At Modern Luxury, connection and community define who we are. We use cookies to improve the Modern Luxury experience - to personalize content and ads, to provide social media features and to analyze our traffic. We also may share information about your use of our site with our social media, advertising and analytics partners. We take your privacy seriously and want you to be aware that we have recently made changes to our Privacy Policy, which can be found here.


Arise, Tenderloin

Gary Kamiya | October 26, 2013 | Story Neighborhoods

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?

What’s preventing the Tenderloin from going the route of the Bowery or downtown L.A.? Four factors, taken together, make it virtually impossible for the district to gentrify in the traditional sense: zoning laws, city politics, entrenched nonprofits, and unique housing stock. Of these, longtime observers say, the housing stock is the crucial element. If the Tenderloin had different types of buildings, the almighty dollar might eventually trump the other three factors. But it doesn’t have different buildings. It has SROs.

The Tenderloin contains about 100 SROs, or single-room-occupancy residential hotels—more than any other neighborhood in the country. To find out how that came to be, I turn to Peter Field, a former mental health case worker in the Tenderloin with an encyclopedic knowledge of the neighborhood’s history. “These buildings were all erected after the great earthquake and fire of 1906 destroyed the old Tenderloin,” Field tells me during a six-hour neighborhood tour that covers about six blocks. (Field gives extraordinary public walking tours of the neighborhood twice a year through City Guides.) Older wooden buildings were replaced by taller structures made of reinforced concrete masonry. Many of them were SROs, built to maximize profits and cater to San Francisco’s large population of seasonal and maritime laborers. After World War I, the emphasis shifted to building studio apartment buildings, again to maximize profits. (So many businessmen and politicians used these studios to house their paramours that they were known as “mistress apartments.”)

For a time, the Tenderloin was what Field calls “San Francisco’s premier entertainment and vice district,” a hedonistic scene filled with nightclubs, theaters, brothels, and restaurants. Its SROs lacked kitchens and often individual bathrooms, but they were cheap and decently maintained. For decades, they housed many of the city’s working men and women: police officers, barbers, stenographers, teachers, factory workers. During the Great Depression, though, the Tenderloin began to decline. Its gradual deterioration accelerated in the 1960s and ’70s, when its aging, increasingly poor population was flooded with mentally ill patients who had been deinstitutionalized and prisoners released from overcrowded jails. They were joined by working-class African Americans displaced by urban renewal policies south of Market and in the Western Addition. In the Reagan years, the TL became increasingly populated by members of the urban underclass, many of them black, most receiving welfare, some of them homeless.

But the event that truly created the Tenderloin of today took place in 1980, when developers proposed three luxury high-rise hotels in the neighborhood. Residents and nonprofit advocacy groups organized to keep the big hotels out. The high rises were built, but in the aftermath of the fight, the city passed two crucial laws. First, the city made it illegal for owners to convert SROs into tourist hotels unless they also replaced the low-income units or paid into a fund for affordable housing. Second, it passed a zoning law lowering the height maximum in the Tenderloin from 30 stories to between 8 and 13.

These laws made it virtually impossible for developers to “Manhattanize” the Tenderloin. Meanwhile, the nonprofits, which had lobbied for the laws and led the fight to keep out the big hotels, themselves began to buy or lease buildings. These nonprofits, which include the Tenderloin Neighborhood Development Corporation (TNDC), the Tenderloin Housing Clinic (THC), and Mercy Housing, now own or lease more than 5,000 housing units in the Tenderloin. The city plays a critical role too: It has loaned the nonprofits money to acquire or rehab about 50 properties with 4,000 affordable units, and it holds or finances master leases on dozens of other such buildings. “The Tenderloin is the only place where the nonprofits own the housing,” says Field. “This protects the poor people in the neighborhood from changes in demographics.” It also gives the nonprofits a vested interest in keeping their clients from being dispersed.

