Skip to main content

Is San Francisco’s best strategy in homelessness lawsuit to lose?

tents are seen along a sidewalk
A Department of Public Works cleaning truck waits near a homeless encampment on Larch Street in San Francisco on Feb. 28, 2023. | Joe Dworetzky/Bay City News Foundation | Source: Joe Dworetzky/Bay City News Foundation

On Dec. 23, 2022, San Francisco’s unsheltered population got a Christmas present of sorts: They were allowed to continue to sleep on the city’s sidewalks.

U.S. Magistrate Judge Donna Ryu forbade the city from enforcing, or threatening to enforce, a variety of laws and ordinances that would otherwise “prohibit involuntarily homeless individuals from sitting, lying, or sleeping on public property.”

The order came in the form of a preliminary injunction in a federal lawsuit brought against the city by the Coalition on Homelessness, an advocacy organization, and a number of individuals, some formerly homeless.

The injunction was preliminary in that there had not yet been a full trial on the merits—that was at least a year away—but Ryu found the conditions were so bad and plaintiffs so likely to ultimately win, that it was in the public interest to enter temporary relief until the full trial could be held. 

The judge based her ruling on the fact that the city did not have sufficient beds to provide shelter for the city’s unsheltered population and therefore enforcing the sit/lie/sleep laws against the plaintiffs was punishing them for the status of being homeless. In her opinion, that violated the Eighth Amendment’s prohibition on cruel and unusual punishment.

READ MORE: Here’s What Unfolds When San Francisco Homeless Encampments Get Cleaned

The city’s reaction was swift. San Francisco Mayor London Breed said flatly, “Mayors cannot run cities this way.”

San Francisco’s City Attorney David Chiu took the relatively unusual step of issuing his own press release.

Chiu said that the judge’s order put the city in an “impossible situation” and announced he was immediately filing a motion to get relief from an expansive reading of her order.

Five months have now passed since the press release, and Chiu has had little luck getting any relief from the court’s ruling. Some of the difficulty is because he is stuck with “bad facts,” as lawyers like to say, and some of it is because a few strategic decisions have backfired.

But there is a much larger question to ask about the city attorney’s strategy: does it actually make sense to try to win this case?  

Thus far, it looks like this may be one of those cases where the best way to win is by not winning.

San Francisco City Attorney David Chiu speaks at a press conference in August 2022. | Benjamin Fanjoy for The Standard

Public Litigation 

High-stakes, high-visibility lawsuits involving governmental bodies, elected officials, large amounts of money and potential structural changes in the way government works—cases referred to as “public cases” or “public litigation”—are like mountains so tall that they make their own weather.   

Coalition of Homelessness, et al. v. City of San Francisco, et al. was one of those cases. It cut to the core of one of the most intractable, expensive, frustrating, painful, depressing, divisive, and monumental problems that the city had ever faced.  

You could go back to Mayor Dianne Feinstein’s efforts in 1982 to launch faith-based emergency shelters and soup kitchens and roll it forward, mayor by mayor— Agnos, Jordan, Brown, Newsom, Lee, Breed—one after another, each putting out a new program and spending millions and millions to address the problem of citizens sleeping on the street. But for all the effort and spending the problem would not go away.

It was profoundly embarrassing to the self-esteem of the city—this was, after all, the place of big ideas, of innovation, the place that changes the world—but all of those things had not been enough to turn the tide. 

And now in a sign of how thoroughly the city’s leaders—one by one—had failed, this problem had bounced from City Hall to the federal courthouse where the city’s political leadership would not be leading; they’d be reacting to what some unelected judge said.

A Department of Public Works employee speaks with a man before clearing an encampment clearing on April 25, 2023, in the Mission District in San Francisco. City workers bulldozed a line of tents in a SoMa alleyway, enraging activists. | David Sjostedt/The Standard


From the very start, it was clear that the city attorney’s office was in for a dogfight.

The plaintiffs were no ragtag bunch of hippies and do-gooders stumbling into federal court. The Coalition on Homelessness had been around for 35 years and was led by Jennifer Friedenbach, a smart, capable and tough woman with a 25-year history of community organizing around housing, welfare rights, disability, and homelessness issues.

