As conservative groups and opponents have put up heaps of money to unseat District 5 Supervisor Dean Preston, the city’s only elected Democratic Socialist, an odd political metamorphosis has unfolded.
Bilal Mahmood, a District 5 challenger backed by the opposition money, nonetheless sees value in labeling himself as the most progressive of them all.
At other times, however, he talks more like a law and order conservative.
Political analysts said that oscillating between the two is both a measure of Mahmood’s views, and a recognition of the political reality that District 5 is one of the city’s most progressive districts. Take the March election: When a solid majority of the city voted in favor of Mayor London Breed’s Proposition E, limiting police oversight, District 5 was in opposition.
District 5 has “set the tone for progressivism for the last half century,” said political consultant David Ho. Since district-level elections were reinstated in 2000, District 5 residents elected two Green Party candidates through 2012, and twice put Preston in office. Breed, who held the seat from 2013 to 2018, was an “outlier,” Ho said.
This reality, political analysts said, may explain Mahmood’s sometimes progressive bent. This separates him from two other challengers, school board recall initiator Autumn Looijen and newcomer Scotty Jacobs, who have remained stalwart in calling for more deportations and more carceral approaches to crime.
Mahmood has received backing from big-tech names like Chris Larsen and Garry Tan, angel investor Ron Conway and his family, and moderate to conservative city figures like Josephine Zhao and Laurance Lem Lee. As of January, a political committee to remove Preston from office had pulled in nearly $300,000; up-to-date contribution amounts will be available at the end of July.
At the same time, Mahmood is, according to a weekly Q&A by Mission Local, often in agreement with Preston. Out of 23 weeks of questions, he has agreed with Preston or shared similar views 10 times.
Like Preston, he supports safe drug-consumption sites, calls for better and expanded drug treatment options, and voted against Prop. F, the mayor’s successful ballot measure to require drug screening for welfare recipients.
When the mayor proposed a curfew for convenience stores in the Tenderloin, Preston and Mahmood were the only two candidates who had reservations about the idea. Mahmood called it a “temporary crutch” and both called for more comprehensive plans to address street conditions. (Preston worked out adjustments to the proposal, and Mahmood told Mission Local he is fine with the outcome.)
At a recent campaign event, Mahmood called for “doubling down on our progressive values,” and added that it is “progressive to build housing at all levels: affordable, middle income, market rate.” He talks of “compromise” and “collaboration,” and he was an advocate for climate justice before launching his political campaign this year.
At other times, Mahmood’s conservative guns are blazing. At the same event, he zealously called for arresting drug dealers, to applause from his audience. He supported Prop. E on the March ballot to reduce oversight of the police, despite concerns he had about other clauses in the ballot measure, like easing restrictions on police chases.
“I think that it’s gonna be hard for Bilal to get to the left of Dean Preston, but he has to make himself acceptable to the progressive voters in the community,” said political consultant Jim Ross, adding that, with ranked-choice voting, candidates “want to be as broadly appealing to as many voters as possible.”
Mahmood isn’t as far right as his District 5 competitors, at the end of the day; he says he supports progressive ideas like public banking, social housing and a ceasefire in Gaza. Still, he “would fall pretty solidly in the conservative side of things,” Ross said, when it comes to the main indicators: Regulation of industry, taxation or development.
Housing: Where the rubber meets the road
Mahmood says the “primary contrast” between himself and Preston is over housing. And on that topic, Mahmood, a YIMBY, defines himself as a true progressive by national standards. He compares himself to left-wing politicians like Democratic Socialist and Assemblymember Alex Lee, or New York representative Alexandria Ocasio-Cortez. The similarities? They, too, are YIMBYs, he said.
“The question of, what does it mean to be progressive on housing? It is progressive to be ‘yes in my backyard,’” Mahmood said. “So I think that’s where I draw contrast to where I don’t feel [Preston] is progressive enough.”
Preston, for his part, called the argument “silly.” He noted his record pushing for affordable housing, keeping tenants from being evicted, and stronger rent control.
“To frame the deregulation of market rate housing — that is not affordable to working class people in San Francisco — to frame that as a progressive position is really a triumph of propaganda,” Preston said. He added that he supports upzoning, but he prioritizes protecting the working class and vulnerable, an objectionable stance to YIMBYs.
What’s more, political consultant Jim Stearns noted that Mahmood has failed to take “a really strong YIMBY stance on stuff.”
Stearns points to Mahmood’s wavering position on Parcel K, a contentious piece of land in Hayes Valley long slated for affordable housing. Parcel K, is adjacent to Patricia’s Green and has been temporarily used as an outdoor cinema, gym, and pop-up food site.
When asked whether the city should proceed with its housing plans for Parcel K, Preston is unequivocal, noting that its interim use has been successful and popular with the community, but adding, “I’m committed to delivering affordable housing there.”
