Heading up Market Street the other day from City Hall to the Castro, we spotted her: a woman sitting on a concrete median in the middle of Duboce Avenue, her skinny, sore-covered legs and bright orange shoes hanging dangerously into traffic.

Supervisor Rafael Mandelman pulled over, and we tried to talk to her. But she just whispered incoherently. She’d strewn dirty clothes, chow mein noodles and plastic utensils around the median. The situation didn’t seem worthy of calling police, and she mumbled that she didn’t want an ambulance.

What to do?

That’s the question so many San Franciscans have as they pass people in obvious distress — high out of their minds or coping with mental illness — who desperately need help. But where does one get that help? Is there any real plan for them other than, possibly, a police order to move along, a quick stay in a jail cell or a brief visit to the overstuffed psychiatric emergency room at San Francisco General Hospital?

These questions prompted Mandelman and his staff in August to create an unusual list: the 17 most distressed and distressing people in his district, which includes the Castro. The iconic neighborhood — a birthplace of gay rights, the site of Harvey Milk’s camera shop, the place where the city’s giant rainbow flag still flies — has lost some of its luster as it’s become dotted with vacant storefronts, tent encampments, bicycle chop shops and scary street behavior.

Part of the problem is the city’s inability to deal in any meaningful way with those like the 17 people on Mandelman’s list. They’re the ones neighbors see all the time wandering into traffic, passed out on sidewalks, screaming into the air, flinging trash and harassing small business owners and their customers. One man on the list regularly digs his filthy hands into the pots of sweets at Giddy Candy and steals them. Another is often passed out drunk in front of the now-shuttered Cafe Flore.

Of the 17, three are women and 14 are men. They range in age from 28 to 73. They’re homeless or in and out of precarious living situations. They’re some combination of mentally ill, alcoholic or addicted to drugs.

The list is a mini-version of a longer one, totaling 237, that the city is using to bring intensive attention and services to those in the most dire need, to see whether their lives can improve along with the lives of everybody forced to deal with their behavior. Because of tight patient privacy laws, Mandelman doesn’t even know whether the 17 his office has identified are on the city’s longer list. So far, the effort to help the original 237 has been mixed — with 43 moving into permanent supportive housing, but scores still on the street and nine dead from overdoses and other chronic health conditions.

Mandelman meets monthly with representatives from the police, public health, homelessness and public works departments and representatives from neighborhood groups to check in on the progress, or lack thereof, of the 17. Can targeted, repeated outreach help them and the neighborhood at large?

More Information Inside the newsroom: Like the news articles The Chronicle publishes, our columns aim to be thoroughly reported, using interviews, research and data to back up the writer’s observations. But unlike regular articles, columns allow writers to offer their own perspective, and tell readers what they think about an issue. Heather Knight’s On San Francisco column is produced by talking to numerous sources, attending events across the city and interviewing a spectrum of people, including politicians, bureaucrats and regular residents. She writes from the press room at City Hall and gets her ideas from sources, reader tips and observations gleaned from her own life as a San Francisco resident.

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On paper, the answer should be yes. On a recent visit with him to the district, the answer was much more disheartening.

“We’re trying to coordinate a plan for each one,” Mandelman said. “But I’m not convinced we know how to do that.”

Mandelman said the reasons for the city’s lackluster results are many: the privacy laws that prevent even city supervisors from knowing any details about the health of their most disturbed homeless residents, the shortage of treatment beds and people to staff them, and the weak laws that prevent counties from compelling everyone who needs help into treatment. Mandelman and Mayor London Breed have pushed for stronger conservatorship laws, but other supervisors and homeless advocates have fought them over civil rights concerns.

These issues are personal to Mandelman. He grew up with a severely mentally ill mom, who’s since died, and essentially raised himself from age 11. He said he knows firsthand that inside many of these sad souls are lovely, coherent people struck down by bad brain chemistry.

“That’s not her best self,” Mandelman said of the woman with orange shoes. “There’s another person in there who — if she was getting the right care — might be able to emerge.”

The woman on the Duboce Avenue median wasn’t even on the supervisor’s list of 17, but she might as well have been. She was missing teeth, her face was smeared with dirt, and she whispered that she sleeps outside. It seemed wrong to just leave her there to perhaps get her legs crushed by a whizzing car.

“How in a civilized society do we have someone at this level of distress just being left here?” Mandelman said.

He called an aide in his office for advice, and she gave him the phone number for the city’s mobile crisis team, mental health experts who can respond to homeless people in crisis.

Or that’s the goal anyway. A woman who answered Mandelman’s call explained the team is based in the Bayview and wouldn’t be able to get there anytime soon. When she took his name and realized who he was, the attitude seemed to change. The team would get there as soon as possible, she said.

