Ben Schreckinger is a reporter for Politico.

On a recent Friday afternoon, in a private room at a steakhouse in midtown Manhattan, the bankers at Scarsdale Equities, a boutique investment firm, were talking politics when their conversation took an untraditional turn.

Several participants claimed over their porterhouses that the only “serious” candidate in the 2016 race was Gov. John Kasich, Republican of Ohio. Then, one of them turned to chief operating officer and known liberal Wade Black. “Wade, do you feel the Bern?” the investor teased him. “Are you a Bernie supporter?”


“Yeah,” said Black. “I am.” The startling admission drew snickers.

“They said ‘Oh, he’s going to bankrupt the country.’ I said, ‘Do you actually know what you’re talking about?’” recounts Black. “They probably never met anybody who was a Sanders fan.”

Even by the standards of high finance, Black, 41, can claim membership in an ultra-exclusive club. He belongs to a small minority defying stereotypes and shattering taboos across New York City’s finer eateries and trading pits this primary season: Wall Street financiers who support the presidential bid of Vermont’s self-described “socialist” senator, Bernie Sanders.

“I don’t know anybody in this industry who supports Bernie,” one financier who gave to Sanders writes in an email. “I’m not aware of anyone else who might also be a Bernie supporter,” writes another, a former financial analyst at Goldman Sachs. “Best I can tell, I am the only one,” writes a third, while confessing to being hung over from a night out with clients.

But a dive into Sanders’ donor rolls from the second and third quarters reveals that of the tens of thousands of Americans listed as contributors on Sanders’ campaign finance reports, well over a hundred work in the financial services sector. Most are west of the Mississippi at small firms and local bank branches, where Sanders’ calls to rein in Wall Street do not hit so close to home. More noteworthy are the lonely few—roughly two dozen—who work in high finance in Manhattan.

Sure they’re capitalists, but they’re also iconoclasts—Wade Black’s Twitter feed includes several retweets of the dissident journalist Glenn Greenwald and the contrarian finance blog Zerohedge. They do not worship at the altar of the market, and having seen the American economic system from the inside, they’ve come to agree with Sanders’ conclusion that the game is rigged in favor of the well connected and a handful of big banks. Some also work at small Wall Street shops that could actually benefit if Sanders succeeded in his No. 1 goal: breaking up the biggest banks.

And what they lack in numbers, these pro-Bernie Wall Streeters make up for in chutzpah: There’s a former world champion player of the fantasy trading-card game “Magic: The Gathering,” a guy named Paul Ryan and the man who oversaw legal, compliance and auditing for Lehman Brothers until its September 2008 collapse.

To the rest of the street, these people can be hard to fathom. Sure, Sanders praises entrepreneurship on the stump—local business thrived during his tenure as mayor of Burlington, Vermont, in the 1980s. And sure, there are plenty of Democrats on Wall Street. But few would call themselves “democratic socialists” as Sanders does, and that bronze bull in Bowling Green is not a tribute to universal health care. Sanders has called for breaking up the big banks, imposing higher taxes on the wealthy and waging “a moral and political war on the billionaires and corporate leaders on Wall Street.”

Which is why Fox Business Network senior correspondent Charles Gasparino—who took to the airways three weeks ago to express shock at his discovery that two brokers in Washington state listed as employees of Merrill Lynch had given Sanders a total of $3,700—tells Politico Magazine he wants to know: “When you gave that contribution, did you have a heroin needle sticking out of your arm?”

Hillary Clinton has turned up her anti-Wall Street rhetoric as Sanders has gained ground, but her husband’s administration deregulated the industry in the ’90s, and she maintained good relations with it as a senator from New York. Today, she carries the seal of approval of Goldman Sachs CEO Lloyd Blankfein. The top 20 contributing organizations to Clinton include Morgan Stanley (whose employees have given $133,000), JPMorgan Chase ($97,000) and Bank of America ($90,000). Meanwhile, no bank broke into Sanders’ top 20, which would require less than $7,700. Not a single soul currently employed by Goldman Sachs chipped in for Sanders—an impressive feat of restraint given that at least three current or former employees of the Koch brothers appear on his donor rolls.

But among the bankers for Bernie there is Steven Berkenfeld, whose role at Lehman landed him on the list of dramatis personae laid out at the beginning of New York Times journalist Andrew Ross Sorkin’s account of the financial crisis, Too Big to Fail. Since overseeing compliance for Lehman Brothers and serving as chief investment officer of its private equity division up until the firm’s collapse, Berkenfeld, a renewable energy banker who sits on the board of directors of the Sierra Club Foundation, has landed at Barclays. It is unclear whether his environmentalism, his experience at Lehman or something else motivated his contribution to Sanders. He did not respond to requests for comment.

Some of the financiers who support Bernie Sanders, like Enrique Diaz-Alvarez, the former head of proprietary trading at the French bank Sociétée Générale, very publicly break the Wall Street mold. Diaz-Alvarez, now the New York-based chief risk officer of Ebury, a firm that helps businesses hedge their currency exposure, has racked up bylines in the socialist Jacobin magazine. His Twitter profile includes a quote from “The Way We Live Now,” an 1875 satire of greed in English society.

Others let their socialist tendencies emerge more slowly. At 50 years old with close-cropped dark hair, former Harvard rugby player Paul Ryan certainly looks like a lot of other investment bankers.

