San Francisco still has a seedy heart

San Francisco's Tenderloin is gritty, gross and maybe a little sexy. How does it survive?

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San Francisco still has a seedy heart
Excerpted from Cool Gray City of Love

This book begins and ends with walking. Its spirit is ambulatory — the product of the countless explorations I have made across San Francisco on foot. I began those wanderings more than 40 years ago, but only in the past two years have they assumed the obsessive form that has led my friends to hide when I come calling, chirpily announcing another thrill-packed excursion to the Outer Mission.

Blame it on titanium. For most of the last two decades, my knees were so shot that I could not walk without pain. You learn to work around chronic pain, but you lose certain things you are not even aware of. One of them is whims. A whim-less city is a diminished city, a city whose mysteries are kept under lock and key, a city that repeats itself like a scratched record. After I had my knees replaced, San Francisco became endless and enticing. Like an iron-jointed butterfly, I began flitting around town – at first aimlessly, then systematically. And so it was that one fall day, after dropping off my daughter at her high school a block from that endearingly city-soaked rectangle of green called the Panhandle, I decided to finally learn Golden Gate Park.

I should have known the great park better. I’d been going there forever. But every time I got off the beaten trail I got lost. The problem was that I’d never tried to learn it in a systematic way. Golden Gate Park is so big — at 1,017 acres, it’s 20 percent larger than Central Park, and much more overgrown and opaque — that if you don’t approach it logically, you’ll just keep forgetting whatever you learned. So I divided it up into rough grids and started exploring.

It took about 20 days, walking an hour or two a day with my dog, to cover just about every part of the park. It was glorious and addictive, making new discoveries every day. I savored the mingled pleasure of the mapmaker and the outlaw. I was Tom Sawyer and Huck Finn — one part of me greedily storing up information, the other blissfully absorbing experiences that had not yet blazed trails through the forest of my neurons. It turned out that systematic flitting, if not the secret to human happiness, is a pretty good start.

My park voyage turned out to be a dry run, an experiment on a bite-sized, miniature version of San Francisco. For I had so much fun that when I was done, I decided to do the same thing with the rest of the city. I set out to “do the Knowledge” for San Francisco.



“Doing the Knowledge” is an expression used by London taxi drivers. To get a license, hacks must learn every single street in that vast metropolis — and as anyone who has ever looked at the endless map-book “London A to Z” knows, that is a feat that would tax even Funes the Memorious, the character in the Borges story who never forgets anything. Preparing for the test is called “doing the Knowledge.”

I figured it wouldn’t be that hard. Compared to London, San Francisco is a one-horse town. Plus, I already had a head start, having been a taxi driver here for years. So I set out to do the Knowledge (walking and rolling version) for San Francisco – to explore as many hills, streets, inlets, trails, vacant lots and beaches as I could in the entire city. I left some out, for reasons of logistics, personal safety and utter boredom, but I was pretty thorough. If you divided the city into 1,000 approximately quarter-mile-square grids, I can honestly say I have set foot or bike tire on every one of them.

I undertook this somewhat demented odyssey, in part, to do research for what was to become this book – but only in part. I knew that very little of what I discovered would ever make it into print. I was not planning to write a guidebook, and even if I had been, it seemed highly doubtful that there would be a large market for a tome offering detailed instructions on how to slip between the two houses at the end of Valletta Court (was Thomas Pynchon involved in naming the SF streets?), skirt someone’s backyard, make your way through a dense thicket of blackberry bushes, push past a bush of bright yellow Bailey acacia, clamber over some dead trees, and climb up the craggy face of an obscure hill on O’Shaughnessy Hollow.

So what drove me to go on those countless 8 a.m. walks was not just a search for material I could use. It was the same impulse that drove me to master the park: Curiosity. Passion. The desire to discover the unknown. To make my little world bigger and deeper. Thoreau described it in his essay “Walking”: “An absolutely new prospect is a great happiness, and I can still get this any afternoon. Two or three hours’ walking will carry me to as strange a country as I expect ever to see.”

I can’t deny that there was a childish, game-like element to my quest. Like all games, it involved a kind of miniaturization, a shrinking of the world. To be interesting, my little universe had to have borders. I made the arbitrary decision that the 46 square miles bounded by Ocean Beach on the west, the waterfront on the north and east and Daly City on the south was sacred space. Everything inside those lines was interesting by definition.

