After 17 years wielding power and influence on the San Francisco Board of Supervisors, Aaron Peskin is facing a rather existential moment:

Has this famously liberal city moved too far right to embrace an old-school progressive like him for mayor?

Peskin, a slight man of 60 with a full beard and glasses, has spent his political career fighting for liberal causes. He’s taken on large corporations, wringing substantial money from them to bolster community services. He’s a vocal proponent of rent control and neighborhood preservation. As a recovering alcoholic, he thinks the city’s homeless issues should be addressed through a mix of compassion, affordable housing and services, rather than a punitive approach utilizing encampment sweeps and criminal citations.

Despite his experience, Peskin entered the mayor’s contest against incumbent Mayor London Breed and three other Democrats — venture capitalist and former interim Mayor Mark Farrell, Levi Strauss heir and nonprofit executive Daniel Lurie, and fellow Supervisor Asha Safaí — as an underdog.

Peskin joined the race in April, several months after Breed and the other three competitors had started campaigning. That put him at a financial disadvantage in a mayoral election shaping up as one of the most expensive in San Francisco history.

But even more significant: Peskin entered the race as the only candidate running on a progressive agenda, putting him at odds with the rising chorus of voters and tech titans who want to see a more hard-core approach to the sprawling tent encampments and drumbeat of retail and property crimes that have eroded their sense of a safe, functional city.

In recent decades, it hasn’t been unusual for San Francisco to elect mayors who are centrist Democrats alongside a more progressive Board of Supervisors. But the tech money flooding into the race, combined with frustrations over the city’s slow recovery from the COVID-19 pandemic, has many voters questioning progressive policies and the wisdom of a city that governs with a bleeding heart.

Myriad parents were furious that the city’s schools were closed for more than a year during COVID — longer than most in the country. The remote learning persisted even as the school board engaged in a divisive effort to rename a third of the city’s public schools whose existing names, critics asserted, honored historical figures associated with slavery or oppression of women or “who otherwise significantly diminished the opportunities of those amongst us to the right to life, liberty, and the pursuit of happiness.”

Outrage over the progressive agenda fueled the recall of three school board members in February 2022. Four months later, voters also recalled then-Dist. Atty. Chesa Boudin, a leading reform advocate whose progressive policies on sentencing and incarceration were derided by opponents as a threat to public safety.

Last March, San Francisco made national headlines when voters approved a pair of ballot measures that Breed had championed to broaden police surveillance powers and impose drug treatment mandates for certain welfare recipients. That same night, a slate of moderate candidates took control of the governing body of the local Democratic Party.

Although the five leading candidates for mayor are Democrats, all but Peskin now fall in that moderate camp. Breed, in particular, has tacked right on issues such as homelessness and crime over the last year.

Peskin celebrates the distinction, saying that he joined the race to keep San Francisco a “beacon” for the artists, creatives, immigrants and LGBTQ+ pioneers who’ve shaped the city’s culture for decades, and that he fights for working-class people to ensure they can afford living in the city.

“Don’t get me wrong, I think that one of the most important things that any government does is to make people safe,” Peskin said. “But, you know, that’s all the other candidates are talking about. They’re not talking about also making it safe and welcoming.”

Supervisor Aaron Peskin says he joined the mayoral race to keep San Francisco a “beacon” for the artists, creatives, immigrants and LGBTQ+ pioneers who have shaped the city’s culture.

(Jeff Chiu / Associated Press)

Peskin has targeted Breed from the start of his campaign, arguing that her leadership is incoherent and dismissing her recent crackdown on homelessness as a cynical political ploy.

“She actually embraced the Fox News narrative about San Francisco, rather than standing up and defending this city and embracing and strengthening our policies of compassion and of getting things done,” he told The Times.

Breed has countered that compassion has its limits, and that the city needs to take a tougher stance with homeless people who have refused shelter or won’t seek treatment for drug addiction.

During a July mayoral debate hosted by the local firefighters union, Breed said her decision to get tough on the homelessness crisis may not be popular but was necessary to propel San Francisco forward.

“We have had to move from a compassionate city to a city of accountability,” she said.

Peskin said he is focused on leading San Francisco beyond the “doom loop” narrative that has dogged the city nationally for much of the last four years and into its recovery era.

If elected mayor, he’s promised to prioritize low-income housing and expand rent control. On homelessness, he wants to open more treatment facilities and expand shelter capacity, rather than continue the encampment sweeps that Breed has pushed over the last two months.

Peskin said he knows something about recovery.

