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.

Hours after The Standard’s investigation into Mayor Daniel Lurie’s permit overhaul was published, Supervisor Connie Chan had sharp questions for department heads at a Wednesday-afternoon Budget and Appropriations Committee meeting. 

Former employees of OpenGov, the company hired for Lurie’s permitting modernization effort, told The Standard they knew the firm would miss deadlines, and current city staffers said the software lacks important features. Lurie awarded OpenGov in a no-bid contract, claiming it was the only company that could meet its deadlines. 

But deadlines have been blown through.

SF Planning’s director, Sarah Dennis Phillips, and the interim Department of Building Inspection director, David Kane, were in the hot seat as Chan had pointed questions about the permit overhaul in light of The Standard’s reporting. The exchanges became tense at times.

The city is seeking to renew the OpenGov contract for six years, at a price of $6.5 million — a decision that must go before the Civil Service Commission before heading to the supervisors for approval.

Chan’s suspicions are part of a bubbling skepticism against Lurie’s permit efforts. The Civil Service commissioners have already delayed a hearing to approve OpenGov’s contract renewal after claiming that the city did not provide them with enough information about opposition to the project from a public-sector union. Some commissioners expressed serious concern about the contract during a May 4 meeting before pushing the vote to this Monday. 

Phillips defended the adoption of the software, stating that the department is “very happy with the results” and that the “system is performing.” She conceded that there had been bumps in the road on timelines: “We are erring on the side of doing permits correctly, rather than in volume. That does take more time, and it means things are moving more slowly than we think.”  The current contract was set to deliver 15 permit types by March onto a new OpenGov-powered platform. Today, fewer than half are available.

Chan remains wary of the project’s trajectory. She asked the departments to provide evidence that OpenGov is making permitting more efficient and to outline a Plan B if OpenGov is shelved — a nightmare scenario for Lurie. She quoted The Standard’s reporting in which a city employee said San Francisco is essentially subsidizing OpenGov’s product advancements.

“I’m not inclined to fund the research and development of OpenGov,” Chan said. “What I’m inclined to fund is the development of a permanent permitting system that actually works for San Franciscans.”

— Gabriel Greschler

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THE BIG SAIKAT SPEND: The centimillionaire congressional candidate Saikat Chakrabarti has pledged to spend whatever it takes to win. Now he’s helping local propositions too. On Tuesday, Chakrabarti dropped a cool $100,000 (opens in new tab) into the campaign for Proposition D, the Overpaid CEO Tax. If approved on the June’s ballot, it would raise taxes for any company with a wide pay gap between the CEO and the median salary of workers worldwide. 

The measure is backed by a bevy of unions (opens in new tab) that hope the funds will plug San Francisco’s budget hole: SEIU Local 2015, SEIU Local 1021, IFPTE Local 21, AFSCME 3299, and Teamsters Joint Council 7. That begs the question: Will Chakrabarti’s contribution help him finally make inroads with labor?

“Labor bases its support on the shared values candidates have with working families,” a spokesperson for the Prop. D campaign stated succinctly.

Chakrabarti is certainly making his case.

“These companies just received massive federal tax breaks under Trump, so asking the largest corporations, that are paying CEOs more than 100 times their median employee’s salary, to contribute a little more isn’t going to hurt them,” Chakrabarti said. “But cutting homelessness services, emergency response programs, and public safety resources would hurt thousands of San Franciscans.”

For her part, Chan has so many unions supporting her (opens in new tab) congressional run she could practically start her own labor council. Though Chakrabarti shares labor’s values, unions are loath to endorse wealthy candidates for any office. But if the alternative is state Sen. Scott Wiener, who pissed off SEIU California enough that they un-endorsed (opens in new tab) him, it’ll be interesting to see if progressive labor collectively holds its nose to back either of them in June. 

— Joe Fitzgerald Rodriguez

YOU’RE WELCOME, L.A.: San Franciscans are generally proud to beat L.A. with our superior burritos, walkability, and fog over smog. However, we’ll have to begrudgingly concede that we’re on par in one respect: Both are now the scene of the political shenanigans of Jay Cheng, the consultant who earned Lurie’s ire and recently parted ways with Neighbors for a Better San Francisco under mysterious circumstances. Power Play readers will recall the rumor of an ethics investigation into Neighbors that may have ensnared Cheng. 

Cheng makes a cameo in an L.A. Times article last weekend (opens in new tab) detailing a dark money campaign to attack Los Angeles City Councilmember Eunisses Hernandez, a Democratic Socialist. Dark money refers to political spending wherein entities fund other entities, which fund other entities, to disguise the true source of attack ads. The piece highlights Cheng’s role as a consultant for a nonprofit working to elect “centrist” and “moderate” candidates to office in the City of Angels. 

