Bilal Mahmood and Dean Preston clash over money in SF District 5 race

Preston views Mahmood as aligned with well-heeled and often controversial tech-industry leaders firehosing cash to oust him.

Mahmood balks at binaries like “moderate” or “progressive” — though, for the record, he identifies as progressive — and believes the residents of District 5 simply want a leader with solutions.

But regardless of how ideologically or behaviorally aligned he is with tech-industry giants angling to rid The City of Preston, Mahmood is poised to benefit from their money — and money has quickly become a sore subject in the race.

To Preston, Mahmood is already linked to big players such as Garry Tan, the CEO of Y Combinator, and Musk, the owner of social-media platform X, who have used their platforms and financial resources to oppose progressives in San Francisco.

That’s nothing new in San Francisco, but how they’ve done it is particularly volatile.

Tan sparked controversy recently when he appropriated a Tupac lyric and suggested that eight members of the Board of Supervisors — including Preston — “die slow.” Musk wantonly suggested that Preston “should go to prison.”

“They’re engaged in a takeover, or trying to engage in a takeover of The City,” Preston told The Examiner. “I would characterize it as a hostile takeover of The City.”

But Preston’s opponent in his bid for a second term representing District 5 — which includes the Haight-Ashbury, Tenderloin and Hayes Valley neighborhoods — isn’t Tan or Musk. It’s Mahmood.

Mahmood, the son of immigrants from Pakistan, insists that he’s independent of San Francisco’s political machinery.

“In San Francisco, politicians are fixated on making this a battle about us versus them, good guy and bad guy, and they’re always trying to divide us and establish division,” said Mahmood, who ran unsuccessfully in a special election for the state Assembly in 2022.

Mahmood, a tech entrepreneur himself, argued that Preston has benefitted from the tech industry and risks alienating its employees.

“He wants to continue to demonize 30% of the people who live here, when we need to be building bridges so that 100% of The City can benefit from the people he wants to demonize,” Mahmood said.

Instead of focusing on political factions, Mahmood said, he’s interested in making progress on San Francisco’s chronic issues, such as reining in drug dealing in the Tenderloin and alleviating the staffing crisis in the public-safety and health departments.

“Dean wants to make this a narrative in that vein because he is unpopular in his district,” Mahmood said. “I’ve been knocking the neighborhood since I announced, and he’s not unpopular necessarily just because of his ideology. He’s unpopular because of failing to deliver.”

Mahmood publicly apologized after his separate campaign for a seat on the Democratic County Central Committee — for which he is running simultaneously — sent out a mailer stamped with the logo of his supervisorial candidacy.

DCCC campaigns are not subject to donation and expenditure limits — but those funds are not allowed to be used directly for campaigns for supervisor.

It’s not unusual for candidates to seek a seat on the DCCC and another elected position simultaneously, and more than a few are doing so this year. But the line between the two is clear to everyone who runs for two positions, Preston said.

“He did something that’s clearly illegal in actually crossing that line,” Preston said. “That doesn’t happen accidentally, but even if it did ... it just makes a mockery of the campaign finance system if you can do that.”

Mahmood quickly reported his own campaign to The City’s Ethics Commission, publicly apologizing and explaining that the mislabeled mailer was an honest error by campaign staff.

Preston and Mahmood have each opted into The City’s public financing program, which will offer up to about $250,000 in matching funds to Board of Supervisors candidates who agree to limit their expenditures to $350,000 throughout the campaign.

Mahmood has already raised $225,450 for the DCCC campaign, more than twice what any other DCCC candidate has raked in.

The top contributors thus far each chipped in $20,000. They are Jessica Livingston, a co-founder of Y Combinator; Jeremy Liew, a partner at venture-capital firm Lightspeed; and Ripple CEO Chris Larsen. (Tan has given $5,000).

GrowSF, a PAC founded by two tech-industry workers to support moderate candidates, announced in 2023 — more than a year before the election — a new political action committee formed for the sole purpose of ousting Preston.

Ultimately, Preston believes his message will resonate more with District 5 residents than those spending large sums to defeat him.

“They’re trying to sell something that most people don’t buy in San Francisco, so they have to spend enormous amounts of money to do that and convince people that up is down and down is up,” Preston said.

But Mahmood is not alone in questioning Preston’s record, particularly regarding housing.

“He’s lying about his record, and the people will see that on the ground, things aren’t changing,” Mahmood said.

He levels the same criticism at Preston’s leadership on the fentanyl crisis, which Mahmood said he would tackle in part by advocating for drug-intervention strategies backed by the U.S. Department of Justice.

But because Preston hasn’t delivered results, Mahmood says the incumbent is leaning on divisive tactics.

“Any politician who’s worried about their numbers or actual outcomes on the ground will then try to pivot to us-versus-them,” Mahmood said.

Preston points to his connections in the district where he’s lived for more than 25 years. As an attorney, he focused on protecting tenants from evictions, he said.

But Preston questions Mahmood’s offer of change.

“The guy is like the embodiment of the status quo of The City,” Preston said. He said Mahmood is “campaigning as if he is change and running against someone who is in sync with the district.”

Preston — the only card-carrying democratic socialist on the Board of Supervisors — understands the animus people have against city government, and he says he’s right there with them.

“I don’t think there’s anyone in elected office that is pushing harder for change against entrenched and powerful interests in our city, and I think people see that,” Preston said.

In a citywide race, Preston acknowledges, it’s difficult to be heavily outspent. But he said he believes he can outpace the money against him with his feet. He’s had the benefit of running two previous campaigns for supervisor and knocking on “every door in the district,” he said, and he plans to do so again.

He questioned Mahmood’s ties to the community, noting Mahmood only recently moved there.

Mahmood moved to The Tenderloin less than a year ago, but he has lived in San Francisco for about a decade and has spent recent years working on community projects such as rebuilding a Chinatown community center’s computer lab.

“I’ve had a range of experience of helping at the state, local and federal level because that’s the type of experience we need to tackle the biggest challenges that face our city from affordable rent to climate change to homelessness, to housing, to hate crimes, to violence,” Mahmood said.