“A man’s maturity consists of regaining the seriousness one had when a child at play,” Nietzsche wrote. And it was child’s play for me, the whole peculiar odyssey. It was my version of “Blind Travel,” the game played by Hugh Lofting’s Dr. Dolittle. When the good doctor wanted to go on a voyage but wasn’t sure where to go, he closed his eyes, opened his atlas to a random page, and made a mark with a pencil: Wherever the pencil landed, he had to go. My world atlas was a tattered old Thomas Brothers map of San Francisco, and I didn’t choose my spots quite that blindly, but the selection process was similar. It was almost absurd how euphoric I felt as I tramped merrily through remote parks, across hidden trails and through vacant lots, planting my little invisible flags like some two-bit Cabrillo. Best of all, I realized that I could play this game forever. If I went to a different place in the city every day, at the end of a year I could start again and it would all feel new – an urban explorer’s version of Kierkegaard’s “rotation method.” I felt so giddy I began to be a little embarrassed. This was not grown-up behavior. John Calvin did not wander the streets of Geneva with a blissed-out grin on his face.

I was starting to write myself off as one of those inexplicably beaming homeless kooks you see stumbling down Market Street when I remembered an explorer who was even happier than me: John Muir. The legendary naturalist walked into the Sierra Nevada one day, and that was it. He was permanently stoned on some kind of divine speedball ever after.

I had found my role model. If stumbling around in a happy daze was good enough for John Muir, it was good enough for me. I never tried to wipe the smile off my face again.

Actually, I needn’t have worried about being too euphoric. Life being what it is, the smile tended to vanish of its own accord. On all too many days, San Francisco became just a dull backdrop to my duller mind.

On those days, I sometimes found it useful to remind myself of what happened to the Spanish after they discovered California in 1542. For more than two hundred years after that, as their explorers sailed up and down the coast, they kept missing that narrow, fog-shrouded break in the coastal mountains we now call the Golden Gate.

That story is a parable that applies to all of us, whether we live in San Francisco or Sheffield, Perugia or Paris, New York or New Delhi. The real treasures are right under our noses.

This book is a voyage to a beautiful land I discovered long ago. And one that I am seeing for the first time today.

In the universe of San Francisco, the Tenderloin is the black hole, the six-block-by-six-block area where the city’s urban matter is most intensely concentrated. It is the only part of San Francisco that remains untamed, its last human wilderness. Without the Tenderloin and its radioactive core of junkies, drunks, transvestites, dealers, thugs, madmen, hustlers, derelicts, prostitutes and lowlifes, this smug, overpriced, increasingly homogenous burg would feel like one of those motel bathrooms that are “sani-sealed for your protection.”

The Tenderloin is the creepy Mr. Hyde (which happens to be a street running through it) to the rest of San Francisco’s respectable Dr. Jekyll (who, appropriately, goes unhonored – although some jokester named a hotel on Hyde “The Jekyll”). And this evil twin isn’t hidden away in some asylum on the outskirts of town. The Tenderloin is surrounded by Union Square, Nob Hill, the Civic Center and the gentrifying mid-Market district. It’s about as central as you can get.

This is weird. Many cities used to have “bad” neighborhoods in the heart of downtown, zones of misrule where the primal human urges – to get laid, to get high, and to get money – were allowed to bloom furtively in the night. But most of them are gone now, victims of gentrification. New York’s Times Square feels like Disneyland, Vancouver’s Gastown has been tamed, Boston’s Combat Zone was rendered hors de combat years ago. And of those that remain, none take up 36 square blocks of prime real estate in the middle of one of the most expensive cities in the world.

Union Square is the center of San Francisco’s downtown, the quintessential public space of Any Corporate City, 2012. An invisible capitalist force-field (in the beginning was the Logo, and the Logo was with God, and the Logo was God) emanates down from the huge airline-and Midori-touting billboards looming over it. But you only have to walk a couple of blocks from the square’s bustling southwest corner at Geary and Powell to find yourself in a lurid demimonde populated by characters out of a Denis Johnson novel.

All of which is to say that the Tenderloin is a large turd – often a literal one – floating in the crystal punchbowl that is San Francisco. So why is it still here?

Because the city wants it to be here.

For decades, the Tenderloin has been carefully protected by the city and various non-profit organizations. It’s not that these officials, social workers, homeless advocates and low-cost housing activists want to maintain a zone of misrule, crime and filth in the heart of the city: it’s simply an inescapable consequence of their laudable commitment to defend society’s most vulnerable members. The problem is that by saving the baby, you also save the bathwater. No one has figured out a way to protect the “deserving poor,” to use the condescending 19th century parlance, without also protecting the creepy, kooky and dangerous poor. The result is, in effect, a protected urban wildlife zone, a Bottle City of Squalor.