Given this unique stew of interests, it’s easy to see why city politics stand in the way of any fundamental change in the Tenderloin. The mission of organizations like the TNDC, the THC, and long-established, widely respected charities like Glide and St. Anthony, is to provide support for low-income, vulnerable, and marginalized people, to protect renters from illegal evictions, and to defend their turf against gentrification. In progressive San Francisco, this is as close to a mom-and-apple-pie mission as you can find—and from the Feinstein administration in the late ’70s to Ed Lee’s today, San Francisco’s leaders have not only accepted the status quo; they’ve actively encouraged it.

“This is a well-run SRO,” says Del Seymour, leading the way into the Cadillac Hotel. Purchased in 1977 by the nonprofit Reality House West, the historic building provides 158 units of supportive housing. “Ninety percent of SROs, you can’t go in.” I ask him why not. “People selling crack in the buildings, having sex in the hallways, whoring—this is the Tenderloin!”

Seymour is a charismatic, blunt-talking former drug dealer, pimp, and addict who pulled himself together and now gives walking tours of what he calls “the other wine country.” He took me and some employees of a charity-run tech training program around the neighborhood, showing us sights both squalid and inspiring and talking about the need for change. Seymour doesn’t want a Giuliani-style cleanup, but he has no patience with his old brethren from the life. “If you’re shitting and pissing on yourself and whoring your sisters,” he announces, “you need to go.”

“I spent my nights in these SROs,” Seymour goes on. “I was not a good person. Selling drugs. I had 14 girls working for me.” What led to his downfall? “A business failure and a divorce.” How did he recover? “Jesus Christ,” he says. “And Marie and John Duggan of Original Joe’s. I owe everything to them. They gave me a job. She calls me every day.”

Seymour looks out past the faded woodwork in the Cadillac Hotel. “I can’t go back,” he says, meaning back to the life of hustling, despair, and addiction. “I don’t have a key to that door.”

Unfortunately, that door remains wide open for the countless unrehabilitated Del Seymours still prowling the TL. The people hanging out on the streets are a mishmash of small-fry dealers, hustlers, drunks, pimps, addicts, prostitutes, and the mentally ill, along with people who are simply there because they don’t want to stay cooped up in an SRO all day. Beat cops in the Tenderloin say that while their task is to protect the latter group from the criminals, it’s not always easy to distinguish between the two. And given that the police can’t arrest more than a fraction of the dealers, how can they make the streets inhospitable to the significant percentage of residents whose favorite pastime is loitering on the corner enjoying various petty vices?

Page three: Why didn't the police crackdown work?

The most obvious option for improving the quality of life of Tenderloin residents—intensive law enforcement—is also politically daunting. The city tried an aggressive enforcement approach in the Tenderloin in 2009, when then–police chief, now–district attorney George Gascón, shocked by what he saw during a walk through the Tenderloin, ordered his police to crack down on the neighborhood with the goal of making it unwelcoming to drug dealers and other bad actors. Two sweeps resulted in more than 500 arrests. But Gascón’s policy was criticized by Public Defender Jeff Adachi, whose office was inundated, and by the San Francisco Sheriff’s Department, which was forced to spend $500,000 to house new prisoners. Nor did Gascón’s effort draw significant support from TL residents: One manager of a community nonprofit told the Wall Street Journal that it was pointless to lock up dealers and addicts who were back on the streets days later.

But the real reason that the policy was soon abandoned is that it was simply unsustainable, for reasons made clear by Captain Jason Cherniss, commanding officer of the Tenderloin Police Station. Cherniss, who succeeded the legendary Joe Garrity this year, is one of an impressive new breed of police: book smart and street smart, tough and compassionate. “Arresting drug dealers is not the most effective solution to the Tenderloin’s problems,” he says. “They’re going to go away and come back.” He notes that most of the drug dealers in the Tenderloin come in from the outside—primarily from Oakland, Richmond, and Vallejo, and to a lesser extent from areas within the city—and that the neighborhood’s proximity to two BART stations, Powell Street and Civic Center, provides them with something that all Bay Area residents long for: an easy commute to work. “When BART was shut down [by a strike in July], you couldn’t get a crack rock in the Tenderloin,” Seymour attests. Like a vulture to carrion, trouble has a way of finding the Tenderloin. Despite being by far the smallest of San Francisco’s 10 police districts, it has among the highest rates of robberies and aggravated assaults in the city. As of August 31 of this year, there had been 270 cases of the former and 285 of the latter. By contrast, the far larger Richmond district had only 101 robberies and 79 aggravated assaults during the same time frame. According to Lieutenant Carl Fabbri of the Tenderloin Police Station, petty and midlevel drug dealing is so prevalent that the police are powerless to do more than arrest the most egregious offenders. “We could arrest drug dealers 24 hours a day,” he says.

