Dump Dean or embrace him? Sizing up the most polarizing man in city politics

In late September, the wealthiest man in the world waded into San Francisco politics. Apparently upset by a measure being mulled by the Board of Supervisors that would restrict the use of weapons by private security guards, Elon Musk took direct aim at its author. 

“Dean Preston should go to prison,” Musk wrote on X to his 174 million followers.

Musk also pledged to contribute $100,000 to unseat Preston—San Francisco’s lone Democratic Socialist and a tenants rights lawyer—in the November 2024 election, doubling Y Combinator founder Garry Tan’s offer of a $50,000 donation to oust Preston.  

Though Musk has yet to pony up those six figures, the episode illustrated just how well-known, or perhaps infamous, Preston has become—not just in San Francisco but far beyond. Indeed, “Dump Dean” has become less of a call to oust a single supervisor and more of a meme—essentially, among the incumbent’s more vociferous online opponents, a synonym for fixing San Francisco itself.

To supporters, Preston is a principled lawmaker who has dedicated his entire career to keeping vulnerable people in their homes. During the pandemic, he pushed to extend a residential eviction moratorium and repurpose vacant hotels as shelter for unhoused residents. He was the driving force behind the Gaza cease-fire resolution in January and a 2022 ballot measure shifting mayoral races from odd-numbered years to higher turnout presidential years, which progressives hoped would work to their benefit. He recently introduced a no-turn-on-red bill, and he’s been a strong supporter of car-free Hayes Street. 

To detractors, however, Preston is an ideologue more interested in lobbing rhetorical Molotov cocktails than in the nitty-gritty of constituent services. His interest in halting Muni’s fare increases by definition starves the beleaguered transit agency of necessary funding. His anti-incarceration stance leaves him open to the accusation that he’s actively abetting the fentanyl crisis and indifferent to his district’s top concerns. And his insistence on affordable housing makes him the city’s No. 1 NIMBY.

As a wealthy man who lives in San Francisco’s tony Alamo Square, Preston has faced endless criticism of the “champagne socialist” stripe, along with accusations of hypocrisy when he opposes market-rate housing and police overtime. Consequently, he faces a tough reelection battle in November: Some $300,000 has been raised already to defeat him, by far the most well-funded campaign against any incumbent.

To be sure, Preston has cultivated a reputation during his five years on the Board of Supervisors as a crusader. As the security-guard weapons measure showed, he is unafraid to tackle hot-button issues. He drafted the legislation after 24-year-old Banko Brown was shot and killed by a security guard at a downtown San Francisco Walgreens last April for allegedly stealing $15 worth of candy. The guard was arrested, but no charges were filed. Crowds protested, and elected officials sought, unsuccessfully, to have the state attorney general step in. 

"Property should never be placed above human life, and our laws should be crystal-clear on that," Preston said at the time. 

Musk’s anger aside, Preston’s measure proved uncontroversial among his colleagues on the board. It passed 11-0, and Mayor London Breed signed it into law.  

Breed is facing a tough election fight in November as well. Although Supervisor Aaron Peskin is widely expected to enter the race, at present every major mayoral candidate is grouped among the city’s moderates. This makes Preston San Francisco’s most visible progressive at a time when the entire progressive project is under sustained assault.

Preston is at the center of the city’s political zeitgeist. And depending on how you feel about the state of San Francisco today, you probably either love him or hate him.

Born in 1969 in New York’s Greenwich Village, Preston grew up with two siblings in a grand, prewar apartment building opposite Washington Square, right near New York University. His mother, Linda, was a native New Yorker. His father, Kenneth, born Hans Albert Pressburger in Stuttgart, Germany, in 1931, fled the Nazis with his parents, arriving in New York in 1941. They founded a medical device distribution company, J. A. Preston, that was later assigned patents for rehabilitative instruments like a hand dynamometer to test grip strength.

Preston’s education reflects a privileged upbringing. He graduated from New York’s prestigious Horace Mann School, an Ivy League preparatory academy where tuition today runs about $62,000 per year. Preston then enrolled at Bowdoin College, a small private school in Maine where he later met his wife, Jenckyn Goosby. He graduated magna cum laude in the Class of ’91 with a double major in anthropology and economics. 

