As the Democratic Party abandons the working class and progressive policy, a unique opportunity rises for socialists nationwide. People are looking for an alternative to the obstructionist two-party system which serves only the richest among us. Achieving electoral change is perhaps most easily realized in urban liberal strongholds, where, with few Republican opponents to contend with, socialists can focus their fire on moderate Democratic candidates while presenting truly progressive, revolutionary alternatives. Once in office, however, the socialist threat to the ruling class is as evident as ever, and the elite will do anything to oust socialists from power and prevent meaningful change.
San Francisco socialists faced this problem head-on in the latest election where two DSA members ran for seats on the Board of Supervisors. While their platforms and ideals overlapped, incumbent Dean Preston’s slim loss and newcomer Jackie Fielder’s resounding win present an invaluable case study on how to run socialists for office effectively and the barriers to keeping them in office after they win.
Mr. Preston Goes to City Hall
Dean Preston was a tenant rights lawyer for over a decade before running for San Francisco’s District 5 supervisor seat, doing so amidst the swell of progressive support erupting in 2016. Preston lost the 2016 election (48% to London Breed’s 52%) but formed a team of experienced strategists and volunteers through his campaign, including meeting Jen Snyder at a Bernie Sanders rally. Snyder would help found DSA’s San Francisco chapter (DSA SF) that year, become Preston’s campaign manager and then Chief of Staff once in office, and then later co-founded Red Bridge Strategies, an electoral consulting firm, with Avery Yu in 2021. Preston’s defeat did not stop them, and they shortly began work on a salvo of revolutionary ballot measures.
Preston himself authored 2018’s Proposition F, a ballot measure to instate the nation’s first right-to-counsel for tenants facing evictions. That same year, he campaigned alongside DSA SF for Proposition C, which proposed to tax businesses earning over $50 million per year to fund housing and homelessness services. Both measures passed, beginning a chain of victories for working class people in San Francisco. The Prop F campaign went largely unopposed in what Snyder describes as a “sneak attack win.”
The credit, however, was swiftly stolen by newly elected Mayor London Breed and her appointee to District 5, Supervisor Vallie Brown. Dean Preston and DSA SF were conspicuously excluded from a news conference featuring the pair celebrating Prop F’s passing. DSA SF protested the event with bullhorn and flyers, refusing to take such a rewrite of history sitting down. This attempted snub demonstrates how Democrats (and Republicans, should we succeed outside urban areas) will not only erase socialist contributions to society, but take credit for them, especially if we do not have our own information campaigns celebrating our work.
Then, fresh off the victories of Propositions F and C, Preston, Snyder, and DSA SF would get an earlier-than-expected opportunity to mount another candidate campaign in a special election to fill Breed’s seat after her election as Mayor.
Preston ran against the mayor’s handpicked candidate, Vallie Brown, for the District 5 Board of Supervisors seat—the seat he lost to Breed just three years before. Brown was a moderate Democrat with name recognition and “significant roots in the community,” Snyder said. After becoming mayor, Breed appointed Brown to fill out her term. In response, Preston’s campaign ran a grassroots, field-heavy campaign with massive support from DSA and huge mobilizations of volunteer door knockers—a strategy DSA SF, Preston, and Fielder continue to replicate.
Vallie Brown’s candidacy took a hit late in the campaign when SF Weekly reported that, 25 years earlier, she had evicted a building’s worth of Black tenants in the Fillmore, a neighborhood of District 5. Preston, the tenant rights lawyer, could not have asked for a more perfect story to boost his campaign. As Snyder narrates, “With very little institutional support and a total outsider… we won.” Their narrow victory in the special election set the stage for 2020’s general election. Preston bested Vallie Brown once more, this time by eleven percentage points.
Housing the People
From the beginning of Preston’s tenure in office, he demonstrated his commitment to realizing his campaign promises. Snyder emphasizes, “Dean being this housing champion, it’s a lot bigger than what it sounds like. He’s truly one of the most transformative, amazing fighters for the working class that you could ever ask for.” As the pandemic descended, Preston introduced legislation to the Board of Supervisors banning evictions of tenants unable to pay due to Covid-related economic issues. During his 2020 re-election campaign, Dean and the DSA campaigned for and passed Prop I, a measure to double the transfer tax on real estate sales over $10 million to fund back rent payment for those affected by Covid as well as social housing.
Snyder sees these victories, however, as “the final straw” for the real estate developers and landlords. Preston was instrumental in preventing landlords’ attempts to evict the victims of the 2020 economic shutdown and raise the rents on new tenants. “The amount of money he has cost the super-rich is incredible,” she said. Dean Preston has stopped developers and landlords from gaining untold millions, functionally implementing massive wealth redistribution through taxes on the rich that are then used to provide tenants affordable housing.
