San Francisco supervisor Dean Preston recently proposed a solution to the city's skyrocketing car theft on X: simply convince residents and tourists to never leave anything in their cars. Overnight, the post went viral, achieving national ire for so perfectly demonstrating the sclerotic, self-destructive local politics of the country. As of today, the post has been viewed over 4 million times, with just over 200 likes.

But who is this local politician, and what motivates him?

Currently, Dean Preston is a member of the San Francisco Board of Supervisors, the eleven-seat legislative body responsible for drafting and approving local laws and overseeing the city’s budget. As the supervisor for District 5, a heterogeneous ensemble of neighborhoods that includes the Haight-Ashbury, Hayes Valley and, since a redistricting process last year, the Tenderloin, Preston represents almost 70,000 San Franciscans. In his four years in office, Preston has pushed for permanent eviction moratoriums, a ban on armed retail security guards, and a pandemic-era program placing homeless people in state-funded hotel rooms, where over 100 participants died, many from overdoses, and the city paid out almost $30 million in settlements to hotel owners claiming their properties had been trashed. He is also the city’s first openly democratic socialist supervisor in over 40 years, considered a “progressive champion” by his supporters, and “a cancer to the city” by his detractors.

Above all, though, Dean Preston is a man of profound, puzzling contradictions. He’s a democratic socialist who believes “the solution to the failures of capitalism is not more capitalism,” but he is also a multimillionaire who, according to public disclosure forms, owns between $100,000 and $1 million of stock in each of Apple, Cisco, IBM, and Microsoft, and owns at least three homes worth over $1 million. He has repeatedly insisted that he “[doesn’t] own rental property,” and is “not a landlord and [has] never been one,” but his wife is part of a family LLC that owns and operates several luxury apartment buildings from which Preston presumably benefits financially. He brands himself “one of California’s leading affordable housing advocates,” but his voting record shows he has opposed tens of thousands of units of affordable housing (many more than he’s supported), often at the behest of local landlords. In many ways, he is a typical “champagne socialist” — a wealthy individual who supports policies at odds with his luxury lifestyle. Politicians and activists like Preston often prompt head-scratching. Why would someone vocally support political positions in clear tension with their personal lifestyle?

In Preston’s case, closer examination suggests that the apparent contradictions might be just that: apparent, but not actual. Many of Preston’s political positions, from his opposition to thousands of new housing projects to his continued support of ‘harm reduction’ drug policies in the face of sky-high overdose rates, seem designed to entrench San Francisco’s ‘doom loop’ status quo — one in which Preston, by most metrics, lives comfortably. In this sense, he is less a champagne socialist than what we might call a “conservative progressive,” someone who adopts nominally ‘progressive’ political positions that actually have the effect of conserving the (often failing) ecosystems in which they thrive.

Now, Preston’s announcement that he will run for re-election next year has unleashed a campaign war of epic proportions. On one side, a coalition of moderates — lead by GrowSF, a political action committee started by tech workers Steven Buss and Sachin Agarwal — has banded together to form the “Dump Dean” campaign, an anti-Preston movement that has already crowdfunded over $300,000 from almost 300 donors. On the other side, Preston has amassed crucial endorsements from well-heeled and influential colleagues, including Board of Supervisors president Aaron Peskin and former mayor Art Agnos (1). The election, slated for November 2024, will be a crucial indicator of the direction San Francisco is heading in culturally and politically. Have the city’s voters finally had enough of its conservative progressive ruling class?

The Gilded Road to Socialism

Dean Preston was born and raised in New York City, in the 1970s. He spent his childhood in Greenwich Village, where he and his family lived in a luxury apartment building owned by his parents. (Today, starting prices for units in the building range from $2.2 million to $7.5 million.) Preston went on to attend Bowdoin College in Maine, where he studied anthropology and economics. (Years later, his parents would provide a “generous gift” to Bowdoin to establish the Preston Public Interest Career Fellowship, which disburses multiple $5,000 grants each year to support the “direct service or community organizing” of students “committed to enhancing social justice.”) After completing his degree at Bowdoin, Preston moved to San Francisco, where he began law school at U.C. Hastings in 1993.

At the time, Hastings teemed with progressive lawyers-to-be, many of whom participated in the school’s civil justice clinic that “trained students to become radical lawyers.” There, Preston found his way to his apparent passion: tenant’s rights advocacy. “It was impossible to be a conscious progressive living [in San Francisco] in the 1990s and not care deeply about housing,” he explained in a 2007 interview. He began work at the Tenderloin Housing Clinic (THC) in 2000, a non-profit that offers legal services and, through city contracts, permanent supportive housing to low-income individuals in San Francisco’s beleaguered Tenderloin neighborhood. In 2008, Preston left the THC to start Tenants Together, a coalition of over 50 tenants’ rights groups across California. The coalition led the successful crusade against Prop 98, a proposal to prohibit rent control state-wide, operated a ‘know-your-rental-rights’ hotline, and connected renters with housing attorneys. 

Preston’s political career began in 2016, when he ran against then-incumbent London Breed for the District 5 seat. The race was closely fought, and Preston ultimately lost 48 to 52 percent. In 2018, after Breed became Mayor, Preston announced he was again running for the D5 seat. His campaign received glowing coverage from sympathetic journalists, who compared him to then-ascendant fellow democratic socialists like Alexandra Ocasio-Cortez. “Preston [expresses] a deep understanding of the kinds of genuinely universal social programs that neoliberal Democrats seem incapable of fathoming: free public transit, a vast expansion of public housing, and public banking,” Keith Spencer wrote in Salon. The campaign slogan — “Rethink what’s possible” — was pithy and hopeful. This time, Preston cruised to victory.

