The Irony of Pierre Omidyar

Pierre Omidyar in 2010
Photo by Ramin Talaie/Corbis via Getty Images
Theodore Schleifer
July 22, 2021

In a tech culture generally teeming with boisterous and astronomical billionaires, it’s been rather easy to forget about Pierre Omidyar, the reclusive eBay founder, worth $25 billion, who helped jumpstart the careers of loudmouths like Elon Musk and Peter Thiel when he bought PayPal nearly twenty years ago. Omdiyar has largely fallen off the map since his $250 million adventure into media, which included memorable dust-ups with Glenn Greenwald and Matt Taibbi. He hasn’t tweeted since 2019, when he locked his account after years of quotidien anti-Trump messages. Instead, he and his wife, Pam, have busied themselves overseeing a multi-billion dollar philanthropic empire from a remote estate outside Honolulu, where Omidyar keeps his Gulfstream G650 and a small security force. “I do like to fly under the radar,” he said in a rare 2009 interview.

But Omidyar is quietly on the cusp of an ironic reemergence. Despite making extraordinary wealth from the internet, he has recently become a leading funder of the “hipster antitrust” movement currently sweeping K Street and Pennsylvania Avenue that seeks to break up companies like Facebook and Google. It’s a peculiar position for someone of Omidyar’s bearing. One of the iconic business leaders of the first tech boom is now spending his money to defang the winners of the second.

Omidyar’s transformation into a trustbuster is an unexpected turn from his past life as a lanyard-carrying neoliberal, more at home among Clinton Global Initiative panelists than the progressive agitators who now make up Biden’s left flank. Over the last 20 years, he and his wife have given away more than $3 billion to various endeavors, including through a “philanthropic investment firm” called the Omidyar Network that believes that “market forces can be a potent driver for positive social change.” People who worked with the Omidyars during the dot-com boom recalled an overwhelmed, new-money couple drawn to the notion of “venture philanthropy,” as advocated by friends like Jeff Skoll and Steve Case—the idea that socially-minded enterprises, powered by the motor of capitalism, can do great things for humanity. The strategy was faddish, and Omidyar became the era’s leading proselytizer: his most prominent bet on that theme was with Muhammad Yunus on microcredit loans, a play that is widely judged to have been underwhelming. Despite all his energy and money, clear wins were hard to find.

For as long as a decade, some staffers were “frustrated” that Omidyar, who has always been an avowed skeptic of political power, had shied away from issues of corporate power, a source close to the Omidyar effort told me. “They didn’t know what the principal wanted,” this person said. “And Pierre was busy at the time.” In 2018, however, Omidyar blessed a sharp leftward turn, leaning into a faddish-again thesis that used philanthropy to empower government. Omidyar appointed a new C.E.O., Mike Kubzansky, who made two of its three focus areas “reimagining capitalism,” a euphemism for a stronger public sector, and “responsible technology,” a cognomen for scrutinizing Big Tech. Omidyar Network is now widely seen as among the most progressive philanthropies in the business, even if its patron hasn’t shed his technocratic roots. “I do think there’s been a journey from being techno-optimist to techno-realist,” one person close to Omidyar said of the billionaire, who, decades after creating eBay, now sees internet platforms as a threat to democracy.

Many of the leading lights of the antitrust movement can now trace their trajectory back to an Omidyar check: The Open Markets Institute, which Omidyar funds, helped produce Joe Biden’s new head of the Federal Trade Commission, Lina Khan, and is close with Tim Wu, who Biden named to a key antitrust role inside the White House. Over time, Omidyar’s team has hired former antitrust lawyers, authored closely-read policy papers, and funded so many groups that his team has even had to settle tribal dustups within the fiefdom. When several of these Omidyar-funded groups were about to “chew each other’s heads off” as they squabbled over the response to the series of antitrust bills that Congress is debating this summer, Omidyar’s team stepped in to cool down tempers and steer the movement’s response, a person involved recounted to me.

The eBay baron is suddenly ascendant in Washington. “If they put Jonathan Kanter into the AAG spot, then, honest to God, they’re gonna have to put a statue to Gus and Pierre in the Statuary Hall at the Capitol,” one of those antitrust rabble-rousers told me last week, referring to key Omidyar aide Gus Rossi. On Tuesday, Biden indeed nominated Kanter, another tech industry foe and friend of OMI executive director Barry Lynn, as Assistant Attorney General for Antitrust at the Justice Department.