In 2021, Peskin entered treatment for problem drinking amid allegations that he had joined a government meeting inebriated. The episode unleashed broader complaints that Peskin for years had bullied colleagues and lower-level staff, and that people feared retaliation if they reported his behavior.

Peskin ultimately apologized. And after spending the initial weeks after the uproar in shame, he said he’s now grateful for the wake-up call and is more than three years sober.

“I always thought that my job was to care for the community, and I never realized that people actually cared about my well-being,” he said. “The amount of support and love and encouragement that I’ve gotten from the most unlikely places and people has been just remarkably heartening.”

But even as Peskin touts his personal and professional journey, local polls show him trailing Breed, Farrell and Lurie in the city’s ranked-choice voting system. All three have made tough positions on property crime, fentanyl dealing and homelessness a centerpiece of their campaigns.

Whereas Breed, Farrell and Lurie are getting financial support from tech executives and wealthy business owners, Peskin touts his campaign as a grassroots effort fueled by working-class people. His endorsements include left-leaning LGBTQ+ and tenant rights organizations, labor unions and progressive politicians including former Mayor Art Agnos, former Supervisor Jane Kim and former state Sen. Mark Leno.

“Aaron Peskin was built for public service,” Agnos said. “What we have today are tech multibillionaires. Tech multibillionaires who live like monarchs, and now we are seeing they’re trying to rule San Francisco like they were monarchs.”

“I think San Francisco has always led on the social issues,” said Kim, who unsuccessfully ran against Breed in 2018. “Where we struggle and fight as progressives has been on the economic agenda, and who benefits economically in this city. Is it the ultra-wealthy and the billionaires, or is it our working class and our low-income workers? And that’s the fight that Aaron is leading on.”

Supervisor Aaron Peskin, right, says he wants to address homelessness by expanding treatment facilities and shelter capacity. He opposes the aggressive encampment sweeps launched by Mayor London Breed, center.

(Eric Risberg / Associated Press)

Along with staunch supporters, Peskin has accumulated fierce critics during his years in office — particularly around housing.

Peskin represents some of the city’s most historic neighborhoods, including North Beach, Chinatown, Fisherman’s Wharf and downtown’s Financial District. He often distinguishes himself as someone who sticks up for neighborhood identity — what some consider a dog whistle for “NIMBYism,” a colloquial term for opposition to large multifamily housing projects or other unwelcome development. He has resisted efforts to amend zoning rules for certain neighborhoods to allow for denser housing.

“Peskin would be an unbelievable step backwards,” said Laura Foote, executive director of the advocacy coalition YIMBY Action, a housing organization that endorsed Breed. “We need to protect these people in our communities from the ever-escalating cost of housing, and that means building more.”

San Francisco has one of the longest housing approval processes in the country, and is tens of thousands of units shy of its state-mandated production goals.

Breed has called for more housing development across all income levels in San Francisco as rental costs skyrocket and the median home price exceeds $1 million. Farrell, Safaí and Lurie have also endorsed denser housing, though to varying degrees and in some cases only in certain neighborhoods.

Peskin rejects the idea that he is anti-housing as a “developer-funded narrative.” But he also argues that it’s possible to build more housing “without turning Ocean Beach into Miami Beach.”

The disagreement over development highlights another layer of San Francisco’s drift toward the political center, with more leaders coming out in favor of multifamily housing projects despite outcry from progressive groups concerned about gentrification and neighborhood changes.

State Sen. Scott Wiener (D-San Francisco), who has authored some of the state’s strongest housing production laws, has criticized Peskin’s devotion to the “existing broken housing structure.”

Wiener, who has endorsed Breed, complimented Peskin as skilled and “incredibly smart.” But he also warned that Peskin’s brand of progressivism would set San Francisco back.

“San Franciscans are quite progressive. But there is a strain among some people — I think it’s a minority, but some people — where they equate progressivism to having no change,” Wiener said. “A city that isn’t changing is a city that is dying.”

Peskin has been willing, at times, to buck the progressive label. He has supported laws to retain police staffing, and recently told The Times he supports a controversial November ballot measure, Proposition 36, that would roll back a 2014 voter-approved law that turned some nonviolent drug and theft felonies into misdemeanors. Critics of the initiative, including Wiener and Gov. Gavin Newsom, say it would mark a return to an era of mass incarceration.

Peskin uses those examples to argue that he can be compassionate while also being practical.

“I’ve always thought the root of progressive is progress,” Peskin said, “and progress is actually getting things done.”