Two years after graduating from Bowdoin, Preston moved to San Francisco with Goosby, who is part of a locally prominent Black family. Her grandfather, Dr. Zuretti Goosby, a dentist in private practice, was the first Black member of the San Francisco Board of Education, appointed in 1967. During his 12-year tenure, “Zoo” rose to become president of that body, helping shepherd the city’s schools out of the era of official racial segregation. 

Preston got his law degree from the University of California Hastings in 1996. Initially attracted to international human rights, Preston became a tenants rights lawyer.

He worked for seven years at the Tenderloin Housing Clinic, a taxpayer-funded supportive housing nonprofit that has long assisted marginal populations but whose properties have more recently been the site of fatal overdoses. “What appealed to me,” Preston said to Beyond Chron in 2007, “was doing cases that were about people—rather than paper.”

In 2008, Preston left the housing clinic and founded Tenants Together, which describes itself as California’s only statewide renters’ rights organization and which was instrumental in securing a right to an attorney for all San Franciscans facing eviction. It has also fought abuses of the Ellis Act, a controversial California law that enables landlords to clear a building of its tenants before putting it on the market.

Meanwhile, the elder Prestons eventually followed Dean and his two siblings west, relocating to San Francisco. They bought a unit at 1333 Jones St., a mid-century apartment tower otherwise known as The Comstock. Linda Preston died in 2009, Kenneth in 2021. A year later, the two-bedroom co-op sold for $2.6 million.

Preston and his wife own a single-family home in Alamo Square, where they live with their two daughters, and which Zillow estimates to be worth about $2.5 million—roughly three times what they paid for it in 1999. In 2022 and 2023 financial disclosure statements, Preston listed ownership in four blue-chip tech companies, including Apple and Cisco Systems, of between $100,001 and $1 million each. Separately, a Goosby family trust owns several buildings in San Francisco, but since its membership is private, it is unclear whether Jenckyn Goosby receives a portion of any rental income.

Opponents have pointed to his in-laws’ trust as proof that Preston is a closet landlord, an accusation he denies, adding that he has been part of a tenant lawyers’ organization that explicitly forbids members from owning rental property.

“I've never been a landlord in my entire life,” he said. “I've never even represented a landlord.”

In person, Preston is soft-spoken, with a tendency toward defensiveness. More than casting oratorical thunderbolts down from Marxist Mount Olympus, he waded into the minutiae of city policy while pausing to greet supporters who interrupted to say hello during a recent interview at a Peet’s near City Hall. 

Online, though, he has been belligerent toward constituents, with a tendency to assign blame for multifaceted issues on capitalism. He has been called a mansplainer. Shortly after Musk tweeted for his imprisonment, he left the platform altogether.

One’s opinion about Preston’s five years in office may be ascertained with a simple word-association exercise. If the term “socialism” evokes Copenhagen’s ample bike lanes and free health care in your mind, you probably like Dean Preston. If it suggests Caracas’ hyperinflation and breakdown of civil order, you’re maybe not such a fan. 

Perhaps more than his personality, it’s Preston’s affiliation with the 90,000-member strong Democratic Socialists of America that strongly colors opinions about him. To some, the organization’s anti-Zionist stance is disqualifying right out of the gate. To others, it’s a sign that a well-off Gen Xer grasps millennial and Gen Z anxieties about the future. Preston is undeterred.

“Obviously, the majority of people in my district did not think of this as a problem,” he said of his DSA affiliation. “Because I ran very clearly as a Democratic Socialist and was elected first time by a narrow margin, and then second time by a double-digit margin.”

“There's nothing offensive about being a Democratic Socialist,” said Peskin, the president of the Board of Supervisors. “Bernie Sanders was a viable candidate for president of the United States. Matter of fact, there's something kind of interesting about having that diverse voice on the board.”

By way of highlighting his opponents’ misplaced zeal, Preston points to one of his core achievements: the Covid-era eviction moratorium. Implemented on March 16, 2020, it was intended to remain in effect for as long as the Mayor’s Proclamation of Local Emergency was in place and, after Preston pushed for a 60-day extension, lasted through September 2023.

“I've been working for 20 years on tenants’ rights,” Preston said. “But if you had asked me five years ago whether I thought in my lifetime that we would see a time when evictions were effectively banned for a period of years, and we set up massive rent relief programs …?”