But the Tenderloin is more than that. It is also a memorial to a rich and vanished era – what geographer Richard Walker has called “the high tide of dense urbanism.” For it was here, in the neighborhood’s unique collection of single-room occupancy (SRO) hotels and apartment houses, that the great army that once made up the blood and guts and sinew of American cities lived. Tens of thousands of clerks and salesmen and stenographers and hobos and longshoremen and cops and dressmakers and carpenters and factory workers inhabited these cheap but decent rooming houses. Most of them were single. Many of them were women. They were drawn to the city because they could find work here. As Paul Groth notes in “Living Downtown: The History of Residential Hotels in the United States,” for these newcomers, these inexpensive rooming houses offered freedom, anonymity, sexual liberation – all in the heart of the city.

What is remarkable about the Tenderloin is that it has remained physically unchanged for more than 80 years. It is a time capsule. The same progressive forces that have kept out “progress,” and inadvertently created a Museum of Depravity, have also created a Museum of the Lost City, a vanished world memorialized in the neighborhood’s extraordinary collection of residential hotels. There are hundreds of these historic SROs in the Tenderloin, the largest number in the world. The SROs are the reason that in 2008 the Uptown Tenderloin was placed on the National Register of Historic Places, the 24th San Francisco neighborhood to be so listed. All of these three-to-seven story brick and masonry buildings were built between 1906 and the Great Depression. Almost all of them are essentially unchanged, right down to their blade signs. These once-elegant buildings have fallen on very hard times, but they still conjure up the romance and mystery of the Naked City, with its eight million stories. They are the ultimate urban hives.

In an uncanny way, the Museum of Depravity helps bring the Museum of the Lost City to life. If all those rooming houses were occupied by employees of Twitter – and that day may be coming – the ghostly romance of the Tenderloin’s past would not feel quite as rich and strange.

The very first time I set foot in the Tenderloin was when I was a 17-year-old student at Berkeley High. I went with my friend Ben, a black guy who smoked Kools and read Husserl, over to the big city from Berkeley to hook up with a pal of his for some reason I have forgotten. We went into an old apartment building, took the elevator up and walked into a studio apartment that looked out over downtown. It was the first time I had ever been in An Apartment. I dimly remember that it was airy and spacious – there are a lot of beautiful rooms in those old buildings – but my memory is somewhat cloudy because his friend pulled out a water pipe (another first) and we proceeded to get stoned. This was an appropriate introduction to the Tenderloin: a longhaired half-Japanese dude and two black guys interrupting their vague urban mission to puff away on a water pipe (unless that was the mission). The die was cast: Most of my subsequent experiences in the Tenderloin have involved some kind of sin.

I got to know the Tenderloin during the seven years I was a taxi driver in San Francisco. Sin and taxi driving go together like gin and tonic, and the Tenderloin was the smudged highball glass where they mixed. The ’Loin was ground zero for sex, the sub-basement of the lower chakras. Sex radiated out of its innumerable windows and filthy sidewalks, from Frenchy’s K&T Bookstore (the name “Frenchy” a subtle tipoff as to the types of books it carried) to the gaudy, teetering whores on Geary Street, from the bottom-of-the-barrel all-night Mini-Adult Theater on the lunar corner of Golden Gate and Jones (admission $2, no charge for an attempted blow job by the drunken homeless guy who just sat down next to you) to the scary Last Exit to Brooklyn drag queens on Larkin, from the gay male hustlers hanging outside the Peter Pan bar at Market and Mason (an intersection delicately known as “the Meat Rack”) to Jim and Artie Mitchell’s upscale flesh joint on O’Farrell Street.

There was a major cross-dressing and transgender scene in the TL, catered to by unnerving bars like the Black Rose. One night about 2 a.m. I picked up a 30-ish straight man on O’Farrell. He was pretty drunk. He was a nice guy who seemed completely freaked out. He started babbling as soon as he sat down. “Oh my God,” he said, “the weirdest thing just happened to me. I picked up this girl and she turned out not to be a girl.” He had gone drunkenly through with the sexual encounter anyway and now he needed to exorcise the whole bizarre incident. I tried to reassure him that he would be OK, but he was as jangled and jumpy as if he had just poured ten cups of espresso into his id.

The Tenderloin was the head and sharp teeth of the sexual octopus, but its clammy tentacles reached into every corner of town, from Pacific Heights to Miraloma Park to the Ingleside. You had to be a taxi driver to feel it. Sometimes every fare of the night seemed to have something to do with sex. I once picked up an ordinary-looking housewife in a deeply boring house in the deep Sunset who told me she was on her way to meet a client/friend with who she’d been having a once-a-week, mutually beneficial rendezvous for years. As I drove through the streets at night, the radio crackling with the dispatcher calling out intersections, I sometimes had the impression that the entire city was an enormous, intricate machine powered entirely by sex.