Even Ryan’s name evokes limited government and the profit motive. Last week, he received an errant email from his old acquaintance Ken Mehlman, the former Republican National Committee chairman-turned-Wall Street lawyer. Mehlman, who didn’t respond to a request for comment, had apparently intended it for the Republican congressman on the cusp of becoming the speaker of the House of Representatives. The actual recipient thought about responding, “You’re talking to that other rat bastard Paul Ryan who stole my name,” but settled on a more courteous reply.

And when it comes to, say, the current Republican front-runner, Ryan, the managing partner of Hayfield Capital, certainly talks like other investment bankers: “Trump is an old, well-known shithead in the business,” says Ryan, adding that when he worked at Barclays’ real estate group 25 years ago, his boss refused to deal with the developer on account of his “slippery business practices.” (The Trump campaign did not respond to a request for comment.) Ryan adds, with a hint of admiration, “He doesn’t seem to give a fuck.”

But then Ryan starts to talk politics, and the words between the four-letter ones start to sound different. “Anyone with any sophisticated understanding of what’s going on takes that Republican free market bullshit and just calls it out,” he says. “Nobody even knows what the fuck a socialist is anymore.”

Ryan grew up in Buffalo, New York, and as an undergraduate at Harvard and banker at Barclays in the 1980s, he was sympathetic to Reagan’s pro-market message that government had grown too big. In 1992, he voted for George H.W. Bush because Bill Clinton “didn’t understand the economy.”

After Harvard and Barclays he enrolled in night classes at Fordham Law School and worked for hedge fund manager Buddy Fletcher. In 1996, he switched sides and voted for Clinton, because he couldn’t stand Bob Dole. He stuck with the Democrats in 2000. “I didn’t care for [Al] Gore,” he says. “But [George W.] Bush was a moron.”

In 2001, he founded Hayfield, an investment bank for the smaller businesses that places like his hometown—devastated by corporate consolidation and globalization—so badly need. Its website’s homepage declares, “This is not a business for aristocrats.”

Ryan says he was horrified by the quick-buck mentality that preceded the 2007-08 financial crisis. “Who would’ve put your name on this shit?” he asks rhetorically of the faulty financial products that precipitated the crisis, then explains, “The idea was people did not give a fuck, because there was no shame. You could move on.”

As the crisis was unfolding, he was becoming an enthusiastic supporter of Barack Obama. He says his perch on Wall Street is exactly what’s convinced him of the need for dramatic reform.

But Ryan says the president did not go far enough in overhauling the sector, and he decries the continued flight of capital from small business and publicly traded companies to structures like private equity firms that are both large and opaque. “If you’ve actually had a front row seat to this you can see what’s going on, and it’s not a good trend. Money gets made in the dark, and you can’t figure out what’s going until there’s a massive fuck-up.”

Seeing the pendulum swing too far in favor of unregulated markets, the onetime supporter of the Reagan revolution says he’s ready for another revolution. “I think there’s a balance, a dialectic, if you read Karl Marx, that has to pull things back towards the middle.”

Now, he’s pinning his hopes for reform on the blunt Brooklynite Sanders. “If he’s president, then he’ll probably enforce the labor laws,” says Ryan with anticipation. “Amazon should probably shit its pants.”

If Sanders loses the nomination, Ryan says he’s considering bypassing Hillary Clinton, whom he disdains as much as her husband, for the nuclear option. “I might just want to see some Republican run it and let the shithouse burn down.”

Clearly, Ryan is not shy about expressing his views, but he understands the reluctance of many in the industry to follow his lead. “For many people, I think it would be like coming out of the closet to come out as a Sanders supporter on Wall Street.”

That includes Jon Finkel, head trader at the quantitative hedge fund Landscape Capital Management. He was one of several financiers contacted for this story who agreed to interviews but then backed out.

In an email, Finkel wrote that he needed to consult with his partners about “any potential business costs to speaking on the record.” Then he declined to be interviewed at all.

But unlike others, Finkel had a second change of heart and decided to speak. He has already been outed once as a Wall Street oddity after going on a date with a Gizmodo editor who proceeded to write about his success in the world of “Magic: The Gathering,” a fantasy card game filled with magic and mythic beasts. Finkel is a former world champion, and has a Wikipedia page dedicated to his career in the game.

He says he sees no conflict between his day job and his politics. “There’s this idea that somehow there’s a disconnect between being in a profession where you’re going to be in a high tax bracket, like finance, and social justice … that’s sort of a fallacy.”

Finkel also has less to lose from reform than many of his peers. Because his investments turn over quickly, the capital gains are taxed at the same rate as regular income, and he does not benefit from the carried interest loophole, which Sanders, as well as Clinton, Trump and Jeb Bush, support closing.

Besides, Finkel does not identify strongly with the culture of Wall Street.

“I never really thought I’d end up in finance; I just backed my way into it,” says Finkel, who says he was invited to try his hand at trading by fellow Magic players who saw a connection between the skills employed by the card game and in quantitative trading: examining problems, understanding variance in the world, patience for long-term strategies.

He does not hide his socialist sympathies from the other partners in his hedge fund and says he’s even had productive discussions with his most conservative colleague. “On some level, we really do agree a lot about how the world should look and what would make the best world. We have strong disagreements on what is the right way to get there, but I think those discussions are probably very good for allowing us to see other perspectives.”

But he says he rarely interacts with members of his industry outside of his fund, except for the occasional investor gathering, where he tends to hold his tongue. “Every now and then someone will say something in an investment meeting,” he says. “Some comment about a tax rate or some economic thing, and then I don’t say anything and just move on with the meeting.”

Says Finkel: “I grew up awkward and nerdy, so I got used to feeling out of place.”

Correction: This article has been updated to correct Berkenfeld's current and former roles.