They’d enlisted accomplished lawyers, including Zal Shroff, a former clinical lecturer at Yale Law School who worked at the Lawyers’ Committee for Civil Rights of the San Francisco Bay Area, and John Do, a senior staff attorney at the ACLU of Northern California. They also had a pro bono lawyer named Alfred C. Pfeiffer Jr. from Latham & Watkins LLP.

Latham was ranked No. 5 on Vault’s 2023 list of the top 100 American law firms, a 3,000-lawyer behemoth filled with lawyers who knew what they were doing in federal court.

Lawyers from Latham had argued the seminal case of Martin v. Boise in the U.S. Court of Appeals for the 9th Circuit, the case that said that a city cannot make criminal the practice of sleeping on city streets when there is no other practical place to go.

When plaintiffs filed their lawsuit on Sept. 27, 2022, they had been gathering evidence for more than two years. Their complaint was 101 pages. On the same day as the lawsuit, they filed their motion for a preliminary injunction. That filing was only 36 pages, but it had 970 pages of exhibits attached.

The plaintiffs alleged that despite city law and policy that forbid the city from clearing encampments without first giving notice and offering the displaced residents shelter, the city routinely conducted “sweeps” that closed encampments without providing either.

The plaintiffs submitted affidavits from people who had seen sweeps and been swept. Perhaps even more powerfully, they had affidavits from former city employees who observed the city’s sweeping practices and found them so inhumane that they were now offering testimony on behalf of the coalition.

Among the exhibits to the motion was a 53-page declaration of Christopher John Herring, an assistant professor of sociology at the University of California Los Angeles who focused his academic work on “homelessness, housing, poverty, criminal justice, and welfare.”

In an affidavit, he summarized some of the qualifications he brought to the assignment: “Between 2014 and 2015, I conducted an ethnographic study of San Francisco’s unhoused population. During the course of the study, I spent 57 nights sleeping out on sidewalks, parks, and beneath underpasses in San Francisco; 96 nights living among hundreds of other men in shelters; and 76 nights staying in daily or weekly hotels with people who were marginally housed.”

He issued five expert opinions that may be distilled this way: 1) voluntary shelter in San Francisco has been systemically unavailable since COVID; 2) the city through the “Healthy Streets Operating Center,” or HSOC, clears encampments despite the lack of shelter; 3) HSOC uses police enforcement against those in encampments; 4) HSOC destroys the property of the unsheltered on a wide-spread basis; and 5) the above practices cause serious and irreparable harm. 

Judge Donna M. Ryu | U.S. District Court

Judge Ryu held a hearing on Dec. 22, and the next day she ordered the preliminary injunction.

Against the mountain of evidence submitted by the plaintiffs, the city’s evidence was, in Ryu’s opinion, “thin” and mostly a recitation of its written policies while avoiding the plaintiff’s core argument that the city’s policies were fine—it was, she said, the city’s lack of fidelity to its policies that was the problem.

Ryu found that “It is beyond dispute that homeless San Franciscans have no voluntary “option of sleeping indoors,” and as a practical matter “cannot obtain shelter.” From there she followed the existing law announced in Martin v. Boise that said the city cannot make criminal the practice of sleeping on city streets when there is no other feasible option.

The Meaning of the Injunction 

The ink on Ryu’s order wasn’t dry before a fundamental question arose.

Ryu said that the sit/lie/sleep ordinances could not be enforced while there was a shortage of shelter beds. But what did that mean? If the city was clearing an encampment of 20 people and the city had 20 beds available and offered one to each of the people who were being dispossessed, was that good?

That seemed like a reasonable reading and if it was correct the city could keep clearing encampments despite the injunction, though it would have to be scrupulous to make sure that it didn’t get ahead of the beds that were actually available at that time.  

But there was another possible reading of her order, and that one had profoundly different consequences.

What if Ryu meant that the ordinances couldn’t be enforced unless and until there were enough beds for everyone who was unsheltered? There was no disputing that the city had a severe shortage of shelter beds. The shortage was so desperate that the city had essentially closed the shelter system to homeless individuals signing up on their own accord.