Steal From the Poor, Give to the Rich

Given that Preston is a card-carrying member of the DSA, an organization whose stated purpose is to “reject an economic order based on private profit, alienated labor, [and] gross inequalities of wealth and power,” it might be surprising to learn that as Supervisor, he has consistently prioritized the interests of wealthy ‘NIMBY’ homeowners opposed to new affordable housing developments. NIMBY Report, a group run by current and former District 5 residents, has extensively documented Preston’s remarkable hostility to new development across the city on Dean Preston’s Housing Graveyard. The numbers show that, while Preston has approved around 1,600 units of new housing, he has blocked or opposed over 49,000.

Preston often takes advantage of San Francisco’s extraordinarily restrictive zoning regulations to block these housing projects in covert ways — by asking for additional impact studies, for instance, or invoking concerns about functional design. In 2020, at the urging of a local landlord, he blocked the proposed rezoning of “The Hub,” a parcel of land around Market and Van Ness where developers planned to build thousands of affordable housing units, by calling for an “equity study” that he promised would take no longer than six months to complete. Two-and-a-half years later, the study had still not started, and The Hub remained underdeveloped. A few months later, Preston blocked a proposed rezoning of an empty lot on Grove Street by arguing that the houses would pose fire safety concerns. (The SF Fire Department had not validated these concerns, and Preston expressed no interest in discussing them with one of the project’s sponsors, a retired SFFD captain). As Steven Buss of GrowSF tells me, this dogged opposition to new development ultimately benefits “multimillionaire landowners who pay very little in taxes and recognize that Preston is the guy who’s going to prevent change from happening to the neighborhood they like.”

On drug and homeless policy, Preston has largely kowtowed to his other core group of supporters — DSA-types who want free supportive housing for all, and more harm-reduction drug policy in the face of the city’s increasingly deadly opioid epidemic. During the pandemic, Preston successfully pushed through a permanent moratorium on evictions due to ‘covid-related’ nonpayment of rent, a legal codification of his early declarations that his district was an ‘eviction-free’ zone. He also championed the Shelter-in-Place hotel program, which from April 2020 to December 2022 placed over 3,700 homeless people in hotel rooms to reduce the spread of Covid. As mentioned above, over 100 participants died and the city was on the hook for tens of millions in damaged property settlements paid to hotel owners. Many program staff reported needing “ongoing counseling” for the trauma induced by repeatedly intervening in overdoses, and finding tenants dead. When they applied for funding for mental health support, the city turned them down.

On crime, Preston has largely trod the path paved by Chesa Boudin, SF’s recalled progressive DA. This past May, after a man was shot and killed while shoplifting goods at Walgreens, Preston announced legislation which would ban retail security guards from even unholstering their weapons. (As critics pointed out, this policy, in conjunction with California’s reclassification of certain felony theft offenses as misdemeanors, would effectively remove any deterrent to shoplifting.) When asked on video by Erica Sandberg, a SF-based independent journalist, whether he supported arresting and prosecuting fentanyl dealers in the Tenderloin, he refused to answer. In May, when Breed announced a pilot program allowing law enforcement to intervene when drug users publicly engage in behavior that poses danger to themselves or others, Preston called the proposal “reactionary, cruel, and counterproductive.”

Why do Preston and other SF conservative progressives push for reduced penalties for non-violent crime in the face of widespread shoplifting and carjacking in the city? Why do they continue to support harm-reduction policies that research increasingly shows are ineffective at reducing fentanyl-related deaths? I put these questions to Tom Wolf, a recovery advocate and former addict who was once homeless in the Tenderloin. Wolf believes the prevailing narrative pushed by harm-reduction advocates — roughly, that criminalizing drug use and related crime exacerbates, rather than reduces, the death and misery associated with addiction — is based on stale data from the 1980s crack epidemic. Back then, he says, it may have been the case that many users were also selling drugs to survive, and that arresting and slapping them with long prison sentences was cruel and unhelpful. “But all the data now suggests that organized drug dealers funded by cartels are selling their product on the streets of San Francisco.” And the product they’re selling — fentanyl, a synthetic opioid 50 times stronger than heroin — leads to a much deadlier form of addiction than crack. Hence the skyrocketing overdose fatality rate in San Francisco.

If many conservative progressives like Preston have not updated their priors on harm reduction, it may be because they are largely insulated from the appalling human costs of their political positions. Wolf tells me that some D5 locals he knows say Preston spends most of his time on his ranch in Mendocino County, far from the District. While I couldn’t confirm this, it wouldn’t surprise me; Susan Dyer Reynolds has found that, in addition to his $2.7 million SF home and his $1.5 million home on Long Island, Preston has purchased at least two properties in Mendocino County — including a 567-acre nature preserve he recently sold to the co-founder of an engineering firm that has received almost $10 million in contract fees from the City of San Francisco in the past seven years. 

In any event, it would be best to hear from Preston himself, or from one of his supporters, about how he reconciles the DSA’s stated hatred of the “parasitic 1% [that] hoards their wealth at the expense of the 99%,” with his own outsized personal fortune. Unfortunately, no one from his office returned my multiple requests for comment, nor did anyone from the pro-Preston Public Defender’s office, nor did anyone from the SF DSA. Preston once said, in an interview with Jacobin, that he is “always blown away when [he] sees people giving political speeches, talking about housing as a human right, and [then] working with developers and corporate landlords the next day.” For once, I must agree.

— Sanjana Friedman

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1. Details of Preston’s current campaign finances are not yet publicly available. In the 2020 election, he received over $443,000 in campaign contributions.