This article is from Power Play, a twice-weekly newsletter rounding up the latest City Hall and local politics gossip. To sign up, visit The Standard’s newsletter page.

We all knew former Supervisor Aaron Peskin would be name-checked at some point this election.

This time, it’s by one of his political archenemies: GrowSF. 

The Mayor Daniel Lurie-aligned group, the big kahuna in moderate political moneymaking these days, is running ads against D2 candidate Lori Brooke, Power Play has learned.

Their line of attack? She’s a Peskin in sheep’s clothing. 

Brooke is running against Supervisor Stephen Sherrill, a close ally of Lurie’s and a GrowSF favorite who was appointed by former Mayor London Breed in 2024. Brooke and Sherrill will face off in a June contest to fill the remainder of Assemblymember Catherine Stefani’s term before a November election for a full, four-year term. 

Brooke and Sherrill are not all that different on topics like public safety or homelessness, but when it comes to housing, hoo boy. Brooke’s detractors like to paint her as the NIMBY Queen of San Francisco. She’s been a fierce critic of Lurie’s state-mandated “Family Zoning Plan,” which aims to increase housing production across the city. Sherrill has been a defender of the proposal, walking a tight line between his wealthy D2 constituents who don’t want their views blocked and the city’s rising and powerful YIMBY faction.

Power Play is told the GrowSF ads will cast Brooke as a neo-Peskin, playing off his reputation for blocking housing. It will tie Brooke’s current donors to Peskin-world, including names like land use attorney Richard Drury and progressive communications consultant Dale Carlson, both of whom gave to the former supervisor’s 2024 mayoral campaign. Brooke has also hired staffers for her campaign, Forrest Cameron and Jamie Hughes, who have worked for Peskin’s mayoral bid.

“It’s the same agenda, the same team, the same donors, and the same philosophy — and that means the same results: a deeply unaffordable San Francisco stuck in bureaucratic gridlock,” said Steven Bacio, co-founder of GrowSF, in a statement.

It’s hard to say how effective the ads will be. Peskin hasn’t been in office for more than a year, and some voters’ resentments toward him may have dampened. 

But GrowSF also has a huge war chest and can pepper voters with a consistent stream of ads. The latest fundraising figures show the group has scooped up $267,000 for its pro-Sherrill PAC. Sherrill’s June campaign has hoovered up $246,209, while Brooke reports $159,273. And the strategy has been tried before: Former Supervisor Mark Farrell accused his then-opponent Janet Reilly in a 2010 D2 race of being tied to Peskin. Reilly, the favorite, lost to Farrell by a close margin.

• Power Play: Five key questions for November’s general election

Meanwhile, Brooke and Peskin had some choice words for GrowSF.

“District 2 voters are smart enough to know this is foolish and desperate,” Brooke said in a statement. “You know Stephen is scared when they have over a million dollars and still have to use the Aaron Peskin boogeyman.”

Peskin invoked Sherrill’s father, a longtime Republican donor with ties to the firearm manufacturer Remington Arms: “It sounds like a petrified Stephen Sherrill got his right-wing, gunmaker father to fund GrowSF’s absurd hit piece.” — Gabe Greschler

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OUTSIDE MONEY: Two outside spending groups are entering the San Francisco congressional race to boost their preferred candidates to replace retiring Speaker Emerita Nancy Pelosi.

Working Families for San Francisco, which supports Supervisor Connie Chan, has received $200,000 (opens in new tab) from the hospitality workers union UNITE HERE, affiliated with Local 2 in San Francisco. It has long been rumored that labor groups would launch an independent expenditure committee to support Chan, who has backing from progressive unions, but has been trailing her main rivals, state Sen. Scott Wiener and Saikat Chakrabarti, in fundraising. More money is expected to flow into the effort, according to David Ho, a political consultant running the IE effort.

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The group has already spent $100,000 on phone banking, canvassing, and digital media production, meaning ads could start appearing soon.

A separate IE, Jobs and Democracy, backed by AI company Anthropic, plans to spend $500,000 (opens in new tab) to support Wiener, according to Politico. The senator has been pushing legislation at the state level to regulate the AI industry.

Both campaigns declined to comment, as candidates are prohibited from coordinating with outside spending groups.

But all of this IE spending is unlikely to match what Chakrabarti has been pouring into the race — $5 million of his own money. The first major IE in the contest, Abundant Future, is supporting Wiener and has raised about $550,000 so far to attack the former tech worker and Rep. Alexandria Ocasio-Cortez aide. — Han Li

SORRY, SAIKAT: Speaking of Ocasio-Cortez, her cold shoulder to Chakrabarti just went from chilly to arctic tundra. 

On Friday, AOC endorsed Philadelphia congressional candidate Chris Rabb, a progressive (opens in new tab) who has pushed for state-level reparations for Black Americans. But didn’t AOC just tell reporters she’s gotta be picky about endorsements, her excuse for withholding an endorsement of her former chief of staff, Chakrabarti?

Let’s run back the clock to mid-April, when a reporter asked AOC if she’d back Chakrabarti. She hemmed and hawed, saying she has a lean team and wants to think about “how much of myself I’m pouring into this, and how much of myself I want to pour into the task at hand.” 

Progressive media pundits at “The Young Turks (opens in new tab)” and “Breaking Points (opens in new tab)” laid into AOC. “What was that? That was a Kamala Harris-like word salad,” said Cenk Uygur, host of “The Young Turks.” 

One week later, Ocasio-Cortez endorsed Rabb. Tough look for Chakrabarti. — Joe Fitzgerald Rodriguez

THE D4 DONOR DANCE: The newest campaign filings for the District 4 supervisor candidates show incumbent Supervisor Alan Wong is neck and neck in fundraising with his progressive challenger, legislative aide Natalie Gee, at roughly $120,000 raised each (not counting outside money, which is also roughly equal). 

But beyond the numbers, the current and former City Hall insiders who are funding them reveals something about the candidates themselves — especially since both had careers under City Hall’s gilded dome.

By Power Play’s tally, Gee is getting more insider support, with just over 30 past and present city officials and government workers backing her to the tune of about $6,800. That list includes former Mayor Art Agnos; Supervisors Connie Chan, Myrna Melgar, Jackie Fielder, and Shamann Walton; Superior Court Judge Michael Begert; and a boatload of fellow legislative aides. Chakrabarti, the congressional candidate, also donated to Gee.

Only a dozen officials back Wong, to the tune of $2,250. His City Hall backers mostly stem from the mayor’s office — not a surprise, considering he’s a Lurie appointee. They include mayor’s office Chief of Staff Staci Slaughter, Deputy Chief of Staff Aly Bonde, liaison to the Board of Supervisors Adam Thongsavat, and Director of External Affairs Han Zou. Oh, and of course, Lurie himself.

Some of the challengers who have raised less funds nonetheless have some interesting local players among their donors. Sitting with a respectable $111,000 raised, hardware store owner Albert Chow netted donations from former school board member Ann Hsu and former SF Democratic Party board chair Mary Jung. And educator David Lee, who raised $98,000, netted donations from the strangest bedfellows you could imagine in SF politics: progressive firebrand and recalled District Attorney Chesa Boudin and Republican socialite (opens in new tab) and philanthropist DeDe Wilsey. — J.F.R.