The Tenderloin was often involved in these libidinous journeys, either as a starting point or a destination. Out-of-town businessmen looking for action would get in my cab and nervously check me out before asking me if I knew where they could, you know, have some fun. Out of consideration for my fares’ sensitive feelings, I downplayed my nice college boy demeanor, putting on a Damon Runyonesque “how ya doin’, pally” rap to put them at their ease. Two Japanese salarymen once asked me to take them to something that sounded like “hlibod sho.” I had no idea what they were talking about. They had to repeat it twice until I realized they were saying “ribald show.” I felt like calling up the editors of the OED and reporting the first conversational use of the word “ribald” since 1911. I took them to the Mitchell Brothers.

Say what you will about Japanese businessmen, they are not self-conscious about sex. Indeed, for some of them, it appeared that having a naked woman shove her ass in their faces was a tourist activity to be checked off the to-do list, on a par with visiting the Legion of Honor or Golden Gate Park. During a visit to a slightly sleazier fleshpot than the Mitchell Brothers, the New Century on Larkin if memory serves, I was surprised to suddenly hear a piercing whistle. I looked away from the gyrating woman on the pole to observe ten or 15 Japanese men getting up and moving methodically towards the exit, ready to get back on the tour bus. It was the finest display of organized horniness I’d ever seen.

A master of disorganized horniness, I fumbled or otherwise failed to take advantage of what few sexual opportunities came my way in the Tenderloin. Once I somehow ended up going with an older woman fare up to her room in the Mark Twain Hotel on Taylor. She was clearly ready for me to drop my nice college boy act and my pants, but I lost my nerve and all my fame and left without doing anything. I later found out that in 1949, Billie Holiday was busted for opium possession in room 203 of the Mark Twain, an event that may have somehow put a “Shining”-like curse on the proceedings.

I had slightly better luck, if that’s the word I want, with a lunatic stripper who worked at one of the ’Loin’s legendary strip clubs, the Chez Paree on Mason. The Chez Paree was famous for its neon sign of a long female leg, bent and ready to kick the can-can. I met this woman one day on the beach at Aquatic Park and took her the next day to Lake Anza in Berkeley. Unfortunately, her spectacular body turned out to be accompanied by a schizophrenic brain. We sat on our towels talking about this and that, when she suddenly and suspiciously asked me if I was gay. Apparently trying to make innocuous first-date conversation was a bad move. Later we did manage to get in a little groping in the back seat of my stepmom’s 1962 VW bug. It was pretty hot, but in the middle of it, she suddenly pulled a hairbrush out of her purse and began utilizing it in a way for which it was not designed. That would have been all right, in fact it would have been all right to an unparalleled degree, except for the fact that 1) it felt like she had suddenly gone into her Chez Paree routine and 2) I couldn’t convince her to come back to my apartment. When I dropped her off at her Tenderloin hovel, she told me to come by the Chez Paree after 2 a.m., when she got off work. I did and waited for half an hour, but the only person who came out was a large, violent-looking bouncer who told me to get lost. Hairbrush woman, in the extremely unlikely event that you are reading this, what did I do wrong?

In addition to being haunted by such crackpot Circes, the Tenderloin also featured — and still does — more than its share of young males whose approach to life is summed up by the line delivered by the blackmailing George Sanders character in Rebecca: “I’d like to have your advice on how to live comfortably without working hard.” Two of these worthies, one a tattooed white guy who had long hair of the non-hippy kind and one an ominous-looking Latino blood, hailed me on Taylor and Eddy one night. I was a fairly new driver and it was a slow night, so when they said they wanted to go to the airport, I agreed. Tilt! Taxi commandment number one: Do not pick up scary dudes in the Tenderloin who look like they just got out of the joint and say they want to go to the airport even though they have no luggage! Taxi commandment number two: If one of these scary dudes gets in the front seat and one gets in the back, directly behind you so you cannot observe the gun he is pulling out, immediately defecate in your pants, exit the vehicle, and run screaming down the street!

Unfortunately, I failed to follow either of these easy rules. Instead, I drove down Sixth Street and got on the freeway. After a minute or two, I felt the unpleasant sensation of a gun barrel pushing up against the back of my head. I was informed by the muscle-y San Jose speed freak white dude in the front seat that this was a stickup. They then made me drive around while they looked for a remote place. They got kind of chummy as we rolled along. Blood in the back seat said, “Hey, you drive pretty good. You ever think about a life of crime?” Laugh? I thought I’d die!

Finally they told me to exit at Colma and had me drive into the vast city of the dead, where Wyatt Earp is buried in a cemetery called Hills of Eternity. I did not like this at all. They told me to get out of the car. I jumped out and sprinted down the road, screaming “Help!” while waiting for the bullets to rip into my back. But the only sound was the engine roaring as they drove off at top speed.

