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I Went On a Police Ride-Along in San Francisco's Worst Neighborhood

The Tenderloin is San Francisco's most notorious neighborhood. It's as close as you can get to an open-air drug market in one of America's wealthiest cities. The police there have a friendly, yet parental relationship with the residents.

A woman in jeans was cuffed to a metal railing inside San Francisco's Tenderloin police station when I walked in late Friday afternoon—prepared for just about anything during my ride-along through one of the most notorious open-air drug markets on the West Coast.

The woman in cuffs had been arrested on suspicion of selling drugs, and was about to be strip-searched. A few feet away from her, in the cramped station interior lit with fluorescents, a plainclothes cop counted bills and crack that he'd seized. Strip-searches are standard procedure for drug arrests.


Men and women (most of the dealers in the Tenderloin are women) hide drugs in every orifice in the human body, including lady-parts; a tactic that the Tenderloin cops nicknamed "the Vault." It's also why most dealers in the neighborhood are women. And often dealers will sell directly from the Vault, insisting their buyers put the secreted drugs into their mouth. "Chipmunks," they're then called.

"Welcome to the Tenderloin," said Sgt. Shaughn Ryan, the cop I'd be paired with for the night.

If you aren't familiar with the Tenderloin, it's a tiny triangular neighborhood located downtown, just a few blocks from San Francisco's City Hall and about a five-minute walk from Twitter's HQ on Market St. It's famous for the drug trade; a trade that's not controlled by gangs. Dealers operating within its boundaries are relatively free to offer drugs without paying tax to gangs.

The Tenderloin is unofficially organized kind of like a department store for drugs. Each corner has a different specialty drug, which is constantly rotating. For example, at the time of going to press, Turk and Taylor Street is where you'd go to buy crack. Turk and Leavenworth Street is a good place for prescription drugs. Along other streets it's possible to score meth, coke, weed, heroin, anything else you can think of. And, like a department store, regulars commute from other parts of the Bay Area to score or sell.


It's worth noting that along with the drug trade and the oft-decrepit, vermin-infested residential hotels, about 4,000 children go to school in the area, several hundred of whom walk home alone. The neighborhood houses families, often immigrants, who are struggling to make their way in the city.

Sgt. Ryan is an interesting cop. Originally from the Northeast, he's been at the Tenderloin station for three years, and in the SFPD for 17, about 12 of which were spent working as an undercover cop on the narcotics beat in some of the most dangerous neighborhoods in San Francisco.

He looked like what I would have expected: clean-shaven, bulky with the body armor on. He spoke, and told stories with the cadences and patterns of a career officer, used to dealing with crooks, liars, and dealers for nearly a quarter-century. When I asked what makes him serve, he told me, "I don't like bad guys, and I don't like bullies."

"Nowadays, you can't just be tough either, you gotta be smart," Ryan said, adding that he's got to be part medic, psychologist, lawyer, drug counselor, and cop to deal with the range of cases he encounters. "San Francisco doesn't tolerate ignorance from its civil servants." From what I saw, it was all true.

Sgt. Ryan kicked off the evening with a tour of the neighborhood, angling his big SUV in a tight, circling patrol along the neighborhood streets. With no traffic, it takes less than five minutes to drive from one end of the Tenderloin to the other.


A couple of right turns from the station later, we rolled through the intersection at Turk and Taylor Streets; the place to buy crack in San Francisco.

It was straight out of the The Wire. It looked and felt like Hamsterdam would if it were real. There were dozens of people—some dealers, some addicts, some just hanging out on the street. It's hard to tell who's doing what; buying drugs, selling drugs, drinking and smoking, or just shooting the shit. Ryan said nice shoes usually indicated a dealer. It smelled like cigarette smoke and cheap booze, with a bit of moisture from San Francisco's famous fog.

I found out later from another cop that there's a well-understood system of social behavior, and that if you observe from a building above for an hour or so, it gets a lot easier to figure out what's going on.

When on patrol, cops in San Francisco drive with their windows down, so they can hear everything going on outside. Ryan, to waved and called out to people from the driver's seat. The cops have an odd, friendly relationship with the crooks.