The super-rich could not ignore these developments, but they would have to endure years before the next election while Preston pursued his policies. In 2022, Preston, Red Bridge, and DSA SF campaigned for and passed Propositions M and H. Prop M imposed a tax on vacant units in larger multi-unit buildings, incentivizing landlords to rent empty units at more affordable rates. Proposition H would harmonize San Francisco elections, placing them in even years. Voter turnout was historically higher in even years, and moving SF’s elections to them would help make the voice of the people heard. Mayor Breed dubbed this successful effort to increase voter turnout a democratic socialist power grab, lifting the mask off the Democratic Party’s face, if only for a moment.
These policies set the stage for GrowSF’s $300,000 “Dump Dean” smear campaign, which GrowSF touted as “grassroots,” despite pooling funds from only 300 donors and lacking any policy planks or ideals to strive for.
The campaign focused on undermining Preston’s housing record, but could only do so by misrepresenting the facts and falsely claiming Preston had blocked the construction of affordable housing and other progressive measures in city hall. Although founded on baseless claims, the smear campaign’s “repetition, intensity, and volume made the difference,” Snyder continues. When presented with such a high volume of misinformation, “people who are fairly low-information believe it.”
Combined with 2022’s redistricting, which removed the progressive Inner Sunset neighborhood from District 5 and coupled the low-turnout Tenderloin neighborhood to the new map, Preston lost. The final round of ranked-choice voting saw a return to 2016’s percentages: 47% for Preston to Mahmood’s 53%.
DSA vote share calculated as the endorsed candidates’s share of round 1 votes. San Francisco Board of Supervisor elections are conducted using instant run-off voting; in subsequent rounds, votes for trailing candidates were redistributed in line with their voters’ ranked preferences. Map by Adam Kaiser.
Jackie Fielder’s Rising Star
A few districts over, Jackie Fielder’s campaign triumphed: in isolation, it looks like socialists are ascendant. Economic inequality is becoming more stark by the day, and neither major party is offering substantive policy solutions. San Francisco has a GDP of $250 billion yet it fails to house its 8,300 residents experiencing homelessness. The city hosts yearly conventions on “innovation” while people go without housing, medical treatment, and food in the streets.
“Having someone acknowledge that reality is refreshing for people,” said a staff member on Fielder’s campaign who requested anonymity. “Jackie has been homeless. She’s young, and the Mission trends younger,” they said of one of District 9’s three neighborhoods. “She understands the reality of being that age.”
During the field campaign, Fielder and her team focused on her personal character. “There isn’t enough time during the two minutes at the door to focus on policy details.” Instead, what resonated with those answering the door was that she was “independent of corporate and state interests,” as her campaign staff member noted, and that she wants to keep the streets clean, buses funded, and ensure schools get clean drinking water.
Fielder presents herself as a no-nonsense everyperson, stating in an interview with Jacobin: “As a service worker, educator, and community organizer who, despite graduating from Stanford with two degrees and working as a lecturer at a state university, I am someone who’s experienced housing insecurity myself. The rent is too damn high, and the planet is too damn hot. It’s time for new leadership that is not afraid to make sweeping changes and talk about inequality and actually put money where its mouth is.”
The district supervisor campaign was not Fielder’s first. Fielder ran unsuccessfully against Scott Wiener for State Senator in 2020. Though she did not win that race, she maintained the relationships she built with local community organizations that helped her win her 2024 campaign.
“What she has done in [District] Nine is unify a lot of different community groups, community organizing, individuals who have been alienated. The relationships of these organizations with each other have been strengthened,” said Fielder’s campaign staff member. “Jackie is a lightning rod,” they continued. “The pandemic and capitalism have broken up these connective tissues in our communities and Jackie was a huge part in bringing these groups together.” From women’s groups to tenants unions, Berniecrats to queer clubs, the California Nurses Association to climate coalitions, Jackie Fielder became a powerful bridge between these ideologically-aligned yet unacquainted organizations. “Jackie understands more fundamentally the importance of community organizing,” they added. “DSA needs to operate in the world and in our communities.”
Fielder wound up winning in a crowded field, beating out six other candidates in a ranked-choice election and prevailing against Democratic Party-endorsed Trevor Chandler with just shy of 60% of the vote in the final round.
More Money, More Problems
“Jackie’s win is what you get when you don’t have interference from billionaires,” said Jen Snyder, who was a strategist for both campaigns. “When you [get to] have the conversations with people, and you tell them that you want to give them a better life and redistribute money – that’s what you get.”
Both Fielder and Preston ran on a platform that emphasized their independence from corporate and state interests as well as support for rent-relief, affordable housing, public transit, and improving social safety nets, but Preston’s campaign faced an added obstacle: money.
Any one of Preston’s accomplishments (a residential vacancy tax, a ban on pandemic evictions, increased taxes on real estate sales over $10 million, or the right to counsel for tenants facing eviction) alone would have been enough to draw the ire of wealthy real estate owners. With them combined, Preston became a target for the ruling class who believed it was unacceptable that he remain in office.