The SF police soon came and picked me up. This turned out to be almost as scary an ordeal as the robbery and kidnapping, because as we headed back to the city they suddenly got a radio call about some heavy crime that had just gone down in the Geneva Towers, the scariest projects in town before they were blown up. They took off at 90 miles an hour towards Visitacion Valley. As we approached the terrifying highrises, the cop riding shotgun actually pulled out yes, a shotgun, and stuck it out the window. When the radio said the suspect was a black male, the driver sneered, “Oh, yeah, that’s a big fucking surprise.” They were total macho cowboys, but considering they were working the Geneva Towers beat during the crack-crazed 1980s, which would have to qualify as one of the worst jobs in the history of the world, I had to cut them a little slack. They finally dropped me off at the Yellow Cab lot. The next day the cab turned up hidden in an old railway cutting at the base of Potrero Hill, just a few blocks away.

My dubious experiences in the Tenderloin stood in a long and dishonorable tradition. “If you were to throw a ball a thousand feet into the air from here,” Peter Field told me as we stood on the corner of O’Farrell and Mason, “wherever it landed, the chances are it would hit a building that was once involved in some kind of illegal activity.”

Field probably knows more about the Tenderloin than anyone else. He is a social worker who worked in the neighborhood for 12 years and is obsessed with its history. He has spent hundreds of hours poring over City Directories and Sanborn insurance maps, the sources that allow sleuths to follow the convoluted trails of people and businesses through the vanished urban landscape. I came upon some pieces he’d written about the TL online and called him up. He gives a walking tour of the neighborhood twice a year through City Walks, a non-profit organization whose volunteer guides lead tours all over town. I had just missed his tour but he offered to take me around himself. His normal tour lasts about two and a half hours. We spent six and a half hours walking about six blocks.

I met Field at the dead center of San Francisco, the Powell Street turnaround at Eddy Street. It was a hot June Sunday and thousands of tourists and locals were swarming the streets. But they soon faded into the background as Field drew me into a lost world – of lonely merchant sailors in sad rooms, old people eating in white-tablecloth cafeterias, thousands of excited men on Ellis waiting for a boxer to emerge from a weigh-in, evil pimps drugging girls, French restaurants with discreet upstairs rooms, Miles Davis riffing with Wynton Kelly at the Blackhawk, military shore patrols and San Francisco’s finest scouring the streets together looking for AWOL sailors, homeless kids selling their bodies on the corner of Geary and Polk, hobos returning to the same shabby hotels for decades. By the end of the six hours, it felt like I had just watched a time-lapse film of the neighborhood’s entire long, rich life.

Like most of old San Francisco, Field said, the Tenderloin was a wasteland of sand dunes and scrub brush. Its first white inhabitant was a viticulturist named Henry Gerke, who in 1847 built a two-story building at Eddy and Mason (the streets did not yet exist), near a large spring-fed pond that stood where the Flood Building is today. The isolated area was known as St. Ann’s Valley. It was only three-fourths of a mile to the center of town, the old Spanish Plaza that had been renamed Portsmouth Square after the American conquest of California in 1846, but the dunes were so high and deep it was a long hike to get there. A saloon called St. Ann’s Rest opened in the 1850s, catering to travelers on their way to the Mission. But there were few inhabitants until 1860, when the Market Street railroad opened, its path cleared by the “steam paddies” – steam-powered excavating machines that were so named because they could supposedly do the work of 20 Irishmen. By 1866, the former wasteland was completely developed. It was a typical San Francisco neighborhood of homes and small businesses, with a few mansions scattered here and there.

The event most responsible for turning the Tenderloin into what Field called “San Francisco’s premier entertainment and vice district” took place in 1878, when an entrepreneur named “Lucky” Baldwin built the opulent Baldwin Hotel at Powell and Market. The first-class hostelry, which competed with the famous Palace Hotel a few blocks east, included a theater. Other theaters and music halls followed, along with office buildings. “This brought new customers into the neighborhood,” Field said. “Rich rancher Johnnies, rich town Johnnies, office workers.” Following the law of supply and demand, in 1884, the first parlor house – a genteel brothel – opened at 223 Ellis, presided over by Miss Ines Leonard of Virginia City. Others soon followed. By the 1890s, the Tenderloin had been transformed from a stolid middle-class neighborhood into a jumping district of theaters, hotels, parlor houses, restaurants (many of which doubled as brothels or places of assignation), and gambling joints.

As we spoke a young guy with a scar on his face and reeking heavily of alcohol lurched up to us. He wanted to know what we were talking about. When we wouldn’t tell him, he punished us by releasing a toxic cloud of Royal Gate Vodka fumes in our faces. “Hey!” he said. “Wait. Listen…The court said I was not allowed to own a pencil or anything to write with. Do you know why?” he asked. Receiving no answer, he stumbled off.