Out of the throng, a black woman with wild, frizzy hair, short-shorts, and a bit of a potbelly started screaming in our direction. "Fuck you, I'll fucking kill you," she shouted into the open window on the passenger side, a foot or so from my face. I flinched.

"Yeah, yeah Janet," Ryan said totally taking it in stride. He just kept right on driving slow. He must have seen shock on my face because Ryan immediately said, "Don't worry, I won't put you in harm's way." I believed him.


The cop had nicknamed the screaming woman "Janet Jackson." She was a well-known Tenderloin resident, and harmless according to Sgt. Ryan. "She was just putting on a show for you," he said. The next time we pulled around—and we did so more times than I could count during the evening—she didn't scream at us. As much.

The first call we responded to was a suicide threat. I didn't really hear the call come in over the radio, but mid-sentence Ryan gunned the engine, and sped through Friday rush hour traffic.

The call came from a halfway house for the chronically homeless on Mason Street, just a couple blocks outside a deeply entrenched part of the drug market. Ryan figured out who the suicide threat came from in about half a second. The guy wasn't in good shape: White, in his twenties, with a scruffy beard a ratty clothes. He looked at me uneasily.

"How did you plan to kill yourself?" Ryan asked.

"Hanging," the guy said.

"Are you in any treatment programs? Or on drugs?"

He mumbled something about being in a treatment program.

A couple other officers arrived on the scene, one of whom was a negotiator. One of the cops asked again, "Are you planning to kill yourself?" After a second "yes," the officer unhooked cuffs from his belt and, without asking, the victim turned around as if it wasn't his first time.

As it turns out, he probably knew the routine. Once we got back into the SUV, the sergeant explained that people in need of drug or other kinds of medical treatment know they can get a ride from the SFPD if they act as though they are a danger to themselves.


That fact didn't bother Ryan. The guy had a legitimate problem. What annoyed him was the fact that trips to San Francisco General Hospital tied up two of his officers for several hours; transportation through rush hour traffic, paperwork, waiting times at the hospital. The frustration was that there was no other government mechanism to deal with these problems. That night there were a total of three cars in the neighborhood. Now only one of them was free.

"If I have only two cops responding to a multi-subject incident such as a shooting or a domestic violence call, those officers might be outnumbered and in danger," Sgt. Ryan said.

A second dispatch came in, interrupting our conversation. We received a report of a man lying unconscious outside the New Century Theater, a strip club on the Tenderloin's outskirts.

It was growing dark when we arrived, the sky pink as the sun dropped over the horizon. The unconscious man was a white guy, with short black hair, wearing a gray hoodie. When we found him, he was unconscious on the street; his head partly propped against the side of the club's outside wall. Blood was oozing from a wound in the back of his head. Sgt. Ryan checked him out, but waited for the paramedics from the San Francisco Fire Department to show up and handle his medical concerns.

Dispatch had reported the guy got shoved into the wall, but according to surveillance footage quickly retrieved by other officers who arrived moments after we did, the guy was drunk—maybe high—and had been stumbling down the street, until he ran into the wall, and collapsed.


I watched them load the guy onto a stretcher and into the ambulance. The club owner had gotten chatty with Ryan, and they exchanged business cards as this was all going down.

It was eerie how routine it all felt. Sgt. Ryan said that the paramedics were worried about the guy—it showed—and were rushing to get him to the hospital. That was going to be one hell of a hangover, if he ever woke up.

Sometime after dark, shit got heavy. "At night all the real scary bad guys come out," he said, adding a quip about how when the big predators come out to hunt, the little guys crawl under rocks.

As if to illustrate the point, when Sgt. Ryan pulled our SUV around the corner of Golden Gate Avenue and Taylor Street, he spotted another truck, parked, tinted windows mostly down, beats thumping.

He crept our SUV up along the passenger side slowly. At the same time, he brought his right hand to the pistol on his hip, ready to draw and shoot. At that moment I realized how volatile the Tenderloin really was.