It’s one of the first clients of his new shop, Jay Cheng Strategy. When reached by text, Cheng said he now has clients in multiple cities to “help them move in a moderate direction, like we did in SF.” He declined to name those cities but said he will do so in the coming weeks.

When asked about the accusations in the article, Cheng replied, tongue in cheek, “Wherever there is dark money, there is Jay Cheng!” 

You don’t say!

— J. F. R.

THAT WAS FAST: Conor Johnston and Eric Kingsbury, who were staffers to Mayor London Breed, came forward (opens in new tab) Monday to accuse their former boss of appointing Supervisor Stephen Sherrill to his position in the hopes that she’d get a job from Michael Bloomberg. Sherrill issued a statement asserting that the vetting process for the supervisor seat was rigorous, and that she’s proud of Sherrill’s record but, curiously, doesn’t outright deny the chief allegation of a quid pro quo. Either way, we’ll be darned if Sherrill’s chief opponent in the June election, community activist Lori Brooke, didn’t move quick to capitalize on the accusations. 

Her campaign snapped up www.stephensherrill.com (opens in new tab), which redirects to The Standard’s article. Cheeky! And it whipped up attack mailers using the most salacious quotes from Mission Local (opens in new tab) and The Standard, which will flutter into District 2 voters’ mailboxes this week. 

“District 2 deserves better than a supervisor who has made their career in backroom political deals,” Brooke told Power Play. 

We doubt that’s the only hit coming. Considering the avalanche of money from four independent expenditure committees supporting Sherrill, Brooke will need every swing.

— J. F. R.

TABLOID TIME: San Francisco’s media ecosystem is apparently booming (opens in new tab), and we sure welcome some competition — for better or worse.

The infamous San Francisco Inquirer, which the Chronicle (opens in new tab), Standard, and San José Spotlight (opens in new tab) debunked three years ago as a political operation backing a Bay Area-based tribe (opens in new tab), is active again, publishing sensational headlines about the race to succeed Rep. Nancy Pelosi.

Recent stories on the site, with no authors listed, are critical of Wiener and Chan, while offering more favorable treatment (opens in new tab) to Chakrabarti.

“Pelosi declines to endorse Wiener, widely seen as a stunning rebuke,” one headline says (opens in new tab). Well, stunning to who? We all know who the speaker emerita’s preferred candidate is.

The site’s founder, Matt Ricchiazzi, an East Coast-based consultant accused of running fake news websites (opens in new tab), denied any involvement with the campaigns.

“I don’t have any client interests in the race. I’m just sharing my opinion about the contenders,” Ricchiazzi told Power Play.

Chan’s campaign blasted a story on the site (opens in new tab) linking the Chinese American immigrant to the Chinese government’s influence. “These are dirty and racist tactics. Whoever is paying for this is a coward and is furthering anti-Asian hate for personal and political gain. It’s despicable,” said Julie Edwards, Chan’s spokesperson. 

Federal campaign filings do not show payments to Ricchiazzi connected to the race, but Chakrabarti may have a friendly relationship with the tribe that paid Ricchiazzi, according to a 2025 social media post (opens in new tab). His campaign denied any relationship with Ricchiazzi.

If there’s one good thing to say about the website, it’s packed with ads promoting local businesses — including our favorite Hook Fish Co. and City Lights Bookstore.

— Han Li

KUMBAYA: Four years ago, Supervisor Shamann Walton was scrutinized for dressing down a sheriff’s cadet who was serving as City Hall security. Walton called the cadet the N-word and later accused staffers of the Sheriff’s Department of targeting him for his scrutiny of the office. Recriminations followed, alongside hurt feelings and a lot of fear. Breed called on Walton to apologize.

My, how things have changed.

At the Board of Supervisors’ regular meeting Tuesday, Walton led a round of praise for the sheriff’s cadets, who, importantly, are not sheriffs in training; it’s just a classification of an unarmed segment of the sheriff’s staff. It was a wonder to see. Led by Walton, nearly every supervisor heaped kind words upon the cadets — who stood by a podium at the Board of Supervisors chambers, beaming — for their demeanor and professionalism.

So, what gives? Are we all friends now? That’s right, Sheriff Paul Miyamoto told us outside the chambers. The relationship has “had its ups and downs,” Miyamoto admitted, but Walton “actually reached out and wanted to recognize the cadets for the work they do. I think it was intentional to make sure they feel appreciated.”

“Everything else,” the sheriff said, “is water under the bridge.”

— J. F. R.