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.