He let the question mark hang in the air without answering it, adding that without the moratorium, San Francisco would have had tens of thousands of evictions by now. And to anyone who reflexively blames lefties as the city’s catch-all boogeymen, he offered a boogeyman of his own: capitalism. Downtown looks the way it does, Preston believes, because corporations all but abandoned it.

“The problems of a once-in-a-century pandemic have been strategically blamed on progressives,” he said.

District 5 is an oddly mapped entity, shaped like a dragon in flight or maybe a turtle with a rear-facing gun mounted to its shell. Encompassing Japantown, Hayes Valley, parts of Lower Pacific Heights and Upper and Lower Haight, it also contains City Hall, the historically Black Fillmore District and the corner of Golden Gate Park where Kezar Stadium stands.

It looks a lot different than it did during Preston’s last race, too. In a pitched battle that involved sessions that went late into the night and accusations of interference from both sides, the city’s Redistricting Commission axed most of the Tenderloin from District 6 and grafted it onto District 5. Cole Valley and parts of the Inner Sunset were then drawn out, tilting an already progressive district further leftward, ostensibly to the benefit of Preston and Supervisor Matt Dorsey. 

Coincidentally, D5 is also Mayor London Breed’s turf. Preston holds the unusual distinction of representing his chief political antagonist’s childhood home—the Plaza East public housing—along with her current residence and her place of work. 

Yet over the course of three elections, Preston has continuously increased his standing with D5 voters. He ran against Breed in 2016 and lost 53% to 47%. After Breed became mayor and appointed former legislative aide Vallie Brown to her seat, Preston ran against Brown in a 2019 special election and unseated her by fewer than 200 votes. The following year, Preston defeated Brown 55% to 45% in a rematch for a full term. (If he wins in November, he will be termed out in 2029.)

These days, Preston’s relationship with Breed is, by all accounts, nonexistent. He says he and his team have been frozen out.

“For whatever reason, the mayor has decided that trying to actively undermine our office at every opportunity and stoke that division is politically advantageous to her,” he said. “And that includes even things where we are probably in full agreement.”

Indeed, Preston's and the mayor’s offices negotiated separately with Safeway after the grocery chain announced it would close its Fillmore District location. Each side claims credit for winning a one-year reprieve, although only after the mayor somewhat flippantly referred residents of the historically underserved neighborhood to an as-yet-unbuilt Trader Joe’s in Hayes Valley.

The Mayor’s Office did not respond to requests for comment on this story. And while the hostility is certainly a two-way street—Preston frequently jumps at the chance to needle Breed over affordable housing—other allies largely confirmed his account. According to Peskin, torpedoing Breed’s hand-picked successor out of office was Preston’s original sin, and something no amount of shuttle diplomacy can fix. But it’s deeper than that.

“Willie hated me,” Peskin said of former Mayor Willie Brown, now a close friend. “But I cannot think of any other case where a mayor hated on a supervisor as personally as London's antipathy for Preston.” 

Supervisor Hillary Ronen, another Preston ally, concurred. “I’ve never seen anything like it. That’s what I’ll say to that,” she said. 

Dorsey, who is frequently on the opposite side as Preston, would not discuss the mayor’s relationships with other supervisors. But, he said, in spite of disagreements over police staffing and housing production, his working relationship with Preston remains strong.

“I genuinely like Dean, and I have a lot of respect for him and his team,” Dorsey said. “I've always appreciated his professionalism and his collegiality. He does not personalize disagreements. And [he’s] able to put disagreements aside for the good of the district.” 

Preston also has something of a reputation as a lone wolf. 

“The longer I’m there, the more nothing’s black-and-white and everything’s nuanced,” Ronen said. “He’s often been the lone no vote.”

Referring to the city’s $14 billion budget, she said finding an outcome that’s acceptable to the mayor and all 11 supervisors required a lot of compromise. “I have to be collegial in order to have a compromise that I can live with,” Ronen said, “and Dean is not willing to do that.”

By his own admission, Preston doesn’t fraternize with fellow supervisors. The demands of the job are 24/7, so when he does have free time, he spends it with his family or with friends outside of politics. One housing advocate called him a total dadcore guy who “maxes out at two beers at a party.” 

This also means his allies can’t lean on a sense of chumminess. Preston reviews legislation before signing on; ideological affinity isn’t some override button a colleague can push to get a quick yes. 