Social workers who interact with the same population, but not for the city, told me the team is great, but is very understaffed and sometimes takes up to seven hours to arrive. Jenna Lane, a spokeswoman for the Department of Public Health, said the team has 14 people who also respond to other crises, including homicide and suicide scenes, traffic collisions and police negotiations with people in crisis.

Clearly, San Francisco, with its $12.3 billion annual budget, needs to majorly beef up its crisis response and station the team more centrally because a rapid response is essential. It also needs to beef up its Homeless Outreach Team, which can also respond to women like the one on Duboce, but is similarly stretched thin and often slow to respond.

Mental Health SF, a new City Hall plan to overhaul the broken mental health care system, would create a new Crisis Response Street Team to help people in crisis on our streets, but funding hasn’t been secured and the changes are a long way off.

We stayed with the woman with orange shoes for a while. She eventually left the median for a safer sidewalk. She talked about being from North Korea and about being dead. Eventually she walked away, headed east down Market Street.

Mandelman kept in contact with the mobile crisis team via text, and the van finally found us about 45 minutes after he first called. He told the team where we’d last seen the woman with the orange shoes, and they said they’d drive around to try to find her.

We headed to talk to Mat Schuster, owner of Canela Bistro on Market Street, who’d texted Mandelman’s staff that day in frustration. The night before, a panhandler outside the restaurant had gotten angry that nobody was giving him money and threw a patio chair at the restaurant’s front window — as diners sat in the window inside. The glass shattered, but fortunately nobody was hurt.

“The customer chatter was, ‘This is San Francisco now,’” Schuster said.

Which is the saddest thing I’ve heard in a while.

Across the street, Mandelman and his staff spotted Individual B on their list of 17. He’s a tall, big man who’s often happy and smiling, but can turn violent and aggressive. He’s known for being a hoarder, and he’d spread a cushion, clothing, a bucket and trash around Jane Warner Plaza.

Individual B told us he’d been offered a bed at the Navigation Center on the Embarcadero, but it wasn’t clear whether he was going to take it. He was hard to talk to because he was almost entirely focused on staring at himself preen and dance in the reflection of the window of Twin Peaks Tavern.

“I’m an American,” the man told me. “Aren’t you American? You’re my cousin, aren’t you?”

Mandelman sighed.

“It’s been six to eight months, and whatever we’re trying ain’t working,” he said, referring to the fact Individual B has been on the list since its creation last summer. He shook his head as one neighbor after another approached him to complain about needles or trash or whatever.

Mandelman said he understood the frustration.

“I’m the supervisor,” he said. “I’m the face of a city that’s failing.”

Mere feet away was Individual M on the list. She’s known for wandering into traffic, and that’s what she was doing when we spotted her. She’d stand in the street in front of cars trying to turn right and came within inches of being whacked by a Muni bus. She’s known as “Princess Leia” in the neighborhood for sometimes wearing her hair in two buns on the side of her head — held in place at times with syringes.

She darted her eyes nervously and kept muttering to herself.

“I don’t want to talk right now,” she told me. “I’m really scared.”

People call 311 and 911 about her all the time, and yet she’s always back there, darting into traffic.

Mandelman is tired of the city’s approach, which focuses mostly on outreach workers trying to build a relationship with people over time in the hopes they’ll eventually accept help. He wants the city to take stronger action — and he wants the state to adopt more expansive conservatorship laws to compel people into care. The state’s law was strengthened a little recently, but it’s still a very high bar to force people into treatment if they say they don’t want it.

The loud whir of Castro and Market streets — the clearly deranged people and the incredibly frustrated neighbors who kept stopping to complain — became too much for Mandelman. He held a finger up, as if asking for a pause in our conversation, and his eyes filled with tears. He walked away for a while.

“It’s upsetting. There’s so much misery,” he said when he returned, his voice rising in anger. “It’s insane that we cannot solve this. This is solvable. The solutions are obvious to all of us.”

Obvious, maybe, but not easy. He wants stronger conservatorship laws and more of the city’s money directed to treatment beds so there’s somewhere to put those who are picked off the streets and mandated to accept care.

“She’s terrified,” he said, nodding to Individual M, still walking in traffic.

“He’s off his rocker,” he said, motioning to Individual B, still preening in the window.

“This is just wrong,” he continued. “This neighborhood is so important. It’s where queer politics started. It’s an internationally known, iconic neighborhood, and it’s suffering under civic failure.”

Mandelman was done. We walked back to his car. He checked with the mobile crisis team. They had not found the woman with the orange shoes.

San Francisco Chronicle columnist Heather Knight appears Sundays and Tuesdays. Email: hknight@sfchronicle.com Twitter: @hknightsf Instagram: @heatherknightsf