A major police crackdown on street vice in the TL would require not only an enormous allocation of resources, but also a political commitment from the city that simply does not exist. “I only have so much staffing,” says Cherniss. “Every time I take a dealer off the street, I’m taking a cop off the street for an hour and a half, or longer. There’s a cost. If I hit Turk Street, then Hyde and Leavenworth get neglected. I have to be very surgical in how I do enforcement.”

To explain the unique policing challenge posed by the Tenderloin, Cherniss cites an analytical framework used by criminologists: the so-called crime triangle, which posits that crimes have three components—suspect, location, and victim. In the Tenderloin, “going after the suspects is pointless,” he says. “I need to get rid of the location to solve the problem.”

But how do you get rid of the location? The absolutist “solution”—relocating a good-size chunk of the neighborhood’s poor and marginalized people, as well as the organizations that support them—is not viable and never will be. Not in a city still haunted by a long and dishonorable tradition of either trying to warehouse undesirable populations on the outskirts of town (as when the city attempted to move Chinatown to Hunters Point after the 1906 catastrophe), or simply making them go away (as when it razed the Western Addition). But top-down measures are not the only way that cities change. They also change because of gentrification.

Undeniably, more middle-class people and businesses are moving into the Tenderloin and its surrounding areas. Art collectives like Hella More Funner at Taylor and Ellis have popped up. The Center for New Music recently opened at 55 Taylor, and the Cutting Ball Theater has brought live theater south of Geary Street again. A swanky new residential development, the Lofts at Seven, just opened in the old KGO building on Golden Gate, leasing studios and loft apartments for $1,875 to $3,000. And a big brew pub called Phantom Coast is slated to open on the southwest corner of Turk and Taylor—a notoriously gritty intersection that Seymour calls Tenderloin Ground Zero.

Many activists, politicians, and advocates for the poor view these developments with ambivalence. They welcome the improvements that the newcomers will bring to the street, but they worry that rising rents could drive poor people and nonprofit organizations out of downtown.

District Six supervisor Jane Kim says that she’s skeptical about the idea of trying to turn the Tenderloin into a mixed-income neighborhood. “I’d like to see a model of it working without displacing the low-income residents,” she says. “I haven’t seen that anywhere.” Citing her work as a community organizer in Chinatown, she adds, “The demographics of Chinatown and the Tenderloin are very similar in many ways. And Chinatown is not a mixed-income neighborhood; it’s a predominantly low-income neighborhood. I’d rather move the Tenderloin into the Chinatown model. Keep it low-income.”

Kim favors working with the neighborhood’s existing residents and businesses to improve conditions. She is trying to reduce the number of liquor stores (there are allegedly 72 within the 40 square blocks), improve lighting, convince markets to carry fresh produce as well as junk food and booze, and persuade the TL’s many working families to become more involved in the community. In addition to the thousands of chronically impoverished tenants in the neighborhood, some of whom pay only $200 a month in rent, there are many working people who pay $850 to $1,000 for subsidized studios and one-bedrooms. “I would also highlight that this is a wonderful neighborhood,” Kim says. “Some of the warmest, most generous people I’ve ever met are in the Tenderloin.”

Page four: The stakeholders scenario

Donald Falk, executive director of the nonprofit TNDC (among the neighborhood’s largest landowners), says that his organization is already feeling the pressures of gentrification. “It hasn’t felt like this since the late 1970s and early 1980s, when we started out with the battle against the big hotels. Rising property values are driving rents up. We’re going to see the Tenderloin become less affordable.”