San Francisco Board of Supervisor races have strict contribution limits of $500 per eligible contributor, but political action committees (PACs) can flood electoral races with essentially unlimited amounts of additional spending so long as they do not directly coordinate with specific candidates. San Francisco’s most notorious PAC, GrowSF, a conservative PAC funded by big tech, has inundated San Franciscans with misleading mailers and online ads every election cycle since 2020—long before the 2024 election cycle started. Though undermining progressive candidates for years, they officially launched their “Dump Dean” campaign in 2024, spending more than $300,000 (collected from only 300+ donors) over the course of the election cycle to unseat him.
It mattered little who won the seat, as local tech investor and GrowSF supporter Jason Calacanis tweeted as early as 2023: “Who out there is willing to run against @DeanPreston? We will give you unlimited support to create a safer San Francisco & remove this incompetent fool. @GrowSF go!” They had no policy objective, no plan for a better San Francisco, only a desire to oust a champion of workers’ rights. “They would have gone with anyone who wasn’t Dean,” said Snyder. That someone would turn out to be Bilal Mahmood.
Mahmood worked as a national policy advisor for the Department of Commerce under the Obama administration and was co-founder and CEO of analytics software company ClearBrain, before it was acquired for an undisclosed sum. He ran an unsuccessful bid for the California state assembly in 2022, in which he supported the recall of San Francisco’s Board of Education, which GrowSF attacked for opting for virtual learning during the COVID-19 pandemic.
Mahmood’s resume is otherwise startlingly empty. Even GrowSF’s own founder cofounder, Sachin Agarwal, had little faith in him. “Sachin was very concerned that Bilal was a weak candidate,” said District 5 candidate Autumn Looijen, who Agarwal urged to drop out, so as not to split the vote.
Rather than supporting Mahmood, the overwhelming majority of GrowSF’s funds therefore went into their smear campaign. Combined with Mahmood’s $229,399 in private campaign funds raised, big tech spent nearly $530,000 to unseat Preston. It bears repeating that these are local, not state or national races. Fewer than 30,000 votes were cast in District 5. In contrast, GrowSF spent only $55,031 on independent expenditures to support Trevor Chandler, Fielder’s main opponent in District 9, and raised no funds for the remaining supervisor races. Big Tech targeted Preston, and Preston alone.
Losses and Gains
Jackie’s victory is resounding. Getting over 60% of the vote is an astounding achievement, and proof that working class issues win. If they did not, there would be no reason for PACs like GrowSF to throw hundreds of thousands of dollars in local campaigns to unseat them. At the same time, these two races together demonstrate how we must always act as though we’re one step away from losing.
“We on the Left need to understand that it is all of our responsibility that none of our elected socialists go through this same thing in the same way,” Snyder said, referring to Preston’s loss. “It’s so critical that we defend the people that we put into office. Dean’s inherent popularity with the Left, Progressives, and Labor in SF clouded some of the realities that were going on.”
While we are gaining a supervisor with an innate talent for community organizing, Snyder continues, “we’re losing the most prolific tenants rights champion in the entire state and all the wisdom that comes with that. I’m so glad we’ve got Jackie in there, she’s gonna be great at carrying the torch and we’ll certainly be by her side, the whole Dean Team. It’s a major blow to working class people.”
We cannot afford to leave elections to election season. Elected socialists need support from us year-round: social media networks to showcase their wins, letters to the editor, op-eds. Snyder insists “person to person is still the best way to build a movement.” Voters need to be informed that “this person gave me a free attorney, this person gave me my rent relief, this person is here and has my back.”
We can only continue to win, however, if we build a people-powered information machine willing to spend every day countering misinformation and informing voters how socialists have materially improved their lives. This cannot be isolated to the digital realm. Door knocking and mailers will be required when it is not campaign season. Protests at city hall must become as frequent as its efforts to roll back Preston’s and the DSA’s gains. Supervisors and newspapers must be inundated with our own complaints and letters. Union and tenant strikes must coordinate with growing interconnectivity, with figures like Jackie Fielder at the helm.
In the event that Fielder picks up the torch that Preston will be leaving behind, she will no doubt face a renewed attack from big money donors who know from experience what messaging can convince San Franciscans to vote against their own interest. The superrich will mislead voters with blank check smear campaigns and faux-Left candidates, flooding us with false information. We must be ready to combat it at every turn. It is imperative that we study our defeat and ensure it doesn’t happen again.
Jackie Fielder, a young indigenous and Mexican woman, is tailor-made fit to the district she will represent. She will need to strengthen the community ties she has built even further, nurture them, and be ready to wield them against the all but certain misinformation campaign awaiting her in 2028. Every victory for the working class she wins must be laid out for voters to see. The coming years will see economic inequality spike, and when it does, when the working class cries out for change, we must be ready and loud with the answer.