Billionaire’s $66M Gamble Backfires Spectacularly

Billionaire leftist Tom Steyer just dumped another $28 million of his hedge fund fortune into California’s governor race, hitting $66 million self-funded—buying his way past experienced rivals in a state already crushed by progressive failures.

Story Snapshot

Steyer’s $66 million self-funding makes up 99.8% of his large donations, dwarfing rivals’ war chests in the race to replace Gavin Newsom.
Despite massive spending on TV ads, recent PPIC polls show Steyer in a dead heat with Katie Porter and Eric Swalwell, tied in a five-way primary.
History warns of failure: Self-funded billionaires like Meg Whitman ($144M) and Al Checchi ($40M) crashed in past California races.
Steyer pushes affordability fixes for housing and schools, but voters remain skeptical of unelected “rich guy” outsiders promising progressive reforms.

Steyer’s Massive Self-Funding Surge

On February 25, 2026, Tom Steyer disclosed a $28 million personal donation to his California gubernatorial campaign, pushing his total self-funding to $66 million. This amount represents 99.8% of large donations received. Steyer, a 68-year-old former hedge fund manager, entered the race late 2025 to succeed term-limited Gov. Gavin Newsom. His strategy relies on wealth to compete against better-known politicians like Reps. Katie Porter and Eric Swalwell. In 2025 alone, he spent $27 million on TV ads for his bid and $12 million backing Newsom’s Proposition 50, which aimed to gerrymander congressional districts. This flood of cash gives Steyer advertising dominance, but echoes past self-funded flops that burdened California taxpayers with little return.

Rivals and the Crowded Primary Field

The June 2026 Democratic primary pits Steyer against Porter, Swalwell, and others in a virtual five-way tie per PPIC’s February survey. Affordability dominates voter concerns amid California’s sky-high housing costs, utility bills, and lagging schools. Porter leverages economic populism, while Swalwell holds endorsements like Sen. Adam Schiff’s. Steyer claims independence, stating he owes nobody, and highlights 14 years of progressive activism on climate and taxes. Yet experts like Democratic strategist Garry South warn voters reject untested billionaires. Steyer’s TV blitz and hires from winning New York progressive campaigns aim to build grassroots support, but middle-of-pack polling persists despite the spending.

Steyer’s Record and Policy Pitches

Steyer exited finance in 2012 for left-wing causes, signing the Giving Pledge and leading ballot wins against Big Oil, for tobacco taxes, and closing corporate loopholes—raising billions for healthcare and schools without new taxes. His 2020 presidential run cost $340 million but flamed out early. Now, he targets California’s unaffordability, criticizing high-speed rail waste and vaguely endorsing single-payer healthcare. Supporters like Ro Khanna, California Nurses Association, and school employees back his anti-corporate reformer image. Critics note policy flip-flops and a wealth disconnect from struggling families, positioning him as another elite meddling in state affairs already strained by Newsom-era mismanagement.

Power dynamics favor Steyer’s ad war chest, but Newsom’s legacy looms large. An independent committee dropped $4.8 million on San Jose Mayor Matt Mahan, signaling fractured support. LA Times columnist Skelton doubts Steyer’s “billionaire vs. billionaires” messaging sways working Californians facing real pain from progressive overreach.

Billionaire lefty Tom Steyer drops staggering $66 million into California governor's race https://t.co/iQlARksivi pic.twitter.com/0CyXi70ZAj

— New York Post (@nypost) February 27, 2026

Historical Precedents and Voter Skepticism

Past self-funders failed spectacularly in California. Republican Meg Whitman poured $144 million into the 2010 governor race and lost. Democrat Al Checchi spent $40 million in the 1994 primary to no avail. Steyer differentiates via activism but faces similar “rich outsider” backlash. Short-term, his spending tightens the race, forcing rivals to scramble for funds. Long-term, success could validate billionaire buy-ins; failure reinforces rejection of unelected elites. Working families, renters, and homeowners stand to gain or lose from his affordability promises, while his climate and equity pushes amplify left-wing agendas in a state conservatives see as a cautionary tale of fiscal irresponsibility.

Expert views split: Supporters praise his Giving Pledge commitment; neutrals say money buys visibility, not votes in this ho-hum field. With President Trump securing borders and slashing waste nationally, Californians may eye Steyer’s bid warily as more big-money progressivism.