“Dean is not a supervisor or a person who is part of a clique,” Peskin said. “He's not a bro. He's not a back-slapper. What you see is what you get.”

Being a lone wolf can also mean getting singled out for criticism.

Christin Evans, the owner of Booksmith and a longtime board member of the Haight Ashbury Merchants Association, pointed to an episode where Preston took flak for saying the best way to avoid a smash-and-grab—getting “bipped”—is not to leave valuables visible. 

“They were saying he was blaming the victims, and that’s so not true,” she said. “The police themselves have been putting out this message of ‘Don’t be a victim of crime’ for decades.” 

Indeed, Preston is a lightning rod like almost no one else in San Francisco. A YIMBY-affiliated site records the number of housing units it claims Preston has blocked but doesn’t track other lawmakers. The pinned tweet on his inactive X account that directs his followers to BlueSky gave way to a thread in which he’s called a communist and a friend of antisemites.

Steven Buss, a director of GrowSF, spared no words about Preston. “My impression of him is that, like most Twitter trolls, he’s a lot of sound and fury online. But when you see them in person, he’s that mousy, shy, nervous kind,” Buss said. “I can’t speak to his character, but he certainly fits the archetype of the Twitter troll.” 

Among the city’s tech elite, Garry Tan is cheerleading the incumbent’s defeat, most notably in a deleted tweet that called for the “slow” deaths of Preston and six other sitting supervisors. Tan is a major donor to GrowSF, a feisty PAC that has morphed from a YIMBY-aligned group into an organization that can appear focused on its “Dump Dean” initiative to the exclusion of almost anything else, listing no fewer than 31 reasons to oust the supervisor. 

Through a spokesperson, Tan declined to comment for this article. During the second half of 2023, GrowSF raised $289,000 for the sole purpose of unseating Preston. That’s four times the $72,000 it marshaled during the same period to defeat another progressive incumbent, Supervisor Connie Chan, and roughly twice as much as the pro-Preston side has raised. GrowSF has not yet endorsed a candidate in District 5, although it has endorsed Preston's main opponent Bilal Mahmood in his quest for a seat on the Democratic County Central Committee.

Mahmood—an opponent of Proposition F’s mandate to screen public assistance recipients for drug use, a critic of District Attorney Brooke Jenkins and certainly to the left of former interim mayor and current hopeful Mark Farrell—sees the race as a parallel to the 2022 Assembly race in which he took third place, leaving progressive former Supervisor David Campos to duke it out with the incrementally more moderate incumbent Matt Haney, who eventually won.

“They were both progressive,” Mahmood said. “The only difference was one of them was pro-housing and one was not.”

In the wake of Tan’s tweet, Preston professed that he’s more optimistic about his chances of winning than he was before. He has laid out an ambitious vision for his second term, including more subsidized housing, safe consumption sites and a push for a public bank. 

“All of that is doable in San Francisco,” he said. “But it's really hard to see how we scale up on our own without a mayor that’s a partner.” 

By that logic, unseating Breed is the key to improving San Francisco’s parlous state. Before November, though, comes the March 5 primary. Supervisors aren’t on the ballot, but members of the obscure-but-powerful body known as the Democratic County Central Committee are. 

A moderate slate is challenging the reigning progressives, and the winning side will then dole out coveted party endorsements that could prove decisive in key races this fall. Gloria Berry is a member of the progressive slate who is running for reelection. A Black woman who had experienced homelessness for a three-year period, she admits she was initially skeptical of Preston’s candidacy.

“Back when he ran against London Breed for supervisor, I probably was with the community on ‘Why does this white man need to be supervisor in a district that includes the Fillmore?’” she said. “I felt the same way as a lot of people: Support the Black woman.” 

Berry was turned off to Vallie Brown after allegations surfaced that Brown had evicted tenants from a building she’d jointly purchased decades before. 

“Due to my experience of living in the Fillmore in an apartment building with six Black families, and all of us being evicted for a condo conversion, it kind of hit a nerve,” she said. “Mr. Preston’s fight for tenants’ rights, period, is what drew me to listening to him.”

However, Berry is no longer a resident of District 5. She was priced out, she said, and now lives in the Bayview.

This story has been updated to clarify GrowSF's role in the District 5 race.