Mahmood took less committal position: He suggested “building adjacent to Parcel K,” or “building affordable housing on the parcel, but with an atrium on the ground floor,” but then appeared to suggest dropping the issue.
“This parcel has been debated for more than 20 years — it’s time we focus on progress over parcels. Let’s focus instead on where we can build affordable housing fastest,” he wrote.
Progressive, wishy-washy or simply unformed?
Some, like Stearns, see Mahmood’s contradictions as a reluctance to take a stance.
Others see Mahmood as a classic case of a candidate finding their place. Ho said candidates diving into such “post pandemic pop-up activism,” like Mahmood, are still trying to find their political identity.
“Oftentimes, people manufacture a narrative,” Ho said. “Candidates like Bilal come and go, and if they win, they’ll probably end up evolving into a political identity that suits them best.”
Mahmood dismisses the charge that he is trying to straddle both sides; he not only sees his challenge to Preston as a “progressive on progressive fight” — and his YIMBY values, he says, make him the true progressive in the race.
And on other issues, like dealing with illicit drug markets, he sees his favored Drug Market Intervention approach as taking components of progressive and moderate frameworks that can’t be “pigeonholed.” For example, he calls for arrests of drug dealers, but does not believe in arresting drug users.
To be or not to be a progressive
Political consultants agreed that if District 5 were to change out of progressive hands, it could be a strong bellwether for progressives’ power citywide. But “If the progressives can’t hold District 5, they’re not going to be able to maintain a very slim majority on the Board of Supervisors,” Ho said.
The meaning of “progressive,” however, has become malleable, allowing candidates throughout the political spectrum to claim it as their own.
“I think it’s just an obsession with the word, and it’s an obsession with the idea that there’s some moral superiority to being a progressive,” said Stearns. “So let’s just twist the words around and make it fit. So I’m now, magically, the progressive — but that doesn’t work in real life.”
Mahmood is not the only one seeking the “progressive” label.
At times, even Looijen uses similar language, and told Mission Local she wants the city to achieve its “progressive values.”
But her record tells another story: Looijen has been supported by well-known conservative figures in San Francisco politics; Republican investor David Sacks backed and funded the school board recall she led, and she is one of few candidates endorsed in this election by the police union. She calls for police intervention to resolve the issues in the Tenderloin, along with compelled drug treatment and chipping away at the city’s sanctuary protections.
Looijen said she has accepted “that does make you a little further to the right” than her competitors.
“What I want to do is lay the foundation of safety and stability in the Tenderloin,” Looijen said. “And then, on top of that, we can build our progressive paradise.”
Preston said it is not believable for Mahmood or Looijen to claim progressive values, considering the large amounts of money both have accepted from conservative interests and the issues they have focused on in their campaigns.
“Whether someone agrees or disagrees with all my policies,” Preston said, “I don’t think that it is really in dispute that I am an unapologetically progressive politician advancing unapologetically progressive policies to benefit those who are struggling the most and to stand up to big money.”
The ‘mushy middle’
But the strategy of anointing oneself as a progressive, if only semantically, is a worthwhile one to win voters, especially in a truly left-leaning enclave like District 5, analyst Ross agreed.
“He’s sort of trying to be all things to all people,” Stearns said of Mahmood. “It’s a really hard place to run from because politics is about making choices, and I don’t think you can just mush your way into a majority.”
But that may be the path Mahmood chooses.
Take his responses to Mission Local’s question on the U.S. Supreme Court Grants Pass v. Johnson ruling about criminalizing homeless encampments, even when no shelter beds are available.
Preston called the ruling unconscionable. Looijen said the city must still act compassionately, regardless of the ruling. Jacobs said he supports sweeps if people refuse shelter. Allen Jones expressed the futility of the ruling.
Mahmood said we must “focus on addressing the root of the problem.” He did not answer the question.


Look at the candidate’s record. Look at their actions. Easy to say you are a”neuroscientist” when you are not. Easy to say you are a “common sense” candidate who wants “clean safe streets.” You have got to be a good listener with a keen brain AND a policy wonk AND an expert and nuanced legislator in a city as diverse and dense as San Francisco, and, even more importantly, in a district like D5.
YIMBYs vascillate between bashing progressivism and trying to capture the progressive flag. Mahmood is a shill and there is little question which camp he would belong if elected. Looijen isn’t even worth speaking of as a serious contender as she struggles to respond coherently to ML’s weekly questions.
Mahmood is running for Supervisor in District 5, where a large majority of residents are tenants. Dean Preston, the current District Supervisor, has a long career and is well known as an advocate for renters and tenant rights. THC, Tenants Toghether, Tenants RIghts bootcamps, and his legislative and policy work on the Board of Supervisors. Preston also owns a house, which detractors consider a grievous failure that should cancel out all the work he has done for tenants. Not at all incidentally, Mahmood and his supporters have absolutely no problem with the home ownership Farrell, Lurie, Supervisor Stefani, and I’m gonna guess every mayor prior to London Breed – not are they fazed by the monstrous wealth of the key “investors” behind the AstroTurf movement to hoard political power as a crucial asset in their portfolio.