Asked if there is an upside to the new money, Falk says, “It’s a conundrum. Lots of us would like to see more middle-class people, but would also like to see the neighborhood more affordable.” He bristles at the idea that newcomers might provide some kind of moral uplift. “I don’t like the idea that middle-class people will be role models for low-income people. In many ways, the low-income people should be role models for middle-class people.”

If Falk is worried about gentrification, THC cofounder Randy Shaw dismisses the possibility out of hand. Shaw, whose nonprofit led the fight to protect low-income SRO dwellers from abusive slumlords and now provides over 1,600 units of permanent supportive housing, has long been the most ardent and vocal defender of the Tenderloin—a kind of one-man neighborhood chamber of commerce. (He opens our conversation by reading me the riot act for writing in unflattering terms about the TL in my recent book, Cool Gray City of Love.) “It is impossible for the Tenderloin ever to be gentrified,” Shaw says flatly. His reason: the housing stock. “The gentry don’t want to live in places without kitchens or bathrooms.”

Even if the ordinance against converting SROs to tourist hotels were overturned, even if the nonprofits lost their leases and private developers bought up dozens of buildings, the cost of renovating those buildings and making them attractive to middle-class families would be prohibitive. And what developer would take that risk, with hundreds of lost souls still wandering the streets at all hours? Shaw also points out that opportunities for commercial development in the TL are severely limited by the neighborhood ban on commercial use in buildings above the second floor, the relative paucity of commercial spaces, and their small square footage.

"I’ve been involved in trying to get new restaurants to come into the neighborhood for a long time, but investors are not confident,” Shaw says. “There are successful bars here: There’s the new beer bar [Mikkeller] at 34 Mason. One of the most popular bars in the city is Bourbon & Branch at Jones and O’Farrell. But we’ve had a really hard time getting restaurants to open here, at least outside of Little Saigon. Investors are skittish.”

One might argue that this reluctance is largely due to the ongoing presence of the very population that Shaw has been vociferously defending for decades. But Shaw doesn’t accept the connection; instead he blames the city for not cracking down on notoriously squalid blocks like Turk between Mason and Taylor. “The first block of Turk is intolerable,” he says. “No resident anywhere should have to put up with that. We’ve been complaining about that forever. People like to blame the Tenderloin for the institutional failures of the city.”

Might there be another way, a way in which the Tenderloin could rise without losing its soul? A way that doesn’t require the mass removal of the indigent, or the heavy hand of the cops, or the ruthless class cleansing of gentrification?

A blue-sky vision that’s quietly being floated by city officials, nonprofit leaders, and police staff—let’s call it the involved stakeholders scenario— could provide just that. The scenario pictures new businesses continuing to trickle into the neighborhood, along with increasing numbers of young professionals drawn by its central location and relatively low rents. (Market-rate studios and one-bedrooms in the TL typically rent for $1,200 to $1,800—not cheap, but well below the going rate in most San Francisco neighborhoods.) The key to the scenario is that these newcomers, rather than demanding that the police alone solve the neighborhood’s problems, shoulder a lot of that burden themselves. They keep their properties clean and well-maintained. If someone urinates on their storefront, they go out with a bucket of bleach and water and deal with the mess. They strike up conversation with the people congregating in front of their apartment. The new stakeholders work closely with the nonprofits, with law-abiding members of the TL community, and with the police.

The scenario plays out slowly and fitfully, but it works. The word goes out on the street that the TL is no longer an anything-goes zone. You can maybe drink a little malt liquor or smoke a joint on the corner (they do that in Noe Valley), but coke, crank, crack, and smack are out. Deal drugs and you’re going down hard. And you can’t use the streets as a toilet.

