More money is pouring into the high-profile District 5 supervisor race than any other supervisor race in town, and even Elon Musk and Bernie Sanders have weighed in on the showdown between Supervisor Dean Preston and challenger Bilal Mahmood.

In the leadup to the 2019 election, when Dean Preston was running against newly elected Mayor London Breed’s appointee Vallie Brown, we wrote that the race was “capturing little attention.” Oh, how things have changed.

Preston has now served nearly five years in office as the sole Democratic Socialist on the board, and has become a lightning rod for criticism from tech’s biggest bigwigs. Tesla CEO Elon Musk said Preston “should go to prison” (though the above-promised $100,000 donation to beat Preston never came through), and Y Combinator president Garry Tan told Preston to “Die slow motherfucker” (a threat he also lodged at other progressive supervisors).  The tech and YIMBY sets have singled Preston out for taxes on landlords and claims that he’s stifled housing development, allege he’s curtailed law enforcement powers, and for his Gaza ceasefire resolution they say has little to do with the governance of San Francisco.

Yet Preston has won the support of liberal lions like Bernie Sanders and Nancy Pelosi. And he’s built himself a firewall of progressive support for his COVID-era eviction bans and hotels for the homeless efforts, fight for free Muni fare, and relentless advocacy for rent control.

So Preston has himself a credible challenger in tech executive Bilal Mahmood for the District 5 seat. They and the other candidates in this race have managed to make this the priciest supervisor 2024 race in town (as of press time for this article, at least). The D5 race has now seen a total of $1.75 million in contributions, more than twice as much as has been raised in the D7 race, to represent the district that includes Haight-Ashbury, Hayes Valley, the Western Addition, and thanks to 2022 redistricting, now the Tenderloin.

“While a lot of people have been trashing this city non-stop, I have been working to make this a better community,” Preston said at a September League of Women Voters debate (seen below). “I have dedicated my life to making sure that this is a place where not just the wealthy can thrive.”

“We have to double down on housing affordability and anti-displacement work. It’s what I’ve been doing for decades and what I’ll continue to do as supervisor,” he added. “While we see Fox News attacking us constantly, I am busy stopping evictions, housing homeless families, and delivering for my constituents.”

Mahmood takes issue with Preston’s results. “I walk past the open-air drug market every night when I go home on McAlister, as I live a block away,” he said at that same debate. “It affects the people who are suffering from overdoses on our streets, it affects the children who have to walk by during the day, and it affects the families at night that aren’t able to go outside because of the gun violence.”

“If we don’t address this crisis, we’re not creating the safe conditions for all levels of our society here,” Mahood concluded.

And he really hopes to take on Preston in the housing issue.

“Housing is the crux of the District 5 debate in this campaign,” Mahmood said at that candidate forum. “It’s the Number One issue we hear from residents every day, and it’s because we are the slowest city to approve housing in the entire state, and possibly the entire country.”

“It’s not progressive, it’s embarrassing to have a housing project approved so slowly,” according to Mahmood.

Preston countered that night that “I voted to approve 30,000 units of housing, 86% of it affordable, and I’ve been especially focused on housing for working San Franciscans. Look across the district and you’ll see what we are doing. One hundred and sixty units of affordable housing in the Haight, the biggest housing development in a generation in the Haight-Ashbury.”

“We convinced the state to build housing on the DMV lot, we’ll be having hundreds of units of affordable housing there. 180 Jones, the Kelsey, 650 Divisadero, we are building affordable housing,” he insisted.

Homelessness is of course also front and center in this race.

“It seems like every election year there’s a push to criminalize homelessness, and now that effort is supercharged by Trump’s Supreme Court,” Preston said at the forum. He touted a “21% decrease in unsheltered homelessness in our district. That didn’t just happen.” He said it happened because of 114 units opened to unsheltered  people at the Gotham Hotel, opening the Oasis Hotel to homeless families, and his work at preventing evictions.

But Mahmood iterated that the status quo has not been working. “I do not support tent sweeps,” he said at the forum. “We don’t have a money problem in addressing homelessness, we have a bureaucracy and execution problem.”

Preston has lived in the district 28 years, Mahmood moved there in 2023. And Mahmood had a somewhat embarrassing scandal when SFist reported he was falsely claiming to be a neuroscientist, despite having an otherwise very good resume that did not need embellishing.

Yet Mahmood may benefit from the work of a political action committee calling itself the “Dump Dean PAC.” That PAC has raised and spent nearly $300,000 on mailers and online ads to promote Mahmood and disparage Preston. Nearly all of that money was raised in July 2023, and more than half of it came from current or former Y Combinator employees. Mahmood, it should be noted, once had his startup funded by Y Combinator.

There are a couple other candidates running for the District 5 supervisor seat; 2022 school board recall activist Autumn Looijen, and marketing executive Scotty Jacobs. Both are running hard anti-Preston campaigns.

So Preston probably needs to win this thing outright in first-choice votes, because it’s hard to imagine that any of the other candidates’ voters would choose Preston as a second-choice in ranked-choice voting. But District 5 is no stranger to elections that take several days to resolve, and the new landscape of redistricting makes picking a winner less predictable here.

Related: PAC Opposing Dean Preston Gets Half of Its Donations From Firm Whose CEO Posted ‘Die Slow’ Tweet [SFist]

Images: (Left) Dean2024, (Right) BilalMahmood