The only beds available were those that freed up on a day-by-day basis from the churn as people in shelter left for housing or to return to the streets. Those beds— never a lot—were under the control of city officials and could be doled out at an encampment resolution, but they were far short of what was needed for all the city’s unsheltered.

The numbers made this painfully clear. As of February 2022, the time of the last official homeless count, there were 7,754 unhoused individuals in the city of San Francisco, roughly one percent of the population. Of that number, 4,397 were “identified as sleeping in unsheltered locations.”

If Judge Ryu’s order meant that all the city’s unsheltered individuals had to be sheltered before an encampment could be cleared, the city would need 4,397 more places of shelter, or at least enough to cover all those who did not reject their offer of shelter.

How much that would cost was far from clear, but the city’s Department of Homelessness and Supportive Housing (HSH) recently reported that it would cost between $60,200 to $73,000 per year just to keep a person in a shelter bed, and that didn’t take account of the upfront capital costs of getting the bed in the first place.

Whatever it added up to, it was a massive amount of money and if even it was theoretically doable because of the monumental tax base of San Francisco, the lived experience of city officials was that it was painful and difficult to find an appropriate site that could accommodate even 100 or 200 people, much less get a homeless facility approved over community objections. There was no way that 4,000 shelter beds were going to somehow magically appear.

Mayor London Breed tours a bedroom at the 711 Post St. shelter in San Francisco on July 19, 2022. | Benjamin Fanjoy for The Standard

Two Narratives of Homelessness 

There was a long and fraught history to the city’s response to homelessness. Over four decades, public discussion had been dominated by two narratives.  

One narrative was that tent encampments and the filth generated by unsheltered people congregating in small villages without sanitary services on the streets were destroying the things that made the city great. Unwashed encampment dwellers have made and would continue to make the bad personal choice to sponge off the taxpayers—who, by the way, were working hard just to feed their kids—and the only way to discourage that sponging was, well, to actually discourage it.

The other narrative was that in a place with the wealth and talent of San Francisco there must be a way to compassionately engage the homeless and get them into shelter and housing so that they can access the mental health and/or addiction services so many of them need. Anything less would be an abdication of the generosity and greatness that made this city the best big city in the country. Big Ideas. Innovation. We can change the world.

Those two narrative threads—positions of equal dignity in the abstract—appealed to different segments of the population and like all political narratives, ebbed and surged with the passage of time and the occurrence of new events.

And while of course it was far more complex and nuanced than labels can convey, it is nevertheless helpful to see the two narratives as a clash between the policy of enforcement—homelessness is best addressed by enacting and enforcing laws against camping on city streets—and the policy of public health that says the answer is to provide housing and social services to help those living on the streets get to a better place.

People like on a San Francisco street
People lie on the ground of a sidewalk in the Tenderloin District in San Francisco on July 4, 2022. Homelessness and public drug use continue to be major public health issues in the neighborhood. | Benjamin Fanjoy for The Standard | Source: Benjamin Fanjoy for The Standard

Chiu was appointed by Breed on Nov. 1, 2021, to fill the remaining term of the highly regarded Dennis Herrera. Chiu brought an extraordinary background to the job. He had serious credentials: triple Harvard, law clerk for a judge on the U.S. Court of Appeals for the 9th Circuit, elected member of the city Board of Supervisors with three consecutive terms as years as board president and had served four terms in the state Assembly representing east San Francisco.

There was also a nice irony in the fact that early in his legal career he worked as a civil rights attorney with the Lawyers’ Committee for Civil Rights, the same organization representing the coalition in this case.

He clearly had superlative political skills. And while that might not matter much in the ordinary hurly-burly of city litigation, in the trenches of a high-stakes public case, they could be invaluable.

That said, the case got off to a rocky start.

After saying Ryu’s order put the city in an impossible situation, Chiu’s press release of Jan. 3 said he’d be filing a motion to “clarify” the order.

The primary reason to issue such a statement is the hope that it will sway public sentiment and that will nudge the judge to do the right thing.  But judges, particularly federal judges, can be prickly about being nudged that way.

Moreover, a lawyer has to be careful when he or she asks a judge to “clarify” an order, particularly when the clarification is a matter of such importance as it was here. Seeking “clarification” on a weighty issue could seem disingenuous.