Sex was a prime Tenderloin draw, just as it was for San Francisco’s more famous red-light district, the Barbary Coast. But the two fleshpots were completely different, Field said. “The Tenderloin was more refined than the Barbary Coast. The Barbary Coast attracted sailors and some upper-class men going slumming. But the Tenderloin attracted all classes. You could go out to dinner, go to the theater, and then maybe stop in at a parlor house.” The semi-respectable nature of the neighborhood was solidified when it became the center of San Francisco’s fraternal society – the Odd Fellows, Masons, Elks and so on. “These societies would have their monthly or yearly meetings, and the men would want to have a good time,” Field said. “They’d wander around the neighborhood, go to the bars and parlor houses. The newspapers of the time are filled with stories about men who lost their fraternal diamond stickpins in the neighborhood.”

If the Tenderloin was not as sleazy as the Barbary Coast, it was still pretty sleazy, and there was ongoing tension between it and the merchants on the Union Square side – a battle that has continued to this day. After the great earthquake and fire of 1906 destroyed the Tenderloin, along with all of downtown San Francisco, there was lots of talk about “reclaiming” it. After the district was rebuilt, however, it resumed its Sodom-like ways – “maybe even more,” Field said. This is when it began to be referred to as the “uptown Tenderloin,” to distinguish it from its brief incarnation in the Fillmore District.

We walked up to the corner of Ellis and Powell. East on Ellis, where a parking lot now stands, was a saloon and betting parlor owned by Harry Corbett, the brother of “Gentleman Jim” Corbett, the former heavyweight champion of the world. “This was the center of betting parlors in San Francisco,” Field said. “Corbett became a boxing promoter and had his own set of scales on a Turkish rug. When you made it as a boxer, you weighed in on his scales. Ellis Street would be crowded with men waiting to get a look at their heroes. Men like Bob Fitzsimmons and Sailor Sharkey.” The joint was raided repeatedly by the police. After 1906, it was rebuilt as a French restaurant with private rooms upstairs – a San Francisco tradition. The purpose of these rooms was made clear by the discreet behavior of the waiters, who were trained not to enter the rooms unless summoned.

The great earthquake and fire of 1906 destroyed the Tenderloin, along with all of downtown San Francisco. The post-quake reconstruction was responsible for the Tenderloin’s unique architectural character. Its buildings had mostly been one or two story wooden houses and small hotels. The new buildings were higher, three to seven stories, made of brick or masonry, and had many more units, mostly studios. Into this densely-built-up, compact area, close to offices and factories and restaurants and bars, poured the 1920s and 1930s equivalent of the young people who today work as baristas or as retail clerks and live in the Mission District (or maybe, mutatis mutandis, those who work at the Home Depot and live in San Leandro) – clerks and salesmen and barbers and firemen. Starting in the 1920s, as Paul Groth notes, women began to move to the rooming houses in large numbers. (Until salaries for stenographers rose in the 1920s, women did not make enough money to be able to live alone.) For the sheltered young American men and women who found themselves bumping into each other in the hall on the way to the bathroom, the Tenderloin and similar cheap downtown neighborhoods offered the chance to break free of Victorian small-town sexual codes. As Groth points out, official America’s century-long war on SROs, which culminated in their mass destruction in the mid-1970s to the early 1990s, was driven in large part by a moralistic disapproval of their secular, individualistic ethos, which represented a direct challenge to the family-centric, suburban model favored by policymakers and elites.

The sinful side of the neighborhood flourished openly until it was forced into hiding by the U.S. military and the temperance movements that swept America before World War I. “The authorities discovered that 25 percent of all the men in the armed services were disabled by VD,” Field said. “So they passed a law banning brothels within five miles of a military base. The city had tolerated brothels, but the Red Light Abatement Act forced them to go underground. Then Prohibition in 1920 had the same effect on saloons and gambling. All the vice went into basements and speakeasies.”

Sin City prospered even in hiding, but a double whammy set it on the road to decline. “The big hotels in the southeast Tenderloin were banking on being part of a theater district, but after the quake the theaters moved north, to Geary and O’Farrell,” Field said as we walked along Powell towards Ellis. “The hotels had to readjust their sights to a lower class of tenants. Then the Depression hit and caused upkeep and maintenance on the buildings to go down.”