Over time, the theory goes, most people accept the new rules. Those who are too damaged or violent to get with the program are locked up or shipped away to treatment centers in other areas. Gradually, the worst corners—Turk and Mason, Turk and Taylor, Ellis and Jones—are cleaned up. This brings in more middle-class people and businesses. In the end, the scenario posits, the neighborhood stabilizes into a functioning crazy quilt: a block-to-block, building-to-building patchwork of wealth and poverty, blacks and whites, Asians and Latinos, SROs next to renovated apartments, supportive housing beside new condos. It isn’t Pacific Heights. It has its problems. But it’s a productive, vibrant neighborhood in the heart of San Francisco.

If the city could pull this off, it would have achieved something almost miraculous: a neighborhood offering all the benefits of gentrification (no feces on the street, safety for kids and seniors, thriving cultural institutions, affordable restaurants, good grocery stores, a dynamic street life) without any of its drawbacks (displacement of residents, skyrocketing rents, and loss of ethnic and economic diversity). For middle-class San Franciscans weary of watching themselves being priced out of neighborhood after neighborhood, this achievement would create a pinnacle of urban living. It would be the city’s finest hour. And it would only be possible in the Tenderloin.

Is this anything more than a utopian pipe dream? When I ask the TNDC’s Falk that question, he is more optimistic than I expect. “It’s not just viable; it’s our vision,” he says. “And in some ways, the work we’ve done in the last 30 years has made that scenario possible.”

Page five: “If gentrification means you take care of the neighborhood better and don’t displace the people in the SROs, it’s OK.”

Captain Cherniss, too, is convinced that an influx of responsible stakeholders would brighten the Tenderloin’s future. “I expect to see positive changes here,” he says. “There are a lot of great, committed people coming in who understand that a key part of improving the neighborhood rests with them. They’re extending their sphere of responsibility, not just locking their doors.” He cites the TNDC, the THC, and other nonprofits as role models. “They’re our partners,” he says. “They improved the SROs. They’re in close contact with us about what’s happening on the street. To me, they’re doing as much for public safety as me, or more.”

For its part, the city is hoping that economic development and a revitalized community will turn the Tenderloin around. Amy Cohen, director of neighborhood business development at the Office of Economic and Workforce Development, cites the success of the city’s work in mid-Market and its plan to apply what it learned there to the Tenderloin. “We recognize that creating a vibrant, healthy, mixed-income neighborhood in the TL will be challenging,” Cohen writes in an email. “A growing number of people, from Tenderloin residents themselves to new tech companies to art groups, share this vision and are working in various ways to make it happen. It will not happen overnight, but there is more potential now than in decades.”

Whether this future is possible is anyone’s guess. Many obstacles stand in the way. What if the users and pushers on the street don’t leave the neighborhood, but just keep popping up in new locations in an endless game of Whac-a-Mole? How will the police sort out the dealers from the users and the users from the loiterers? If pressure from middle-class residents builds for the police to really crack down and clean up the streets, will progressives charge that they’re criminalizing poverty?

History does not inspire confidence. As Supervisor Kim points out, there are few if any models for this mixed-income success story. But if the TL is going to become a safer, saner place, people like Del Seymour and Tiffany Apczynski, who represent the neighborhood’s proud old guard and idealistic new guard, respectively, are going to play a crucial role.

Apczynski is the director of social responsibility for Zendesk, the first of the tech companies to migrate into mid-Market. In order to qualify for the so-called Twitter tax break, Zendesk agreed to submit a community benefits agreement (CBA) that commits it to devoting time and resources to working with the Tenderloin and mid-Market communities. Apczynski drafted the district’s first CBA and has overseen Zendesk’s involvement with community gardens, local caterers, and the Tenderloin Technology Lab, a training program run by the nonprofit St. Anthony Foundation.