On Jan. 3, Chiu’s lawyers filed an “administrative motion,” one of those housekeeping filings that lawyers use to get permission to file a brief that exceeds the allowed page count. They got smacked down.

The judge told them that wasn’t the way to proceed. “You know better,” she said.

City Attorney David Chiu speaks at a press conference at San Francisco City Hall on Aug. 4, 2022. | Camille Cohen/The Standard | Source: Camille Cohen/The Standard

She denied the motion and told the city lawyers that if they wanted her to consider their argument they should come back in the proper fashion. (The city wasn’t alone on this; the Coalition tried the same approach on one of its issues and got the same response.)

Meanwhile, the injunction stayed in place.

But a funny thing had happened. Now it was as if the interpretation that Chiu worried about—the one that put the city in the impossible situation—was what the order actually said. Ryu didn’t say that—and it might even have been the less likely of the interpretations a fair reader would have given the words she wrote—but by asking for the clarification and not getting it, Chiu—or at least his office—had given dignity to that interpretation.

Despite her invitation, the city did not go back to Judge Ryu with a motion to determine or limit the scope of her injunction. Instead, city lawyers filed an appeal to the 9th Circuit.

There was nothing wrong with appealing, that was expected. But now armed with a pending appeal, Chiu’s team returned to Judge Ryu and asked her to suspend her injunction while the appeal was pending. To support that request, they repeated the argument about the impossible position the city was in and how it was not feasible to leave all encampments in place until the city somehow produced 4,000 shelter beds.

Ryu denied the request. The city might well have lost anyway, but the city lawyers’ approach clearly bothered Ryu.

She emphasized that even though she had invited the city to raise the issue properly, it had declined to do so. In her view, the city’s legal gambit deprived her of an opportunity to consider the city’s argument in the context of a proper factual record—witnesses, testimony, evidence—the way important issues should be decided in a court of law.

So, the injunction remained in place.

In an interview, Chiu acknowledged that the beginning of the case was challenging.

He said the plaintiffs have a large legal team, and “we have had to staff up overnight.”

However, he emphasized that the office has committed eight attorneys to the case, in addition to himself. “That number of attorneys is equivalent to the size of any of our teams that are advising major departments in the city,” he said.

Chiu said the city team “has been working around the clock to address the issues that have been raised.”

The resources he has devoted to the case are “a function of how important it is for us that this case is decided correctly and what the significance could be if it’s not.”

And that is not just true in San Francisco. Chiu noted that other government organizations have filed amicus or “friend of the court” briefs in the 9th Circuit supporting the city’s position, including the National League of Cities.

“This case,” Chiu said, “is being watched by cities and states, not just in California, but within the 9th Circuit and beyond.”

Painted squares mark socially distanced camping spots for a temporary sanctioned homeless tent encampment across from the San Francisco City Hall amid the coronavirus epidemic on May 28, 2020. | Liu Guanguan/China News Service via Getty Images

Resolutions vs. Sweeps

At the root of the lawsuit are what the city called “resolutions” and the advocates called “sweeps.”  

Proposition Q, the local ballot measure passed in 2016, provided a strong Enforcement message: encampments on city streets were illegal and the city was authorized to clear them.  

But Prop. Q also sent a strong Public Health message: The city could only clear encampments if certain conditions (incorporated into local law by Section 169 of the Police Code) were first fulfilled. Key among them, there had to be advance notice and there had to be an offer of shelter or housing.

But while it was easy to braid the Enforcement and Public Health policy strands together in the dainty language of an ordinance, the different aspects of the effort were committed to different city agencies who didn’t always play well together.

Enforcement was primarily the Police Department along with the departments of Public Works, and Emergency Management.

Public Health was the focus of HSH and the Department of Public Health.

In an attempt to eliminate inter-departmental friction and coordinate the response, in 2018, the city created HSOC, pronounced “aitch-sock.”

HSOC was not an agency, and had no independent budget, but was styled as a “command center,” originally within the police department and later emergency management.

The advocates say HSOC ran a complaint-driven system. Neighbors, business representatives, and public officials would report illegal encampments. HSOC’s mission was to get rid of them.