It turned out to be nothing. Whoever was in the SUV rolled the windows up and turned the music down. Satisfied, we drove off.

Cops in the Tenderloin have an interesting relationship with people they know are criminals. First, cops know a lot of names and the dealers (or at least the smart ones) know the cops. Many of them are informants, too. Dealers don't like violence, it's bad for business, so most of them don't mind telling the cops when people start shooting each other.


Later on, we pulled up to a corner where three guys who he said were probably slinging pills or crack. He stopped the truck. The sergeant just sat there in the SUV and waited, window down. "How you guys doing tonight," he called. No response. Two of the guys lit smokes, one guy took off right away. After thirty seconds or so Ryan commented that he was impressed the dealers played it so cool. Usually, guys split right away. After another minute, the corner was empty.

One of the last calls we responded to was a taxi fare dispute with a particularly uncooperative, and potentially dangerous, passenger. Ryan really hauled ass to get there—driving the wrong way down one ways, hitting bursts of the sirens while we crossed an intersection—it was some real COPS shit, except all very, very real, and I was in the front seat.

By the time we arrived, a half dozen squad cars and a whole bunch of cops were trying to cuff the suspect. The entire block was shut down. The guy was wearing a dress shirt and suit pants, and he was screaming. He was yelling about the cops, that he had a broken arm, then started saying that he wanted his lawyer there. Ryan didn't jump into it. Too many cooks in the kitchen, I guess.

The reason for the seemingly overwhelming response is that the block was a dangerous one for police, Sgt. Ryan said. It's because 111 Taylor Street is a halfway house for federal and state parolees; guys who don't like cops much. "It's like having several hundred people in a prison without bars." It was "not uncommon" to have an anti-police mob form, or have a toaster oven drop from several floors above.


Just as the cops were cramming the suspect into the car, Janet Jackson showed up, checking out the commotion. Still wearing her short-shorts and t-shirt, she started to loudly admonish the cops. The dozen cops half-listened for a moment, and then, at the same time it seemed, turned back to their business, waving her off, or telling her, "get outta here Janet."

The rest of the night was quiet—at least for the Tenderloin. But, as Sgt. Ryan and I were parting ways, a confessed meth addict, "new in town," approached us about helping the SFPD with a buy bust; something he was hoping to get paid to do. Sgt. Ryan told him to come back tomorrow.

The neighborhood has unmistakably changed in the last several years. Its borders are slowly shrinking as the surrounding gentrification slowly creeps deeper and deeper into the neighborhood. There are tech companies such as Twitter and Square that have set up offices on nearby Market Street. Also, Wework, a New York based co-working company just bought a building at Turk and Taylor Streets—the crack corner—and is converting some of the upper levels of a theater into office space for startups. And there's a two story brewery and restaurant opening on that corner in the future too.

The feds have apparently gotten serious about "doing their part" and have begun to crack down on the drug trade. A few weeks ago, the US Attorney for Northern California announced 11 grand jury indictments of alleged dealers. The indictments are serious, and because most of the Tenderloin is within 1,000 feet of a school, the penalties are severe: a mandatory minimum of a year, with a maximum sentence of 40 years, and up to a $2 million fine. It's clear, Uncle Sam has put the dealers on notice.

It's hard to know how much of an effect crackdowns and enforcement have on the neighborhood. According to Sgt. Ryan what will change the Tenderloin isn't more cops, or stricter enforcement, or even federal drug raids, it's gentrification. He thinks that rising tide of new money has had, and will have, a far more profound effect on the neighborhood's character. That's debatable, considering the proliferation of drug treatment centers and harm reduction techniques.

Regardless, don't hold your breath. The small section of the city patrolled by the Tenderloin police continues to be a neighborhood wracked by violence and drugs, with a transient population made up of some of San Francisco's very poorest residents.

On my way out of the station for the last time I heard one of the officers quip, "It's a dump, but it's our dump."

"Good cops need to have pride," Ryan said, by way of explanation. "Tenderloin officers know that this is a hard and unforgiving place. But there are a lot of good people here, even if we, the police, don't interact with them much."