Left activists who love Sen. Bernie Sanders have this year flocked to a surprising new champion: hedge fund billionaire Tom Steyer.

In his campaign for California governor, Steyer has racked up the endorsements of Our Revolution (a group founded by Sanders 2016 campaign notables) and the California Nurses Association (the state’s leading champions of single-payer healthcare).

And earlier this month, even the Democratic Socialists of America’s California chapter praised Steyer as “most progressive of the current viable candidates for governor” — and advised against making a further-left protest vote.

Though all tout Steyer’s positions on the issues, the optics of the anti-billionaire left backing a candidate who has spent $132 million of his own money to saturate the state’s airwaves with his ads may seem strange.

Yet Steyer isn’t the only example of a very wealthy pol who’s won at least some left enthusiasm:

Wealthy politicians who can plow millions into their political runs are hardly new, of course, with plenty of current examples in each party, as well as independents like the late Ross Perot. Today’s progressives frequently trace their roots to Franklin D. Roosevelt, who was himself a scion of one of the most well-connected families of its era.

But the rise of this specific class of left-leaning ultra-wealthy candidates is noteworthy, because it comes after years of Democratic alarm over the influence of megadonors on elections in the Citizens United era — and over how billionaires have increasingly imposed their will on the government and society more broadly. (Hence the “Fighting Oligarchy” rallies from Sanders and US Rep. Alexandria Ocasio-Cortez around the country last year.)

In conversations about this broader topic with left activists, I heard some mixed feelings about backing wealthy candidates, especially prolific self-funders like Steyer — but also a general sentiment that, if they’re saying the right things on the issues and making the right enemies, they could be worth supporting.

“Every billionaire is a policy failure,” said Joseph Geevarghese, executive director of Our Revolution. “That being said, we have to operate in the world that we’re in. And in this world we happen to have a billionaire candidate who is ideologically aligned with our organization and our policy priorities.”

Others on the left have gone even further, and questioned whether the left’s anti-billionaire rhetoric itself has been flawed.

“The fact that the DSA and many progressives in California are coalescing around Steyer underscores the problem with casting billionaires, per se, as the enemy,” Katrina vanden Heuvel, editorial director and publisher of The Nation, wrote on X. “This frame doesn’t fare well in the real world, where some billionaires are very much part of the problem, while others are part of the solution.”

The candidates in question don’t hide from their wealth, nor do the progressives and socialists backing them pretend these tensions aren’t there. But each one has found their own individual way to address concerns — and an audience willing to hear them out. Here’s what the modern playbook looks like for a progressive tycoon seeking elected office.

A hedge fund billionaire who started his career at Goldman Sachs, Steyer isn’t exactly new to left causes — he’s been a major funder of climate change activism going back to the Obama-era fight to block the Keystone XL pipeline. Then, during Donald Trump’s first term, he spent millions on a push to get the president impeached, and then more than a quarter-billion dollars on his own quixotic presidential bid (his best showing was 11 percent in South Carolina).

But the open-seat California governor’s race provided a new opportunity. Steyer’s outreach to the left began with his choice of campaign consultants, as he signed on Fight Agency, the buzzy firm launched in January 2025 that’s behind left insurgent candidates such as Graham Platner in Maine and New York City Mayor Zohran Mamdani.

Any consulting firm would typically love to land a big-spending self-funder, but Steyer was off-brand for Fight. Initially, its co-founder Rebecca Katz said she told Steyer’s team all the reasons she’d never work for a billionaire — but they said Steyer still wanted to meet with her, and she agreed. After talking to her for an hour, he won her over.

“I said, ‘My first question for you is: Should billionaires exist?’ He said: ‘Yes, but we should tax the hell out of them,’” Katz told me. “He wanted to change the way things are done and wanted to disrupt the system. He talked a lot about costs, the systems that were rigged from the inside, and the urgency of the moment. Being a billionaire, he’s not the messenger I would’ve expected, but there was no one else saying what he was saying.”

Steyer then set about wooing other left groups, and two of his positions mattered most of all.

One was a controversial wealth tax proposal going up for a statewide vote this year, a onetime tax of 5 percent of the wealth of residents with over $1 billion in assets. Gov. Gavin Newsom strongly opposes the proposal due to fears it would drive investment out of California. Most Democrats in the race have declined to support it, worrying it is badly designed despite sympathy for its aims. But even though Steyer has expressed some reservations about the wealth tax proposal, he’s also said he’d vote for it — and posed for pictures wearing a hat with the label “class traitor.”

“I understand it’s not the perfect measure, and that Steyer has said that,” Geevarghese, Our Revolution’s executive director, said. “But he’s willing to endorse it, he’s willing to support it, he agrees with the principle that extreme wealth should be significantly taxed.”