Mandated “give back to the community” programs like Zendesk’s have been criticized as PC Band-Aids, and both the Central City Extra newspaper and the website Buzzfeed have raised questions about the efficacy and enforceability of the CBAs. But Zendesk has won praise from Tenderloin activists for the depth of its commitment to the neighborhood. Regular teams of company volunteers serve meals at Glide and cook breakfast at the Gubbio Project, a unique program at St. Boniface Parish that allows people to sleep on its pews between 6 a.m. and 3 p.m. (The Gubbio Project deserves special mention. Seymour took me and a half dozen Tech Lab employees into St. Boniface one morning. It’s a regular part of his walking tour. Inside the beautiful old church, 80 or 90 people were sleeping—old Asian ladies, children, scruffy people who looked down on their luck, even a couple of young Euro-looking travelers with backpacks. Most of them were lying on the pews, a few in the aisles. The smell of incense filled the air. It was silent and warm, a refuge. The figure of Christ looked down from behind the altar. I am not a religious person, but I found my eyes blinded with tears.)

Apczynski has no illusions that companies like hers possess the key to fixing the Tenderloin, but she’s game to try. “Is it all puppies and rainbows? No. It’s a tough neighborhood,” she says. “But most people in tech want to humanize technology, to do something bigger than themselves. Why can’t we use the kind of innovation we use in our work life to change the city, to help the neighborhood?”

For Seymour, the influx of broad-minded young techies like the Zendesk employees represents less a threat than a source of hope. “I don’t think there’s anything wrong with gentrification if it’s done well,” he says as we amble through a TNDC-run community garden across the street from the Asian Art Museum. “If gentrification means you take care of the neighborhood better and don’t displace the people in the SROs, it’s OK.” In any case, he prefers the geeky tech crowd to the stuffier suit-and-tie set. “The young people coming in now,” he says, “are tolerant of the Tenderloin lifestyle.”

After dropping my daughter off at Hotel Nikko on that warm September night, I rambled around the Tenderloin. I went into three different privately run SROs and asked to see their rooms. For $60 a night or $1,000 a month, I could get a nightmarish cell with an air-shaft window and a filthy bedspread. As I stood outside one establishment, a crazy-looking, muscular man with a timid companion came up behind me and spat, “Get out of the way of the door.”

I walked back to Turk and Taylor and entered the 21 Club, on the corner. Eight or ten people were there, mostly older men—I recognized two or three of them from earlier visits. Frank, the joint’s amiable, indomitable bartender, with his trademark cap, was laughing with one of the regulars. As a tune came on the jukebox, an old guy in a threadbare suit with a fixed, slightly foreboding expression got off his barstool and stood there, his hands at his sides, looking off into space. I wasn’t quite sure what he was doing. “That’s Eric Clapton,” he announced to his pal on the next barstool. “That’s a Les Paul.” I realized that this gloomy-looking old man was playing the world’s most unobtrusive air guitar.

There was a stir in the tiny bar, and I turned to see the entrance of a beaming, attractive, middle-aged woman with a short, white Afro and a weathered-looking, long-haired guy wearing shorts and a white tank top. Everyone was congratulating them—they had just gotten married. One of the men I’d recognized came over and tried to buy them a drink, but the new bride smilingly said that she’d have to take a rain check because she was tired and wanted to go home. After chatting for a few minutes, the couple waved to everyone and left.

I hung out for a little while longer, half listening to the old friends talking at the bar. The atmosphere brought to mind a den in a worn-out alternate universe, filled with family members as kindly and as threadbare as old stuffed animals.

Leaving the 21 Club, I crossed Taylor and walked down the south side of Turk. Three or four people had set up a barbecue on the sidewalk. “You want some barbecue?” inquired a friendly woman standing next to the smoking grill. “How much is it?” I asked. “Well, the ribs are $7 and the chicken is $5. You hungry?” “Maybe later,” I replied. “Smells good.” “All right, well, you come back here, Mr. Tommy Bahama,” she said.

I wandered on down the street. On Jones, a figure lay sprawled in a doorway. A block later, I saw a hypodermic syringe glittering in the gutter.

Gary Kamiya is the author of Cool Gray City of Love: 49 Views of San Francisco and, beginning this month, the Executive Editor of San Francisco.

Originally published in the November issue of San Francisco

Have feedback? Email us at
Email Gary Kamiya at
Follow us on Twitter @sanfranmag


Photography by: