a basketball scholarship two decades ago. Four years ago, Jen began looking into where Sebastian, now in third grade, would start school.

There’s a very good elementary school in Rittenhouse: Greenfield. And that’s the school the parents in Fairmount—the white, middle-class parents, which is Fairmount—shoot for if they’re going public.

Jen took a look at Bache-Martin, the public school four blocks from her house and 74 percent black: Teachers engaged. Kids well-behaved. Small classes. Plus a gym and an auditorium and a cafeteria, a garden, a computer lab. She enrolled her kids there.

Jen was not in the majority. Other mothers told her, “There is a lot of Greenfield pressure.” That pressure is from fellow Fairmounters: pressure to send their kids, collectively, to the right school. Greenfield test scores are a bit higher. It’s also not nearly so black.

Another mother told Jen: “I didn’t want to be the first”—in other words, the first to make the leap to Bache-Martin. “It takes a special person to be first.” Another told her: “Not everybody is as confident as you.”

Sipping tea in Mugshots on Fairmount Avenue, Jen rolls her eyes over the nut of the problem: Unfounded fear. Groupthink. A judgment on a school without even setting foot in it. “I wouldn’t like to imply that it’s about anything else,” Jen says, but of course it is: race.

There are ways around it, however. Jen became a kindergarten parent. She’d open the doors and get parents in there. Movie nights. Soccer and dance and art programs. Hip-hop dance instruction. A playgroup two mornings a week for toddlers. Local landscapers giving free mulch and leftover shrubs. She’d sell the school.

Even with all that, though, parents who’d check out Bache-Martin on open-house night still weren’t enrolling their kids. “I’m not sure who else is going there,” one mother told Jen. Same old fear.

Jen’s next step: a mixer at the Urban Saloon on Fairmount. The kindergarten teachers came, and parents brought kids. Jen laughs at herself, given the bald simplicity: Get the parents together having drinks and talking with the teachers and each other, then watch what happens. Get them nodding that if Bache-Martin is good enough for Marc Vetri’s kid—the restaurateur is a Fairmounter—then maybe … And sure enough, something shifted. Some 10 of the 15 families who showed up enrolled their kids. A new groupthink was forming. These home-and-school meetings over Saloon drinks happen two or three times a year now.

It helps that Greenfield is getting crowded and that the city is naturally expanding outward. “People in the neighborhood are now getting nervous whether there’s a spot for them here,” Jen says.

Nobody, through all this, said a word about race. At least not publicly.

I meet another urban pioneer of a different stripe.

Ben, 38, grew up on Madison Avenue in New York and went to Vassar. He came to Philly 13 years ago for a teaching job in Logan, and worked for Sister Mary Scullion’s Project H.O.M.E. for a couple of years. Then he got into rehabbing houses.

Seven and a half years ago, he bought a rowhouse a couple blocks north of Girard. He thought the neighborhood—rundown, not integrated—was about to change. For a couple years, Ben was pretty much the only white guy there, though he was comfortable. Ben roams all over Philly—I catch up with him one day for lunch at Syrenka in Port Richmond, where he’s building sets for the TV show Do No Harm. 

His rowhouse is on a corner, where kids hang out; he got to know them. There’s “tons of great neighbors,” Ben says, from folks who work three jobs to welfare recipients, often subsidized by the local drug trade.

He’s rehabbed three houses nearby; one had been a crackhouse where squatters got sent to jail, leaving behind 15 gallons of urine in various cups and bottles. “I don’t know why,” Ben shrugs. “But crackheads can sometimes be meticulous.”

Then things turned on him. A middle-aged black guy who’d been in the neighborhood drug trade for a couple decades was friendly at first. The guy went to prison on drug charges for a bit. When he came back a couple years ago, he started running drugs next door to Ben’s workshop. The dealer was different now. It was dick-swinging time.

He and his henchmen started parking in front of Ben’s shop, blocking his access. Ben asked them to move, but they would give him a hard time. The dealer started bad-mouthing Ben to the neighborhood, talking about what was going to happen to this encroaching white guy. “He got two strikes, third strike he’s done,” the guy told people. “If he survives, if he makes it out of the neighborhood … We kill motherfuckers around here.”

Ben had hired Thomas, a recovering addict from the halfway house across the street from the shop. Thomas told him not to freak out—the dealer would screw up. So Ben waited.

One day about a year ago, Ben was in his shop when the FBI rolled up in two black SUVs and kicked in the door of the dealer’s building. The dealer wasn’t there, but his sister was out on the street. “Where is he?” the cops demanded. She got him on the phone. He’s now doing 10 years on an Oxycontin prescription scam.

What, I ask Ben over split-pea soup at Syrenka, would have happened to him if the cops hadn’t zeroed in?

“I don’t know,” he laughs, though it’s not a happy, or cocky, laugh. He remains in his house on Thompson, with no particular desire to move. As a boy, Ben took the neighborhoods of New York by storm, and that’s his method in this city: He wants all of it. Fairmount, he says, is too homogeneous for him. He’s a man on the outer limits of engagement—even at the expense of his own well-being.