The neighborhood began to decline, but it was still clinging to respectability. By the 1930s, the typical Tenderloin resident in one of the SROs was a transient worker, a hobo or a step up from a hobo, someone who worked seasonally in the crops or in manufacturing. There were also a lot of merchant seamen. Bums had not yet appeared. (Groth cites a little mantra that concisely states the difference between bums, tramps and hobos: “A hobo works and wanders. A tramp dreams and wanders. A bum drinks and wanders.”) Some seasonal farm workers returned to the same rooming houses for 50 years.

“When World War II came the TL prospered again, with all the military around,” Field went on. “But after the war it slumped again. It briefly picked up again during the Korean War — in the 1940s and 1950s you have military shore patrols cruising through the area side by side with regular police.”

Horny GIs were keeping the Tenderloin on life support, but in the 1950s a number of things happened that sent it into a death spiral. Swing music played by big bands had drawn crowds into TL clubs; when the big band era ended, those clubs lost most of their audience. Bebop, the more harmonically advanced jazz that succeeded swing, was not nearly as popular. And the rise of folk music drew away still more paying customers. The last jazz club in the Tenderloin, the legendary Blackhawk at Turk and Hyde – where Miles Davis recorded two classic albums in April 1961 – went out of business in 1963. At the same time, the remaining theaters in the area, which had switched to showing movies instead of live shows, began to go downhill, becoming grindhouses.

Meanwhile, the neighborhood’s population was getting older and poorer. “The residents were aging and retired seniors living on limited means,” Field said. The big cafeterias where the people of the Tenderloin used to eat, Clinton’s and Compton’s – which in their heyday had table service — began their final descent. When the SROs were razed in other San Francisco neighborhoods in the early 1960s, their poor residents had nowhere to go except to the Tenderloin. “In the 1930s, the papers started calling this a ‘seedy neighborhood,’ Field said. “By the 1950s it was a ‘very seedy neighborhood.’ By the 1960s it was ‘a central city neighborhood.’”

Ironically, the arrival of the giant Hilton Hotel in 1963 accelerated the Tenderloin’s decline. “When it took over half the block on Ellis, a massage parlor opened on that block,” Field said. More followed.

From the 1950s, the TL had been the home of the city’s gay scene, with the action centered on the Kit-Kat Club (the Castro did not become gay until the 1970s). A 1966 mini-riot at Compton’s Cafeteria at 101 Taylor between drag queens and police is memorialized with a plaque in the sidewalk as an early battle in the gay liberation struggle, a precursor of Stonewall. (Since Compton’s, unlike the Stonewall, was not a gay bar, and what precipitated the brawl was a drag queen throwing a cup of coffee in a cop’s face, this claim seems dubious.)

The cultural upheavals of the 1960s sent runaways flooding into the Tenderloin. These boys and girls, the lost souls of the Flower Generation, hung out on street corners, doing drugs and prostituting themselves. The few working-class residents of the Tenderloin moved out as manufacturing jobs left the city. The housing stock deteriorated further. Then thousands of social outcasts flooded in during the 1960s and 1970s as prisoners were released from overcrowded jails and the mentally ill were de-institutionalized. “These people became a customer base for drug dealers, hustlers, and street criminals,” Field said. In the 1980s, the Tenderloin became increasingly black. The first homeless in the neighborhood were mentioned in the Tenderloin Times in 1984. “The 80s are when the Tenderloin actually becomes dangerous,” Field said. “When I started to work here.”

We turned down Taylor Street and approached the corner of Turk. A half-dozen men were milling around in front of a doorway. “This is the Tenderloin’s own private jail,” Field said. I looked more closely at the crowd. It was mostly young Latino men. One guy was wearing a Steeler’s jersey and gesticulating. They gave off a familiar sense of confused desperation mingled with bravado. “To get in there, you have to show i.d., have a reason to be there, and go through all kinds of security,” he said. “It’s run by a company that contracts with the state of California to house parolees, people on probation, awaiting trial. It’s cheaper for the state to keep them here.”

As we spoke, a young Latino guy a few feet away was talking on a cell phone. I paid no attention, but Field had street ears. “Did you hear what that guy just said? ‘Do you think he recognized me?’ That’s typical of the conversations you’ll hear on this corner.”

As we walked across Taylor, an ominous Indian-looking guy dressed all in black swaggered past, exuding a major don’t-fuck-with-me vibe. Field had street eyes too. “Did you see that?” Field said under his breath, pointing at the guy’s leg. A knife at least ten inches long was tightly strapped against his thigh. “Uh, I don’t think that’s legal,” I said. “Yeah. Well, maybe no one will notice,” Field said drily. “It kind of goes with his outfit.”