In the city’s terminology, a visit by city workers to a tent encampment was an “engagement” and should that engagement result in the encampment being cleared from the park or sidewalk, the city would record it as a “resolution.” In other words, the way the city saw it, an encampment was a problem that needed to be “resolved.” In the opinion of the advocates, bringing the residents into shelter was a secondary consideration for HSOC.

The advocates called the city’s visits “sweeps,” and not because the city brought in trucks full of cleaning personnel—though they definitely did. The advocates saw the purpose of the operation as harassing the homeless and sweeping away the problem they presented.

Shroff, one of the coalition’s lawyers, says that one of the main purposes of the coalition’s lawsuit is “truth-telling” about what he says is “the disparity between the image of what the city says its response to homelessness is and the actual practice on the ground.”

He said the public is being told by the city that it has a plan that is “a proactive, humane solution to homelessness that is being carried out, that is costing millions of dollars. And then when the taxpayers don’t see that plan working, they’re understandably frustrated. And so, what they call for then is criminalization of homelessness.”

A person with a clipboard conducting the homeless point-in-time count.
Gigi Whitley, a Department of Homelessness and Supportive Housing deputy director of administration and finance, marks a tally sheet during the 2017 Homeless Point-in-Time Count as Gregory Clark sits in a wheelchair on the street in San Francisco. | Lea Suzuki/The San Francisco Chronicle via Getty Images | Source: Lea Suzuki/The San Francisco Chronicle via Getty Images

Limited Engagements 

The city continued its practice of engaging with encampments despite the injunction.

That was fine in and of itself; Ryu’s order did not prevent the city from engagements.

The judge had no problem with the city keeping the streets clean. The city could require tents to be moved for a few hours, so the city could hose down the pavement and cart away refuse and trash.

There was also no problem with the city visiting encampments to offer shelter or services to the residents. That was in everyone’s interest.

And the injunction did not limit the city in enforcing the laws about drugs or violence or anything other than the sit/lie/sleep ordinances.

However, the coalition did not trust that the city would work within those limitations and sent volunteer observers to document what was happening with the post-injunction engagements.

They concluded that the city was not complying with the injunction. They said that the city workers were using the engagements to harass the homeless and pressure them to break up their encampments.

As early as January the coalition telegraphed that it was going to ask the court to appoint a “special master” to oversee the enforcement of the injunction. They filed a formal motion to that effect on May 25, and a hearing on that issue is scheduled for Aug. 10.

While the coalition has not asked for the city to be held in contempt of court, a special master could be a foot in that door.

A homeless person sits outside of Westfield San Francisco Centre on Market Street in Downtown San Francisco on May 4, 2023. | RJ Mickelson/The Standard

A Safe Place To sleep, a Safe City To Visit

 Even before the coalition filed suit, some members of the city’s Board of Supervisors were asking what it would take to actually provide shelter for everyone that needed it.

Supervisor Rafael Mandelman was getting an earful from employers in his district who made it through the pandemic by the skin of their teeth and were trying to hang on in the new reality of diminished tourist dollars and tech companies who had let their personnel go fully remote.

Barbara Perzigian, general manager of Hotel VIA located near Oracle Park, speaking ahead of a hearing at City Hall, said, “I just want to start out by saying that anybody that is in a leadership position in this city … needs to hear it very clearly. No one wants to come to San Francisco.”

She continued: “Everybody knows San Francisco and Paris used to trade places as the two top cities in the world where everybody wanted to go. Well, now San Francisco is on the bottom, and it’s become the city where no one wants to go.”

“We don’t have three years to wait because we’re all going to be out of business. We need to clean up the streets,” she said.

Mandelman led a charge to get his colleagues to take a new approach to the homeless situation. He began to say that the city’s de facto policy was to use the city streets as the waiting room—a multi-year waiting room—for housing.

Mandelman wasn’t against providing housing for people experiencing homelessness, but he was very conscious that the city had a profound housing shortage, was one of the most expensive places in the country to build housing, and the types of housing that were appropriate for some of the unhoused required significant “supportive” services for the housing adventure to work.

