It wasn’t yet one of the most contentious ballot measure fights in state history – pitting Democrats against Democrats, drawing national attention from political heavyweights, and netting hundreds of millions of Silicon Valley dollars to fight it.
asserted
It → pit → it
Trump had just signed the One Big Beautiful Bill Act, which dictated a trillion dollars of Medicaid, Affordable Care Act and other healthcare funding be cut over the next decade to offset sweeping tax cuts.
asserted
dollars → sign → cuts
When the bill goes into effect in January, that could mean more than 3.4m Californians will lose their coverage, including millions of children.
uncertain
Californians → go → children
“That’s why we were willing to do something that lots of people said was crazy,” said Dave Regan, the divisive architect of the billionaire tax and president of the healthcare union SEIU-United Healthcare Workers West (SEIU-UHW).
asserted
Regan → ’ → union
“To us, what’s crazy is doing nothing and watching millions of people lose coverage.”
asserted
millions → ’ → coverage
Now, with the midterms less than a week away, California voters will decide on whether to pass the ballot measure known as Proposition 40.
asserted
voters → decide → Proposition
The proposal would levy a one-time 5% tax on billionaires living in the state as of 1 January 2026, the proceeds of which would fund healthcare programs, along with some education and food assistance.
asserted
proceeds → levy → education
The initiative has its critics, even among Democrats, who point at its structure as a one-off tax that would only fund certain healthcare programs.
asserted
that → have → programs
The idea of taxing the Golden State’s ultra-wealthy has snowballed into a messy brawl over the last year.
asserted
idea → tax → year
Progressive politicians have become bedfellows with tech billionaires, opposition ballot measure campaigns have been mounted, Signal chats leaked, and boatloads of money have been spent.
asserted
boatloads → become → money
Tech billionaires have treated the proposal as an existential threat, dumping upwards of $356m into “independent expenditure-only” political action committees (Super Pacs) to stop it.
asserted
billionaires → treat → it
In the first two weeks of October, according to the most recent campaign filings, the opposition campaign spent more than $42.8m – surpassing $2.5m per day.
uncertain
campaign → accord → day
That money went to an army of consultants, who have been tasked with lobbying politicians, blanketing the airwaves with ads and placing op-eds in Latino newspapers across the state.
asserted
who → go → state
“This looks like it’s going to be the most expensive ballot measure ever,” said David McCuan, a political science professor at Sonoma State University.
asserted
McCuan → look → University
Meanwhile, the far-less-funded pro-Prop 40 camp has relied on viral social media campaigns from influencers and actors, including the artist Shepard Fairey and actor Mark Ruffalo, and raucous rallies headlined by leftwing politicians.
asserted
camp → fund → politicians
During one packed event in San Francisco earlier this month, Vermont’s Bernie Sanders said: “The whole country, and frankly people from around the world, are paying attention to what is happening here.”
asserted
what → say → attention
While Prop 40 is just one ballot measure election in one state, it is causing ripple effects nationwide.
asserted
it → cause → effects
It comes at a time when affordability is top of mind and the disparity of wealth in the US hasn’t been so stark since the Great Depression.
asserted
disparity → come → Depression
McCuan said the billionaires’ big spend was partially due to a fear of contagion to other states.
asserted
spend → say → states
Likewise, supporters say they hope the proposed tax is a harbinger for referendums on wealth inequality across the country.
asserted
tax → say → country
Regan and his union got started on their endeavor last summer.
asserted
Regan → start → endeavor
After Trump signed his bill on 4 July, Regan’s team began making calls.
asserted
team → sign → calls
They put together a working group of policy experts, economists, lawyers, researchers and political consultants, who came up with the one-time 5% tax to keep hospitals open and union healthcare workers in their jobs.
asserted
who → put → jobs
Regan is known for using the ballot measure process as a political tool to strongarm deals with lawmakers and push causes important to the SEIU-UHW.
asserted
Regan → know → UHW
Since 2012, the union has sponsored 48 initiatives.
asserted
union → sponsor → initiatives
The strategy with the billionaire tax was to sharpen the focus on inequality.
asserted
strategy → sharpen → inequality
“We worked to come up with something that could draw enough support from voters, and that could avoid a catastrophe,” Regan said.
uncertain
Regan → work → catastrophe
“We just bore down on that.”
asserted
We → bear → that
When their plan became public after the October 2025 filing deadline, the billionaires hatched a working group of their own.
asserted
billionaires → become → own
Chris Larsen, a cryptocurrency mogul, hosted a Christmas party in northern California’s swanky Marin county last December, according to Bloomberg.
uncertain
Larsen → host → Bloomberg
It was in a treehouse tucked into a grove of towering redwood trees.
asserted
It → tuck → trees
The singer Janelle Monáe performed and California governor Gavin Newsom was there, along with Google co-founder Sergey Brin.
asserted
Newsom → perform → Brin
Newsom’s relationship with Brin goes back decades to when he was mayor of San Francisco.
asserted
he → go → Francisco
The governor, now a presumed presidential candidate, had flown on Google’s jet with Brin, and the two men attended each other’s weddings.
asserted
men → presume → weddings
But a lengthy exchange they reportedly had at Larsen’s party was far from collegial.
uncertain
they → have → party
Brin confronted Newsom about the proposed billionaire tax, according to people who spoke with Newsom, Bloomberg reported.
uncertain
Bloomberg → confront → Newsom
The Google co-founder, currently worth about $245bn, told the governor it was forcing him to leave California.
asserted
it → tell → California
Newsom and Brin did not respond to the Guardian’s detailed list of questions.
asserted
Newsom → respond → questions
By that point, more than a dozen tech executives and prominent Silicon Valley venture capitalists had reportedly already joined an encrypted Signal group chat expressly dedicated to burying the billionaire tax, the San Francisco Standard reported.
uncertain
Standard → join → tax
Brin and Larsen were members, along with venture capitalist Marc Andreessen, PayPal co-founder Max Levchin, Stripe chief executive Patrick Collison and investor Ron Conway, according to people who saw the chats.
uncertain
who → accord → chats
…and 113 more, not listed.
The Aporia
