When District 5 Supervisor Bilal Mahmood unseated incumbent democratic socialist Dean Preston in 2024, San Francisco leftists mourned.
Though Mahmood called himself a progressive, many were skeptical — he had the backing of a tech-funded PAC in 2024 that spent $300,000 against Preston, and was part of coordinated takeovers that year of the Board of Supervisors and the San Francisco Democratic Party.
With Mahmood, those efforts won. The newcomer gained a seat on the local party chapter, and ousted the city’s lone democratic socialist official when he was elected to oversee District 5.
But in his 15 months in office, Mahmood has bucked expectations. He has become a less reliable vote for the board’s moderate bloc, and more outspoken about issues like blocking immigration enforcement and taxing the rich. Some of his past backers are now questioning their support.
“If you donated to Bilal Mahmoud [sic], you should call him and tell him he needs to stop doing the exact opposite of what was supposed to happen when he defeated Dean Preston,” wrote Y Combinator CEO Garry Tan in a February post, along with a screenshot of a Mission Local article detailing Mahmood’s support for a proposed “Overpaid CEO” tax.
Tan grumbled about Mahmood’s stance and said the supervisor “was supposed to help tech but isn’t.” The tech CEO gave $50,000 to the heavily funded “Dump Dean” PAC to oust Preston in 2024, and had called on the public to join him when he gave $5,000 to Mahmood earlier that year.
A longtime Mahmood supporter, Tan once wrote on X that the city’s progressives should “die slow motherfuckers” and said that “candidates like [Mahmood] are the only way we get out of the mess we are in.” His polemics have others piling on, like Kane Hsieh, a tech investor who once donated to Mahmood but has now turned on him.
In February, Hsieh blasted Mahmood’s plans for creating ICE-free zones in San Francisco to his 35,000 followers on X. “What is the rationale for @sfgov paying to shelter felony drug traffickers from federal law enforcement?” Hsieh wrote.
The money, however, is not following Tan’s dictum. Steven Buss, who co-founded GrowSF, the moderate political group where Tan once served on the board and that endorsed Mahmood’s election, spending $300,000 against Preston, still supports him.
Buss disagreed with Mahmood’s stance on the CEO tax and said they would “never see eye-to-eye on 100 percent” of issues. But he said he was still “proud” of the campaign to oust Preston from office and said Mahmood overall was “doing all the right things” and making “all the right votes.”
Chris Larsen, one of San Francisco’s most politically active billionaires and the co-founder of cryptocurrency company Ripple, echoed Buss. He accepts that he and Mahmood won’t always agree, but engages with him on the issues. He said he still supports Mahmood’s work as a balanced and “practical” leader, but disagreed on his stance taxing wealthy corporations, known as Proposition D.
“His support of [Prop.] D is disappointing,” Larsen said, calling the tax a “net loser” for the city in a text. “I think he’s getting the balance btw saving government worker positions (progressive) and not sacrificing private sector jobs (moderate) wrong.”
Like Larsen, Mahmood’s more moderate supporters are unlikely to let him forget where they stand.
Last month, when the Democratic County Central Committee voted on whether to endorse the proposed CEO tax, Mahmood, who won a seat in 2024, again ruffled feathers when he joined the body’s few progressives in voting for it.
Forrest Liu, an attack dog in moderate political circles and a Tan acolyte, approached the dais and stared directly at Mahmood, according to multiple people present. “Look at me, look at me, supervisor,” he said. The body’s chair, Nancy Tung, demanded Liu sit down.
Mahmood has gone against the moderate line various times in the last year and change:
- Support of Prop. D, the “Overpaid CEO” tax
- Creation of ICE-free zones
- Hearing into Waymo for system failure
- Investigation into GEO Group with Supervisor Jackie Fielder
- Attendance at anti-ICE protests
- Expansion of immigrant legal defense at the public defender’s office
- Outspoken on Palestine, including condemning a humanitarian mission visitors’ deportation and attendance at a Jewish Voice for Peace anti-Zionist seder
Emma Hare, legislative aide for Supervisor Myrna Melgar, said Mahmood’s stances show he is “breaking the mold of moderate and progressive in a way that is refreshing for everyday San Franciscans.”
Mahmood, for his part, calls himself a “pragmatic progressive,” a middle-of-the-road leader who has been consistent in his stances.
“For too long San Franciscans feel like they’ve been given a choice [where they] have to choose one side or the other,” Mahmood said. He maintains “respectful dialogue” with most of his supporters, even if they disagree at times.
‘Thoughtful and transparent’ to some, toxic to others
Even some progressives welcome his policy positions. Former city supervisor Jane Kim, a colleague of Mahmood’s on the Democratic County Central Committee, said she did not support his campaign for office but said he has taken “some very progressive positions, and has been consistent to the values he ran on.” Kim called Mahmood “thoughtful and transparent.”
Sunny Angulo, who worked as Kim’s legislative aide then former Supervisor Aaron Peskin’s, said she was “impressed” with Mahmood calling out Mayor Daniel Lurie’s office of housing over a “lost” $5 million in funds for affordable housing, reported by Mission Local.
But, she said, supporting the Prop. D tax increase — like his moderate colleague Supervisor Danny Sauter — didn’t require much political lift. “The true test of whether or not people can authentically live these values is whether they’re willing to stand up to power,” Angulo said.
She called him socially progressive but still “policy moderate,” and pointed to his support for Mayor Lurie’s contentious housing upzoning plan and his plan with the mayor to reduce taxes on multimillion dollar real-estate deals.
One political observer agreed, saying that although Mahmood is “largely aligned” with moderates on housing and other issues, plenty of political observers see him as a progressive.
“A lot of people overread what he ran on and they wanted him to be a moderate,” the observer said. “He made it really clear that one thing he wanted to do was to be essentially a YIMBY on housing” and otherwise “a click to the right” of Preston. Some of Mahmood’s early backers, they said, “wanted him to be someone he’s not.”
When the supervisor called for a hearing into Waymo after the robotaxis stalled and gridlocked city streets during a recent power outage, Hsieh the tech venture capitalist accused Mahmood of “fake concern” and wrote that he was “disappointed by the cheap populism that seems to define your messaging now.”
Still, Mahmood’s name is so toxic among certain leftist circles that he is sullying an erstwhile progressive congressional candidate. Saikat Chakrabarti’s $10,000 donation to Mahmood in 2024 is frequently touted as a reason for progressives to spurn the former Alexandria Ocasio-Cortez chief of staff and go for Supervisor Connie Chan instead.
Just earlier this month, Mahmood voted with his moderate colleagues on the Board of Supervisors in favor of permanently destroying a rent-controlled unit of housing, and allowing what’s now an illegally-created single-family home to absorb it.
“Mahmood is not remotely a progressive,” wrote Tim Redmond of 48Hills in February, pointing to another of Mahmood’s votes with his moderate colleagues against a measure to protect small businesses from displacement. He called him instead a “classic neoliberal.”