Supervisor Rafael Mandelman speaks during a press conference.
Supervisor Rafael Mandelman speaks at a press conference in San Francisco on Sept. 6, 2022. | Paul Kuroda for The Standard | Source: Paul Kuroda for The Standard

Put it all together and housing for all was a massive lift. Yes, it was the right thing to do, if you could do it, but not by growing a longer and longer waiting list, because the longer the list, the more people living life on the sidewalks.

He pointed out that other big, complicated cities—New York and Boston, for example—did not have significant percentages of their unhoused populations living unsheltered, much less a majority, like San Francisco.

On June 14, 2022, he got unanimous buy-in from his colleagues to an ordinance that proclaimed: “It shall be the policy of the City to offer to every person experiencing homelessness in San Francisco a safe place to sleep.”

Breed signed the ordinance on June 24, and it became San Francisco law.

The policy did not say where the safe sleeping would occur, nor give the specifics of what sort of situation counted as a “safe place to sleep,” the board wanting to encourage flexibility, to evaluate new models and get the best thinking about the challenge San Francisco was experiencing.

There were two problems with the board’s approach.

First, when the policy was adopted, the board didn’t know what it would cost to accomplish what it said it wanted to do.

Second, HSH, the lead agency on homelessness, was not nearly as interested in the problem of unsheltered homelessness as it was in the holy grail of providing permanent supportive housing for the unhoused. HSH was of the “housing first” school, and in its spending it prioritized housing over shelter.

The board directed HSH to prepare “an implementation plan” that would end unsheltered homelessness in 36 months. HSH was to look at the many different models for sheltering and housing the homeless, figure out what was cost-effective, and get a plan organized for the board no later than the end of 2022.

It took HSH nearly half a year to prepare its response: an embarrassingly threadbare document—all-in it was 23 pages—that concluded it would cost $1.45 billion to cut unsheltered homelessness to zero in three years, and that money would be on top of the roughly $650 million anticipated in the regular budget for homelessness in each of those years. (The night before its testimony, HSH revised its report to reduce its estimate by $458 million.)

A backhoe near a tent surrounded by litter in a graffiti-covered city alley.
A Department of Public Works employee prepares to bulldoze an unoccupied tent during an encampment clearing on April 25, 2023, in the Mission District in San Francisco. | David Sjostedt/The Standard | Source: David Sjostedt/The Standard

Some idea of how the report’s conclusion was going to go down came from the outside contractor who worked on the project with HSH. The contractor declined the free publicity that would come with having its name on the document’s cover page. In an email to HSH it said: “We used and compiled information provided by HSH and are producing the plan that messages what HSH has decided. Our preference is to have the materials be branded solely by HSH.”

It was a stunning estimate, adding up to overall spending (including the regular budgeted amounts)— just on homelessness and supportive housing—of more than $3.4 billion over three years.

That worked out to more than $1.1 billion per year, three-quarters of the entire city budget of Sacramento, a city with more than 500,000 residents.

When Mandelman saw the numbers, he said HSH’s report “reads more like an explanation of why we can’t end unsheltered homelessness than a roadmap for how to do so. It’s as if HSH is hoping to convince the city that ending unsheltered homelessness is impossible, so we shouldn’t bother trying.” 

That supposition was confirmed by the title of the document. Having been told by the board to prepare a plan to be implemented, HSH called its filing a “report” not a “plan” so no one would imagine that the department was actually going to undertake it. This was San Francisco, after all; even with all that money, three years was not nearly enough time to find and procure sites and build the capacity needed to do the work.

But HSH told the supervisors not to worry, it was a month away from issuing its own plan. It would be a strategic plan, not a report, one that would be bold but, unlike what Mandelman requested, achievable.

That strategic plan—whimsically named “A Home by the Bay”—showed up on April 14, and it proposed to cut unsheltered homelessness in half over the course of five years. That plan was projected to cost an additional $607 million over budgeted amounts, and HSH candidly admitted that it didn’t know where the money was going to come from, a problem given that the pandemic had left the city with a projected two-year budget deficit of more than $700 million.

HSH also did not explain how cutting unsheltered homelessness in half comported with the newly enacted city policy of offering “every person experiencing homelessness in San Francisco a safe place to sleep.”

But in the end even that didn’t matter, because just a month later, the mayor proposed her budget for HSH.