I asked Field what he thought was going to happen to the neighborhood. “The Tenderloin is the last battleground,” he said. “For non-profit housing outfits and social services, this is Fort Apache. It’s Custer’s Last Stand. Historically, poor people and improving neighborhoods don’t mix. Either the poor people move out or the neighborhood collapses. The Tenderloin is a case of the irresistible force meeting the immovable object. As a historian, I’m curious to see if the Tenderloin can resist the forces that always win out in cities.”

An example of the irresistible force was the impending gentrification, green-lighted by Mayor Ed Lee, of the blighted mid-Market Street area. Spearheading the assault on this legendarily bleak and intractable stretch was Twitter, which in June 2012 moved 800 employees into a building between 9th and 10th Streets. Though mid-Market is on the Tenderloin’s borders, the move was a portent. It struck me as ironic that a social media company, specializing in creating disembodied “communities,” might simultaneously destroy and revitalize the neighborhood that had once been a dense nexus of city life.

The immovable object, the thing keeping the Tenderloin from being gentrified, is a combination of city policy and non-profit housing entities, both dedicated to providing extremely low-cost housing in the heart of San Francisco. If it were not for these factors, the Tenderloin would look like any other revitalized downtown neighborhood, a high-priced 2012 version of Jane Jacob’s urbanist utopia.

The city made two crucial decisions, Field said. In 1981 it passed a law forbidding owners from demolishing SROs or converting them into tourist rentals unless they replaced the converted units or paid a fee into a fund for affordable housing. Then in 1985 it imposed height limits on new buildings in the Tenderloin, preventing Manhattanization. These decisions, combined with its active enforcement of rent laws — in particular, those preventing eviction of existing tenants — and its purchase of some SRO buildings, have helped keep market forces out of the Tenderloin.

Just as significant, non-profits like the Tenderloin Neighborhood Development Corporation and the Tenderloin Housing Clinic have purchased or leased many SRO hotels in the neighborhood, providing subsidized housing and social services for people who meet their criteria – those who are poor, disabled, have substance abuse problems, etc. Field said their rent is typically one-third of their monthly income, which means a lot of people living in the Tenderloin are paying less than $200 a month rent. (The median asking rent in San Francisco in December 2012 was $3100, making it the most expensive U.S. city in which to rent.)

As we stood on the corner, a young black guy stumbled up to us. “What are you doing?” he demanded, pointing to my notebook. “We’re just talking,” Field said. “No, no,” the black guy said. “You come down here to my neighborhood, you gotta…” “Look, my friend, it’s my neighborhood too,” Field said. “It belongs to all of us.” When he told the guy he had worked here for 12 years and had himself briefly slept on the streets, the guy’s jive bluster deflated like a pricked balloon. He seemed abashed and didn’t know what to say. We both shook his hand and he wandered off.

Field was deeply conflicted about what he wanted to see happen in the Tenderloin. “As a social worker, I want to do everything in my power to protect these people from the landlords who would throw them out. They’re evil motherfuckers. But as a San Franciscan, as a guy who likes to walk, I want all this stuff cleaned up.” He was sick of the crime, the prostitution (“as a social worker, I see absolutely no redeeming value in it”), the filth, the drugs.

“When I give my tours,” Field went on, “I ask how many people live in the Tenderloin. More and more people say they do. They’re in their 30s and 40s, they’ve been living here a few years. They’re invested in the neighborhood. OK, they go off to work and they relax. When they come home they get tense. How long will this go on? And then there are all the Southeast Asians with kids who have moved into the neighborhood. How long will they put up with this?”

In the end, Field came down on the side of letting it be. “I’ve got my dark glasses on so you can’t see me blushing,” he said. “But God help me, I do see it as romantic.”

The tour was over and I said goodbye to Field. I was happy that he had been my Virgil on this tour of San Francisco’s Purgatory. His ambivalence about the Tenderloin mirrored my own. Like him, I found it appalling and fascinating and consummately strange. And like him, I could not imagine San Francisco without it.

I went down Mason, turned on Turk and headed towards the setting sun. People were milling around in front of a defunct old porno arcade. It was still warm but a cool wind was kicking in from the west. I looked up at the rows of hotels and apartments, once-elegant buildings where countless ordinary working people had lived. All those vanished lives seemed to have sunk into their shabby lobbies and blank windows. In a city without memory, they were still here. There was a sadness about them as they stood there in the harsh slanting rays of the late-afternoon sun, but it was a sadness that was complete, like the peeled apple that falls from the father’s hand at the end of Ozu’s Late Spring. A sadness to keep.

Copyright © 2013 by Gary Kamiya Cool Gray City of Love: 49 Views of San Francisco Reprinted by permission of Bloomsbury

Illustration copyright © Jon Adams COOL GRAY CITY OF LOVE: 49 Views of San Francisco Reprinted by permission of Bloomsbury

Gary Kamiya is a Salon contributing writer.

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