The AI tech boom, soaring rents, and Donald Trump’s return to office may have created the perfect political moment for San Francisco progressives to stage a comeback.

At the center of that fight is the hottest ballot measure this June: Proposition D, the so-called “Overpaid CEO Tax” that would increase taxes on large corporations with wide pay gaps between executives and workers. The measure has become the latest signal of a growing anti-big tech and anti-billionaire political narrative emerging in San Francisco and beyond.

“The results on Election Day are going to be really indicative of whether this ‘eat the rich’ movement is resonating with the electorate,” Jay Cheng, a political consultant working on the campaign to defeat Prop. D, told The Standard.

Cheng said the push is not limited to San Francisco, pointing to similar tax-the-rich proposals in Washington state (opens in new tab) and New York City (opens in new tab), as well as a closely watched billionaire tax ballot measure headed for California voters this November.

“There’s an overall effort from labor and unions to make ‘eat the rich’ a defining political issue,” he said.

Keally McBride, a politics professor at the University of San Francisco, said there is a growing sense among voters that “enough is enough” when it comes to wealth concentration and widening inequality.

Unlike everyday local political issues such as road paving or child care, McBride said taxes on the wealthy function more as a barometer of broader political sentiment.

“I think the United States is kind of hitting this boiling point,” McBride said. “People are no longer trusting that the free market will operate the way it has served them.”

The city’s overpaid CEO tax is not entirely new. Voters approved a similar executive pay tax in 2020, but it was effectively rolled back in 2024. Labor groups are now attempting to revive it.

David Harrison, director of public policy at the Chamber of Commerce, argued that the tax represents a step backward. While it may feel emotionally satisfying to some voters, he said, it would do little to address the city’s underlying challenges.

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“The AI boom and renewed investment in San Francisco are signs that the city is beginning to recover,” Harrison said. “But recovery is not the same as stability.”

Cheng said the No on D campaign (opens in new tab) is framing the measure around San Francisco’s economic recovery. “We’re in the middle of a recovery right now, but we’re not fully recovered,” Cheng said. “There’s concern this could derail that recovery.”

Supporters of Prop. D, largely backed by organized labor, have raised roughly $3.3 million. Major donors include congressional candidate Saikat Chakrabarti, various branches of the Service Employees International Union, and several nurses’ and public-sector unions.

“Don’t get it twisted. Prop D is about one thing — requiring billion-dollar corporations to pay their fair share like everyone else,” Scott Mann, the Yes on D campaign spokesperson, said in a statement. “This measure is truly about protecting care, not corporate greed.”

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Opponents, led by the Chamber of Commerce and backed by corporate and billionaire donors, have raised about $6.5 million. The Standard’s chairman, Michael Moritz, donated $625,000 to help defeat Prop. D.

The chamber also placed Proposition C, a competing measure that would reduce business taxes, on the ballot. Because the two measures conflict, if both pass, only the one receiving more votes would take effect.

The issue has divided San Francisco’s political establishment. Mayor Daniel Lurie and the San Francisco Democratic Party oppose Prop. D, while a supermajority (opens in new tab) of SF supervisors and Speaker Emerita Nancy Pelosi support it.

A city report estimated that the measure would generate more than $200 million in annual revenue if approved, but also warned that it could prompt some major corporations to leave San Francisco, resulting in the loss of roughly 900 jobs (opens in new tab).

In recent years, moderates have largely dominated San Francisco politics, and Prop. D has emerged as the progressives’ biggest political push this election cycle. Cheng, a longtime moderate political operative, said moderates have made major progress but now fear a political backlash.

“There is a fear of a pendulum swing back,” Cheng said. “[Progressives] are trying to find a narrative that swings that pendulum back faster.”

Former Supervisor Aaron Peskin, a progressive backing Prop. D, argued San Francisco voters historically support economic stimulus during downturns but become more open to taxation during boom periods.

“When the economy is overheated, the electorate is more inclined to tax it and get its fair share,” he said.

Peskin said the city supported rolling back the CEO tax in 2024 because officials wanted to recruit and retain businesses during a fragile economic period. But now “rents have gone through the roof, evictions have gone up, the cost of living has gone up, AI has launched into the stratosphere,” and voters are more inclined to believe wealthy corporations should pay their fair share.

Peskin argued that Trump’s policies could further shift San Francisco voters leftward. He said wealthy CEOs have benefited from federal tax breaks under Trump while cities like San Francisco face cuts from the federal government, strengthening the case for higher taxes on corporations and top executives.

Four months ago, the Prop. D campaign released a poll showing 60% support for the measure. No other public polling has been released since, but insiders believe the race has tightened as both sides ramp up spending in the final weeks of the campaign.

McBride said the San Francisco measure could become a bellwether for the statewide tax fight in November. She questioned whether campaign spending alone would determine the outcome, arguing that broader economic frustrations and voter sentiment may ultimately matter more.

“At a certain level, all those flyers arriving in your mailbox start canceling each other out,” she said. “What becomes decisive is people saying, ‘I’m angry about how much money these people make, and this is my opportunity to register that discontent.’”