In an attempt to legitimize himself, Mahmood opted to rent an apartment rather than purchase a condominium so he could gain residency in District 5 to enable his candidacy for district supervisor. Mahmood is playing a game here. Yes, he is a renter – but he rents an apartment at 50 Jones Street, one of the recent gentrification projects on the edge of the Tenderloin. Virtually every housed resident in the neighborhood is a renter. They live in subsidized permanently affordable housing, in single room occupancy (SRO) hotels with faulty elevators and other health and safety problems, in studio or one-bedroom apartments either alone or more frequently with roommates and even their whole family plus another family. As a rule, whether recent arrivals as immigrants or refugees or as long-term tenants, Tenderloin residents are low or very low income, burdened by the rent for their cramped living space, and food insecure. The Mayor’s Office of Housing and Community Development reports that more than 25 percent of Tenderloin households are linguistically isolated, defined as no member of the household over 14 speaks English without difficulty.
Bilal Mahmood is none of those. He is wealthy and has undergraduate and graduate degrees from the two of the most prestigious Anglophone universities in the world.
I’m no fan of Dean but these other candidates are deeply disconnected from our district in the most obvious ways, especially Mahmood. D5 deserves so much better!
Candidate Mahmood believes in free market solutions. Bilal Mahmood believes in public/private partnerships where corporations are unaccountable to residents and human beings who live in communities. Nothing about candidate Mahmood is progressive. The public has seen how fast and loose Mahmood plays with campaign finance laws and with Ethics.
Where’s Bilal? This D5er sees Dean all the time, in the community talking to folks, attending events, riding MUNI, etc. Haven’t spotted Bilal once.
Under Dean Presons time , both the Tenderloin and Lower Polk Street has only worsened.
It is beyond time for change
The drugs cartels are winning
Both affordable housing , jobs , etc and law enforcement is needed .
Until thr drug supply and demand are controlled , this area will remain a drug death camp
Progessives have only caused harm here ,
How about someone who cares, and is willing to help out both the people on the street and the neighborhood ,
The Lower Polk Street area is ruined and dangerous .
Very tragic
Being a “progressive “ and having law and order is necessary
Never forget: San Francisco’s population is comprised of over 60% tenants. For many decades a majority of San Franciscans have fought for tenant protections from displacement, illegal evictions and the trickery of real estate speculators and greedy landlords. San Francisco’s real estate values, income disparities and eviction crises have only worsened in the last decade; a powerful driver of homelessness in SF. The YIMBYs have NEVER ONCE joined with tenants. At every turn, YIMBYs are silent on illegal evictions, rent increases, displacement and injustice to black, brown, elderly and low income workers…….a consistent and striking distinction that exposes the central YIMBY lies of “legalizing” and “trickle down” housing. You are either pro-tenant and for the protection of existing affordable housing to fight displacement, or you are anti tenant. Equally revealing: market rate lobbyist and chief YIMBY Corey Smith’s flatulent and spurious lawsuit against Preston is further evidence of YIMBY hypocrisy. Same goes for last week’s veto proof vote at the full Board of Supervisors where YIMBY lap dogs Matt Dorsey and Joel Engardio opposed Preston’s sensible resolution in support of the statewide “Justice for Renters” legislation which woukd repeal Costa Hawkins. YIMBY opposes this pragmatic legislation and is spreading scary and completely false talking points about Costa Hawkins repeal. Furthermore: Bilal Mahmood claims to be a tenant. So does Autumn Looijen and Scotty Jacobs: they also each own property although they don’t speak openly about that, while they demonize Preston for living in the home he purchased with his wife in the 1990s. Point being: ask any of these 3 new arrivals to tenant rich and progressive D5 exactly what and how they will protect tenants, elders and working families who rent. There lies the truth.
I’m relieved to have 2 real common sense candidates run: Autumn & Scotty.
I think San Franciscans are tired of the “progressive ideology”
– just fix the sidewalks , and address crime, clean the streets. These are issues that incumbent ignores.
Sidewalk repair is the responsibility of the property owner whose building the sidewalk is in front of. You can open a 311 request so the city can notify the owner(s).
Street cleaning is the responsibility of Public Works. You can email Director Carla Short if you want your street cleaned. PW is under the mayor’s office, so supervisors really don’t have any control over their work schedules or diligence. I know Valle Brown said she used to go around picking up trash everywhere in D5, so you could try contacting her.
….”just fix the sidewalks, and address crime, clean the streets.” These are city wide issues that the current incumbent Mayor ignores. There. I fixed it for you CS. Let’s ride!