A statue might be overstating Omidyar’s influence—there are a small number of other antitrust donors, including fellow Silicon Valley apostate and Facebook cofounder Chris Hughes, andOmidyar is still not involved in day-to-day operations at his eponymous shop. Kubzansky calls the shots and sets the direction. Talking to people who have worked alongside Omidyar and his aides over the last week, I get the sense that Omidyar, for all of his tweets, still doesn’t really want to be directly involved in the sort of headaches that occur in the grim underbelly of the swamp. “We could get a lot more done if Pierre would call Mitch McConnell and Chuck Schumer,” said one person who advises his team on politics. “But he’s like, ‘Nope.’ He is not a game player. He is not interested in that.”

Still, Omidyar has approved this more political orientation for his philanthropy of late, setting aside the kumbaya, good-government bromides in exchange for an explicitly anti-monopoly agenda. “We all evolve agewise,” said one person who is close with the Omidyar family. “Your experience takes you to different places at 50 than where you were at 30.”

In some ways, the French-born, mild-mannered Buddhist is among the most subversive of the Silicon Valley billionaires I have covered. Omidyar criticized Barack Obama from the left for his surveillance dragnet, funded six years of Greenwald’s splenetic journalism career, and is now asking uncomfortable questions about the capitalist system that made him rich in the first place.

And yet for all his lefty mores, Omidyar is not someone who comes to mind if you’re asked to list the great political machines of Silicon Valley. That’s because Omidyar has always tried to present himself as above partisan politics—the kind of donor who focuses narrowly on transparency, media literacy, and voter empowerment that “strengthens democracy,” and then lets the chips fall where they may. There is certainly a class of Democratic operatives who think this type of hands-off, let-the-people-decide approach to American politics is hopelessly romantic, even naive. More charitable interpreters cast his ideology as merely enigmatic. “Our support for a strong democracy is aimed at protecting democratic institutions, systems, and values and not at supporting specific candidates or political parties,” he wrote on his personal blog in 2020, ruling out donations to any candidate in the 2020 cycle (a tradition that he said dated back to 2011.) In that same blog post, Omidyar took the unusual step of disclosing the $17.5 million in dark-money contributions he had made to 501c(4) organizations in 2019. From my years covering campaign finance, I can’t overstate how rare it is to see a donor voluntarily disclose this information.

Of course, transparency only goes so far. The Omidyars published a new blog post revealing another $62 million in election-year contributions only after I asked his team for the annual disclosure he promised. Plus, most of which Omidyar donated last year went to a group called the Sixteen Thirty Fund, a shadowy pot of money that in turn distributed about $60 million into Democratic super PACs in 2020. Part of the appeal of these pass-through entities is that they allow mega-donors to effectively write checks to super PACs anonymously, skirting the disclosures that are required when donors contribute to a super PAC directly. We’ll never know the full roster of the Fund’s backers, which is one of the greatest mysteries in big-money politics, but we are now aware that the Omidyars are among its most prodigious supporters. Their blog post disclosed a donation of $45 million to the Civic Action Fund, a now defunct effort that was a project of the Sixteen Thirty Fund.

I am told that the Omidyar money largely focused on voter registration projects. In other words, Omidyar didn’t secretly exploit the loophole to write a check intended for Biden-backing super PACs like Priorities USA. But the line between political nonprofit work and partisan campaigning can be awfully thin. And anyone who tells you that they know exactly how the Sixteen Thirty Fund operates is lying. (A person involved with the Sixteen Thirty Fund, in an effort to disabuse me of my curiosity, told me: “If the Sixteen Thirty Fund worked the way that the Koch network works, we would have won by a lot more.”)

In 2019, the Omidyars disclosed that they gave the Sixteen Thirty Fund $7 million. That made them the sixth biggest donor to the group that year, according to its tax filing. We don’t yet have a 2020 tax filing, but it’s safe to say that the $45 million the Omidyars donated last year probably puts them at least in the same ballpark and makes the couple one of the biggest progressive donors in the country.

At the age of 54, Omidyar is finally playing the game, in his own way. Of course, if Big Tech survives Biden’s trustbusters, then Omidyar’s political rebirth may read like just another misadventure. But he is, for now, an underrated power player, proving there’s another model to political influence that his louder friends at Democratic super PACs might be keen to learn from.