Her budget proposed to add fewer than 600 new shelter beds over two years, not enough for even 15 percent of the city’s unsheltered population.

So much for big ideas, innovation, and changing the world.

Vinny Vizgaudis, who is homeless, poses for a portrait near Division Street in San Francisco on June 1, 2023. | Benjamin Fanjoy for The Standard

A Parade of Horrible Options 

Meanwhile, the city’s attempt to get rid of the injunction had stalled. 

Having lost the stay pending appeal in front of Judge Ryu, the city asked the 9th Circuit—the court where its appeal was pending—to suspend Ryu’s injunction during the period it considered the appeal. An appellate court has that power and while it is a fairly rare occurrence, you see it sometimes in high-profile cases; particularly ones that have political overtones, or where the decision at the trial court level seems wildly out of whack.

The city’s attorneys filed their motion on April 14 and probably expected that there would be an emergency argument teed up in the next few days. But as of the second week of June, nothing had happened. The court went about scheduling arguments on the appeal itself—Aug. 23—but as for the stay, nothing.

Ryu did not have a trial scheduled in the case until April 2024; if there was no relief from the 9th Circuit, the city was going to be living under the injunction for a long time.

Moreover, in August, Judge Ryu was going to consider the coalition’s motion for a special master to enforce the injunction, and there were already on file dozens of affidavits from individuals who had observed “engagements” they said that looked a lot like the sweeps that had been enjoined.

If you were a city attorney in San Francisco with strong political skills and started to wargame how this situation could play out, you’d likely see some startlingly bad possibilities.

If the city was truly prevented from clearing any encampment (except to clean the streets), what would happen if encampments started to relocate from the Mission and the Tenderloin into other parts of the city?

Even worse, what if someone began to organize the homeless into political action? What if some political stunt pilot brought a contingent of tents—imagine a procession of 1,000 shopping carts wheeling themselves through the Wiggle into the jeweled neighborhoods of Pacific Heights and Cow Hollow and Presidio Heights?

Here was the core of the problem: if the injunction meant anything, it must mean the same thing in the neighborhoods where the politicos and tech titans live as it does in the neighborhoods—the Tenderloin, the Mission, Bayview—that have long borne the problems of homelessness.

Maybe the judges on the 9th Circuit had that very thing in mind. Maybe they looked out over the nine states that comprise the 9th Circuit—Alaska, Arizona, California, Hawaii, Idaho, Montana, Nevada, Oregon and Washington—and said, what is happening on the streets in our circuit isn’t acceptable; we have to do something to change the thinking out there.

What if their plan was to let the situation on the sidewalks of San Francisco simmer and fester and get worse and worse until the city of big ideas actually had one.

Trailers are parked at Site F on property of the San Francisco Port Commission in San Francisco on Feb 22, 2023. Site F provides shelter for more than 100 people experiencing homelessness. | Joe Dworetzky/Bay City News

 The Role of a City Attorney 

 Mark Aronchick, a Philadelphia lawyer, has had a 40-year career litigating public cases. He was City Solicitor in Philadelphia, the same position as the city attorney in San Francisco, though appointed not elected.

Aronchick has been counsel in dozens of high-profile public cases over his career including cases involving prison over-crowding, gerrymandering, public school funding, same-sex marriage, the Philadelphia soda tax, as well as a raft of cases involving challenges to the 2020 election. He teaches a course on “Law Reform Litigation” at the University of Pennsylvania Law School.

 In an interview, Aronchick compared public cases to three-dimensional combat, with multiple constituencies and stakeholders, some officially parties in the case but others in crucial yet unofficial roles.

In many cases, he said, there will be multiple nonprofit advocacy groups and coalitions, sometimes in opposition to each other, and oftentimes potentially trying to fundraise off media attention to the case.

Similarly, there may be elected officials at multiple levels of government—local, state and federal—who have direct or indirect interests in the issues and may have influence over funding streams that could be affected by a resolution.

 Even within a single government entity there can be multiple moving parts. “The government is not monolithic. Different departments sometimes have different points of view. They battle each other for turf.”

