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Arise, Tenderloin

It is San Francisco’s most glaring contradiction, an island of need in a sea of prosperity. Can it be helped? Does it even want to be?

A painfully familiar sight in the Tenderloin: the line for a free meal at Glide Church.

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A blunt-talking former pimp and drug-dealer, Del Seymour now gives tours of what he calls "the other wine country."

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An open-topped bus full of tourists takes in the sights.

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Two women pass one of the Tenderloin's colorful murals.

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Treasure biscuits.

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A battered Bible lies on top of bedding.

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Moving a mattress.

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Barring a seismic shift in city politics, the Tenderloin is not going to gentrify the way that similar neighborhoods have in other cities. Not next year, maybe never.

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Between 6 a.m. and 3 p.m., the pews at St. Bonfiace Parish become a refuge for the weary.

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On a warm San Francisco night this past September, I dropped my daughter off at Hotel Nikko on Mason and Ellis for a performance by one of her musical theater idols at Feinstein’s. There were probably a hundred people circling the streets looking for parking, but I had my secret spot: Driving two blocks south on Mason, deep into the wounded but still-beating heart of the Tenderloin, I turned right on Turk and parked 10 feet from the corner.

After locking the car, I walked west toward Taylor. Almost immediately, I came upon five or six bedraggled older men standing or sitting on the sidewalk—one of them huddled in a doorway, bending over to light a crack pipe. Just a few feet further along sat another disheveled group—a man sucking on a pipe, a woman slugging a can of malt liquor. They paid no attention to me. A figure lay sprawled in a doorway, out cold. The acrid tang of urine hung in the air. I turned left on Taylor, walked the short block to Market Street, and turned left, passing the refurbished Warfield Building, the new home of Spotify and Benchmark Capital, conjoined to the old Warfield Theater. Midblock, a dozen young men were gathered around two street dice games, wads of money in their hands. A guy near the corner of Mason called out to me, “Hey, Joe, want something to smoke tonight?”

For as long as I’ve lived in San Francisco—going on 43 years now—I’ve been fascinated by the Tenderloin. It is the strangest neighborhood in the metropolis—maybe the strangest on the planet. In the midst of one of the most affluent cities in the world, it is a 40-square-block island of poverty and squalor. Its streets teem with the people the Chamber of Commerce does not want you to see: the ragged, the mentally ill, the addicted, the paroled, the homeless. While all big cities have such denizens, they are usually scattered here and there—not clustered right next to the most valuable real estate in town. But the Tenderloin couldn’t be any more central. It’s encircled by money: to the east, Union Square; to the north, Nob Hill; to the west, Civic Center and the Van Ness corridor. From the glittering shops of Union Square, it’s only a few minutes’ walk to the crackheads, derelicts, and prostitutes at Turk and Mason. Make a wrong turn coming out of the Hilton Hotel, and in a few seconds you feel like you’re in the South Bronx—or Calcutta.

This is bizarre. For if there is one ironclad rule that governs cities, it’s that money and poor people don’t mix. Once money appears, poor people disappear. Most American cities used to have Tenderloin-like neighborhoods downtown, but in almost all cases, those neighborhoods have been gentrified out of existence. Take New York’s Bowery, a name synonymous with flophouses and alcoholic despair as recently as the 1990s. Today it gleams with luxury hotels, shops, galleries, and museums. Or Los Angeles’ downtown, long a skid row Siberia, now a bustling yuppie dreamscape. Similar changes have occurred in cities as disparate in size and disposition as Vancouver, London, San Diego, and Dallas.

By rights, the TL ought to be suffering the same fate. San Francisco, as we all know, is swimming in cash: Land is being grabbed, leases are being quadruple-bid, high-rises are rising. And nowhere is this more apparent than in the booming construction zone on Market Street between Fifth and Tenth streets. This perennial no-man’s-land on the Tenderloin’s southern border, which was dominated for decades by check-cashing joints, strip clubs, cheap clothing and electronics stores, head shops, and boarded-up storefronts, is undergoing its greatest transformation since BART was built in the 1960s.

By offering businesses a six-year payroll tax exemption on new employees, San Francisco has enticed more than a dozen of them, including hot tech companies like Zendesk, Zoosk, Yammer, and IPO-bound Twitter, to move to the area. Twitter took over the splendid art deco Furniture Mart building at Ninth and Market for its 1,500 employees, revamping it with a roof garden, a state-of-the-art cafeteria, five snack kitchens, a game room, and a yoga-and-pilates studio. A 22,000-square-foot full-service grocery store is scheduled to open on the ground floor, the first bona fide supermarket in the area since the legendary Crystal Palace Market closed in 1959. Many other high-end real estate projects—some of them detailed in “Cranespotting”—are scheduled or under way nearby.

Under normal circumstances, in a normal city, the development of mid-Market would spell the beginning of the end for its neighbor, the gritty, feral Tenderloin. Developers would start buying up property, businesses would move in, fancy apartments and condos would replace decrepit housing stock, residential hotels would convert to tourist hotels, nonprofits would be forced out by rising rents, the police would crack down on street vice, and that would be that. In a few years, the Tenderloin would look like a dense, downtown version of Valencia Street.

But circumstances in the Tenderloin are not normal. And San Francisco is not a normal city. Barring a seismic shift in city politics, the TL is not going to gentrify the way that similar neighborhoods have in other cities. Not next year. Not in five years. Maybe never. For better or worse, it will likely remain a sanctuary for the poor, the vulnerable, and the damaged—and the violence and disorder that inevitably comes with them. The thousands of working people, seniors, and families, including many Southeast Asians, who make up a silent two-thirds majority of the Tenderloin’s 30,000 residents will remain there. And so will the thousands of not-so-silent mentally ill people, addicts, drunks, and ex-cons who share the streets with them—as well as the predators who come in from the outside to exploit them. The Tenderloin will remain the great anomaly of neighborhoods: a source of stubborn pride for San Francisco, or an acute embarrassment—or both.

Page two: What's preventing the Tenderloin from going the route of the Bowery?