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In 2021, the Hollywood producer Brian Grazer was on a bike trip in South America with some friends, including media mogul Barry Diller, former Allen & Company president Herbert Allen Jr., and former Activision chief Bobby Kotick. A registered Democrat at the time, Grazer was expressing his frustration with the woke fever gripping the country and was considering holding a salon at his Santa Monica home to discuss the issue. Allen suggested Grazer get in touch with his son Herb Allen III, who now runs the family’s boutique investment bank, which is known for its billionaire-heavy media-tech confab, held each year in Sun Valley, Idaho. When Grazer spoke to the younger Allen, he said, “You should talk to Bari Weiss.”

Weiss had recently arrived in Los Angeles from New York, a city she’d left behind in 2020 along with her job editing and writing for the New York Times’ “Opinion” section. Although Weiss technically left of her own volition — blasting the paper for its “illiberal environment” in her publicly posted resignation letter — it felt as though she had been hounded out in the wake of the Tom Cotton op-ed fiasco, during which her boss, James Bennet, had been forced to step down amid a newsroom revolt. Grazer invited Weiss and her partner, the then–Times journalist Nellie Bowles, to his home, as well as some friends including Kotick, New England Patriots owner Robert Kraft, and Warner Bros. Discovery CEO and president David Zaslav. Weiss knew Kraft only vaguely through Columbia Hillel and didn’t recognize Zaslav at all. She had never met Kotick, who would become a key investor in the Free Press, the news and opinion site she and Bowles would launch on Substack in 2022. But her naïveté was part of her charm — as was her evident talent. “She struck me as someone with moneymaking DNA,” said Kotick.

In the years since, Weiss, now 41, has gone from meeting moguls to becoming one. She turned her anti-woke, anti-elite, and often MAGA-tolerant newsletter into a full-fledged media company, then sold it in October for $150 million to David Ellison, the 42-year-old chairman of newly consolidated Paramount Skydance. As part of the deal, Weiss became the editor-in-chief of CBS News — the kind of legacy outlet she burnished her name railing against. Only a few years earlier, as a mid-level editor at the Times, Weiss had expressed anxiety to colleagues about asking for a $10,000 raise. Now she has returned to New York as one of the most powerful and well-remunerated people in all of media. “Coming out west to get your fortune is kind of a timeworn tradition,” a friend of Weiss’s said. But as Broadway producer and media strategist Alex Levy, another friend, put it, “Bari did not set out to get rich. She set out to make an impact. And the rich is just incidental to that.”

The move to L.A. was essential to Weiss’s reinvention. If New Yorkers had cast her out under a hail of jeers, Angelenos embraced Weiss for a variety of reasons, not least because, in this industry town, journalists are exotic animals. “You go to a dinner, and you’re automatically the most interesting thing in the room because you don’t do the thing that they do,” said one L.A.-based writer. But her main appeal was politics. While the kings of Hollywood were struggling to understand the activist energy and eat-the-rich mentality infiltrating their studio lots and workplaces, Weiss — a Columbia-educated, Times-credentialed gay woman who cried when Donald Trump was first elected — validated their concerns that this had all gone too far. People wanted her at their dinners and events. “She kind of became this party trick for wealthy Westside executives who wanted to have a certain kind of conversation that they thought they couldn’t have in public,” said one media executive.

Pledging to support the Free Press, whether or not they actually read it, became a statement in and of itself for erstwhile liberals in California dismayed by what they saw emanating from the woke centers of New York and Washington, D.C. The allegiance to Weiss only deepened after October 7, 2023, when pro-Israel contingents grew even more exasperated with the mainstream media for failing to cover the subsequent war to their........

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