  In his eyes, a city attorney in such a case serves as something of a ringmaster, responsible not only for building the case, but also constantly looking for way to resolve the case in the public interest. “Many times, when you’re the city attorney, you’re partially the client as well, because very frequently the public officials are asking you to help make the decisions that they should be making.”

Aronchick said: “So the first instinct as a city attorney is … how can we use this litigation to achieve a public good?”

Sometimes, Aronchick says, the court is a forum for resolving the issues in a way that the parties couldn’t do on their own. When he is in a high-profile case, Aronchick says he is always looking to see if there is an opportunity to take advantage of what he calls “the genius of the federal judiciary.”

In the right situation, he says, the judge can create an environment that is “a great place to take a lot of people off the hook who for some political reason, some budget reason, or some other kind of reason, can’t totally commit,” and that allows stakeholders to explain unpopular aspects to their constituencies by saying, truthfully, that “the law required it, a Court ordered it, and the risk of an adverse ruling was greater.”

But he says, there is “no one cookie cutter thing about this;” each public case is unique.

A homeless tent encampment on Division Street at Florida Street with Salesforce Tower in the skyline in San Francisco, on Thursday, June 1, 2023. The homeless crisis in the Bay Area continues and local residents aren’t sure when and if they should be given money to those asking for it. | Benjamin Fanjoy for The Standard
A homeless tent encampment on Division Street at Florida Street with Salesforce Tower in the skyline in San Francisco on June 1, 2023. | Benjamin Fanjoy for The Standard | Source: Benjamin Fanjoy for The Standard

The Endgame 

Any analysis of public litigation asks about the endgame, and what was it here?

Chiu made clear that his goal is to get the injunction set aside.

“The end game is San Francisco needs to be able to reasonably address the crisis on our streets,” he said in the interview. “And with this preliminary injunction, it’s very challenging to do so.”

Chiu continued: “We have countless city workers working around the clock to offer significant services to individuals on our streets, offer them housing and keep our streets clean, safe, and with a sufficient path of travel for all, including individuals with disabilities … Our great hope is that we will be able to continue to do so moving forward.”

If Chiu does win, the city will presumably retain the right to sweep encampments by doling out shelter beds one by one for the dispossessed.

And with a shortage of more than 4,000 shelter beds, to give one of the shelter beds to a person being dispossessed from his or her tent would mean that someone else wouldn’t get that bed. It would be musical chairs. A zero-sum game.

That might be a victory in the abstract, but it would seem a disappointing one in light of the San Francisco law that says “it is the policy of the City to offer to every person experiencing homelessness in San Francisco a safe place to sleep.”

Winning the case would do little to advance that policy.

Under these circumstances, might Chiu consider the alternative of not winning?

In that scenario, the injunction would likely remain in place and the city would have to figure out how it could provide shelter for the thousands of unsheltered people.

To make that happen, the city attorney could use his considerable political skills to ringmaster the development of a plan that offered a safe place to sleep for all.

That is what the Board of Supervisors had expected from HSH. Not should we do this, but how do we do this?

Of course, it would not be simple. There would be a score of monumental issues to solve; key among them, where would the shelter be provided, and what sort of shelter would it be?

But Chiu would have several advantages coming at the problem. First, there would be a new sense of urgency: the city would not be preparing a report at the genial direction of the Board of Supervisors but would be facing off with a federal judge.

Second, if the plan was something that made sense, the court could make getting buy-in easier. Federal judges have a way of calling out agency heads who are protecting their turf and adding gravity to the deliberations of policymakers. And this would work both ways: the advocates might have to dampen their expectations by a dousing with the water of what is feasible.

Third, while the city attorney would work with the city agencies on the plan, he could look at what made sense independently. As in any bureaucracy, the city’s homelessness agency was not likely to look at what it might cut to reach the goal. (In its A Place for All report, HSH did not propose cutting anything from its existing annual $650 million budget; in fact, it proposed that 15 percent of the total ongoing annual operating costs should be earmarked for HSH “to expand administrative capacity.” 

Of course, standing up a program like this would be an extraordinary challenge.

But if the endgame was to use the litigation to facilitate the city’s policy of offering every person a safe space to sleep, maybe this approach would result in something better than winning the case.

This story was written by Joe Dworetzky of Bay City News.