The second key issue is Steyer’s support for single-payer healthcare in California, which was crucial in winning him the nurses union endorsement. This is a promise that has frequently been made by California politicians, including Newsom — but it keeps not getting done. Leftists blame this failure on the Democratic establishment being captive to the insurance industry. Of course, there are other obstacles as well — politicians may fear disrupting voters’ current care, and no one seems to know how the cash-strapped state will pay for it (or get the Trump administration’s permission, which they’d need).

Steyer hasn’t put forth a serious proposal on paying for it — “God is going to be in the details,” he recently told KFF Health News — but he has promised to get single-payer done more consistently and unambiguously than his rivals in the race.

Both the wealth tax proposal and statewide single-payer tend to get the sideeye from wonks, who suspect they’re pandering promises that will work out very poorly in practice. But many on the left view such commitments as a promising sign that Steyer will break with the party’s establishment and the conventional wisdom about how things are typically done.

And, indeed, the evident reluctance of state party bigwigs to back Steyer — many initially were leaning toward Eric Swalwell, who dropped out over sexual misconduct allegations, and now seem to have switched to back former Health Secretary Xavier Becerra — is a draw in and of itself, as is the financial independence that lets Steyer avoid fundraising from moneyed interests.

This is central to Steyer’s pitch. “I’m the only person running for governor who’s taking them on,” he told my colleague Zack Beauchamp in a recent interview. “I’m the only person they’re worried about. I’m the only person they’re spending a nickel against and they’re spending tens of millions of dollars to stop because they think they run the state.”

It is quite possible that all Steyer’s millions in spending and his left activist support will be for naught. Recent polls have mostly shown Steyer behind Becerra and one or two Republican candidates (California’s primary advances the top two finishers, regardless of party, to the general election). But the race remains close, and perhaps, if a billionaire spends enough money and wins enough hearts, he’ll be able to achieve his dream.

Four years before Steyer’s governor bid, it was another billionaire winning strange new respect from the left: Illinois Gov. JB Pritzker.

Pritzker was surely not the left’s candidate when he first ran for governor in 2018; progressive support in the Democratic primary went to second-place finisher Daniel Biss, who ran on a “middle-class governor” platform that called out his opponent’s wealth.

But in his first term, Pritzker passed a series of progressive bills — a minimum wage hike, marijuana legalization, and pro-choice and pro-union laws, among many others — that summed to an impressive record of achievement. “Pritzker has been signing bill after bill, and many of them are exactly what progressives want,” Nathan J. Robinson, a prominent socialist commentator, wrote in Current Affairs in 2022.

So during a period of frustration with President Joe Biden’s struggles to pass his agenda, Pritzker started to look pretty good to some. Online, a memeified version of Pritzker as a badass progressive hero was embraced — with some amount of irony — by accounts such as “Socialists for Pritzker.”

Writing in Jacobin magazine, Ben Burgis pointed out that this was all a bit strange because Pritzker was a “thoroughly mainstream Democrat” — but argued that he contrasted with the party’s national leaders because he “actually followed through.” (Though perhaps the difference is more that Pritzker, unlike Biden, had supermajorities in both chambers of the state legislature.)

The physicality and personal charisma of Pritzker — who is overweight and happy to call attention to that by, for instance, making “Think Big” his campaign slogan — was also part of the appeal for some. “JB Pritzker is a unicorn for the Democratic Party in 3 ways: he is enormous, doesn’t come off as particularly intellectual, and has good instincts. you really never get all 3 in a Dem,” Felix Biederman, co-host of the Chapo Trap House podcast, tweeted in 2022.

But the interest is also mutual. Pritzker has said he takes pride in winning over Sanders supporters in his state— and he’s well aware he’ll have to find ways to address their skepticism in the future. In an interview with The Atlantic, he called his personal fortune an “obstacle” to overcome should he run for president 2028.

The enthusiasm for Pritzker may have been situational; it’s not clear it would carry over to a potential 2028 campaign, where the left could have other champions. Ocasio-Cortez is the first name on everyone’s lips there, but there’s also been chatter around another longtime Sanders backer — Rep. Ro Khanna.

Khanna busted into Congress by challenging an aging Democrat, Mike Honda — unsuccessfully in 2014, and successfully in 2016 — for a Silicon Valley House seat. But he earned his anti-establishment cred early by endorsing Sanders over Hillary Clinton, and then by co-chairing Sanders’s presidential campaign in 2020.

