Dave Regan, president of SEIU-United Healthcare Workers West, has triggered a major political battle in California by pushing a ballot initiative that would impose a one-time 5% tax on the assets of the state's billionaires. The measure aims to generate roughly $100 billion to backfill anticipated federal cuts to Medicaid under the Trump administration, primarily directing funds to health care services with smaller allocations for education and food assistance.

Regan, 60, has led the 400,000-member union since 2009 and is known for aggressively using California's direct democracy system to advance labor goals. He has filed nearly 50 ballot measures since taking the helm, with eight reaching the ballot and successes including leverage for a $15 minimum wage in 2016 and a $25 hourly floor for health care workers in 2023. The billionaire tax, filed last year, responds to potential tens of billions in Medicaid reductions that Regan warns could lead to hospital and clinic closures and job losses. "We see this freight train coming at us," Regan said. "There’s no way to reroute the freight train."

The proposal has not yet qualified for the November ballot, needing about 875,000 valid signatures, but it has already upended state politics. In December, Governor Gavin Newsom met with Regan and urged him to withdraw it, joking, “Dave, what I would really like for Christmas is for you to withdraw the billionaire tax ballot initiative.” Regan replied that the governor lacked an alternative solution. Newsom has publicly criticized the effort by a "single labor leader," and his aides describe Regan as having alienated Democrats, Republicans, business, and even some labor allies.

Billionaires have reacted swiftly. Google co-founders Sergey Brin and Larry Page moved assets out of state in January, and Ripple co-founder Chris Larsen has committed $12 million to counter-initiatives and legislative races. Opponents argue the tax could harm California's economy, the world's fourth-largest, by driving away wealth and creating budget shortfalls, potentially undermining a separate school funding measure.

Labor is divided. While some groups like the Teamsters and AFSCME backed it, others preferred extending income taxes on high earners, and Regan's unilateral push bypassed a broader consensus. Supporters, including Senator Bernie Sanders, frame it as essential amid federal cuts, but critics within labor call Regan a "lone warrior" who breaks coalitions.

Regan's tactics echo past campaigns, such as spending $31 million to block dialysis regulations, which unionized 1,200 workers but spurred industry opposition. Through his Fairness Project, funded with $30 million from SEIU-UHW, he has passed dozens of measures nationwide. Despite controversies, including lawsuits alleging workplace issues, all settled or dismissed, Regan maintains the initiative has elevated national attention on wealth inequality and health care funding.