Khanna is also, it turns out, quite rich — through his wife, whose immigrant father started an auto transmission business in Ohio. However, Khanna has publicly stressed that the wealth that shows up on his financial disclosure forms is “my wife’s money from prior to marriage over which I literally have no say or claim,” and that it is largely held in an independent trust. (Khanna also differs from the other politicians mentioned in this article in that he does not self-fund his campaigns.)

Initially, Khanna didn’t shy away from his connection to his wealthy district’s elites. And for a time, he seemed to be pulling off the delicate balancing act of cultivating support from both Bernieworld and the tech industry, including a longtime relationship with Musk, by emphasizing a more pro-growth and futurist approach to progressivism.

But the California wealth tax initiative this cycle finally forced him to pick a side — and he backed the tax, stoking fury among wealthy tech donors and earning him a Democratic challenger, Ethan Agarwal.

In office, Khanna has shown a knack for putting himself at the forefront of major national topics, such as by co-authoring the bill to release the Epstein files. Khanna is weighing a 2028 presidential run, and according to NBC News’s Natasha Korecki, he has lined up support from some key Sanders campaign figures and may run even if AOC runs too.

Not far away from Khanna’s district, another quite wealthy candidate is hoping support from the left can carry him into Congress. Saikat Chakrabarti, a software engineer whose early work at the payment startup Stripe helped make him a centimillionaire, is running for Pelosi’s open House seat in San Francisco.

“I experienced that lottery economy, that the startup economy really is,” Chakrabati said on a podcast last year. “It’s this system where you can just hit it big if you just happen to be in the right place at the right time.”

Like Khanna, Chakrabarti has longtime ties to Bernieworld — he worked on Sanders’s 2016 campaign, and in 2017 co-founded Justice Democrats to back further left candidates in Democratic primaries. Four of the candidates he backed, once elected, would become the initial members of “The Squad” — including AOC, who Chakrabarti worked for as chief of staff. (He left after a few months, reportedly because his public criticism of moderate Democrats caused controversy.)

Now, Chakrabarti is campaigning with streamer and leftist influencer Hasan Piker, heaping criticism on the Democratic establishment, promising a “political revolution,” and saying he’ll spend whatever it takes to win. Recent polls have shown him behind the frontrunner, state Sen. Scott Wiener, but if he wins second place in next month’s primary he and Wiener will face off in November’s general election.

Each of the above politicians are different in their own way, with different paths to relevance on the left. Steyer’s a longtime donor to progressive causes, Pritzker’s a larger-than-life personality who emphasizes his competence, Khanna’s a policy wonk with a knack for media, and Chakrabarti was an early organizer for “The Squad” before it existed. There’s no one quality that unites them — except that each has an enormous net worth.

But one thing that struck me in talking to their supporters was how some of their arguments for the virtues of a candidate like Steyer — that his wealth in this case helps make him independent of the establishment and big donors, and more willing to take on the system — resemble those arguments made for a certain other billionaire: Donald Trump.

Nobody would mistake Trump for a Sanders-style critic of money in politics. But in his 2016 primary campaign, the only one that he (mostly) self-financed, he and his supporters frequently argued his money gave him the unique ability to take on both the party establishment and special interest groups. Trump himself argued his opponents were all bought off by the top party donors (many of whom he later embraced) and that his wealth gave him a unique perspective on how elites held down the working class.

There’s a perverse logic that in our current legal environment, where individual donors and industries are allowed to spend hundreds of millions of dollars to influence races, turning a megadonor into a candidate makes a certain kind of sense. If he can spend his own money, at least he’s not pandering to get money from everyone else!

Yet progressives don’t want a billionaire in office who’s truly empowered and independent from special interests — they want one very dependent on the right kind of special interest groups, that is to say, on themselves.

“You do have to think about who that candidate will be beholden to if they enter office,” American Prospect editor David Dayen said on a recent podcast. “Certainly if Steyer wins, he would have to thank the teachers union, progressive groups, and the kinds of organizations that have traditionally been the most progressive in California. I think that means something — that he would come in on the backs of those interests, and be more likely and willing to take on special interests who attacked him the entire campaign.”

Here, too, there’s a similarity to 2016 Trump, whose biography and lack of credibility with movement conservatives spurred him to make extravagant promises — like that he’d choose his Supreme Court nominees from a prereleased list — to win them over.

Similarly, the bet from some progressives is that these wealthy candidates will feel that, to make amends for their wealth, they’ll have to work even harder to prove their left bona fides. After all, there are worse things than having a billionaire owe you a favor.

Whether Democratic voters will actually be won over by this logic is of course a different question, which will depend on the dynamics of each particular election. But so long as our campaign finance system remains broken, the fantasy of a billionaire savior will remain a tempting one.