Five years ago, in the epistemic fog of early Covid, Trump 1.0, George Floyd, and the attendant cultural inflection point, the New York Times Opinion columnist Bari Weiss defiantly announced that she was resigning from the paper in protest of its illiberal ideological intolerance. In a public letter, she accused publisher A.G. Sulzberger of abandoning the paper’s commitment to a free exchange of ideas and caving to a progressive mob, including Times staff who bullied her for her heterodox—pro-Israel, anti-D.E.I.—viewpoints. “Nowadays, standing up for principle at the paper does not win plaudits,” she wrote. “It puts a target on your back.”

Weiss’s cri de coeur may have been a little ham-fisted, but she wasn’t wrong. Sulzberger, a principled and extremely thoughtful steward of his family’s heirloom, had indeed reversed his decision to back Opinion editor James Bennet in the wake of the infamous Tom Cotton editorial—eventually defenestrating the guy after it was clear Bennet had lost the room amid a staff revolt. The victimhood shtick may have irked some of Bari’s former colleagues, but her defiance of liberal orthodoxy and the mainstream media resonated with many—especially the nation’s corporate titans who, despite their power and influence, seemed annoyed by the rise of a woke progressive hegemony that demanded allowance to protest authority, state their pronouns, and work from home.

Indeed, this C-suite crowd, which was already bitching about the Times and even had a few nits to pick with the Journal, fell hard for Bari’s politically fluid brand of anti-woke, pro-free-speech cultural commentary. Unlike Sulzberger, they didn’t want to appease the sensitivities of the people who worked for them. No, they wanted those people to rein in their inner selves, largely shut the fuck up, stop Zooming in from Lake Arrowhead, and not feel emboldened to take personal days when their cats got food poisoning. The pendulum always swings, and Weiss perfectly timed the reversion to a pre-Trump, anti-thought-police era that so many others have subsequently raced to monetize.

Not long after launching her own Substack—first called Common Sense (not to be confused with Jim Steyer’s very successful media advocacy enterprise), then The Free Press—Bari began taking investments from Marc Andreessen, David Sacks, Bobby Kotick, Howard Schultz, and others who delighted in hosting her at private dinners and listening to her speak onstage at the Allen & Company conference in Sun Valley. In the meantime, The Free Press grew into a veritable business. Bari hired similarly provocative writers like Niall Ferguson, Eli Lake, and Matthew Continetti. More recently, she brought in a president-publisher, Dennis Berman, a former Journal reporter who took a spin in corporate life at Lazard; and a growth officer, Daniel Hallac, to manage and let Bari be Bari. According to a source familiar with the numbers, The Free Press is now nearing 1.4 million subscribers, of which nearly 170,000 are paid—a figure that would equate to around $13 million to $14 million in annual subscription revenue. The politically charged content is unlikely to ever ignite a scalable advertising business, but Weiss’s stardom offers other revenue channels.

Now, unsurprisingly, the darling of the Sun Valley set has become a coveted acquisition target for some of its members. In recent months, both Lachlan Murdoch and Skydance chief David Ellison have looked at deals with The Free Press, though only the latter seems to be pursuing it in earnest. Late last year, amid his pursuit of Paramount, David met with Bari and, according to Status’s Oliver Darcy, pitched her on a role at Paramount’s CBS News. Last week, amid a Times report about acquisition talks, David met with Bari and her lawyers in Sun Valley to discuss the broad outlines of a deal. Those negotiations are in early stages; a source with knowledge of the talks described them as “very, very premature.”

On one level, David’s pursuit of The Free Press feels like a passion play, a chance to virtue signal to his fellow media executives (and Trump) and tack CBS News toward something less overtly liberal. Jeff Bezos, for his part, seems to be attempting something similar at The Washington Post, though you really need a magnifying glass and Morse code to deduce any sort of strategy there. Anyway, like many in that crowd, Ellison was also smitten by Bari’s unwavering support of Israel and preoccupation with the rise of antisemitism—issues that are as near and dear to David’s father, Larry, as they are to Paramount’s outgoing owner, Shari.

Indeed, as I’ve noted before, for all the sturm und drang over the 60 Minutes Kamala interview, Shari’s true frustrations with CBS News stemmed from her anger over what she perceived as anti-Israel bias. When anchor Tony Dokoupil was admonished by CBS News execs for a hard-hitting interview with the avowedly pro-Palestine Ta-Nehisi Coates, Bari chastised his bosses and was the first to publish the humiliating audio recordings of an internal meeting showing how they’d mismanaged the fallout. (Both the executives involved have since resigned.)

At the same time, there is a strategic rationale for a Free Press acquisition. Like most television news networks, CBS News lacks a real multiplatform digital presence. The Free Press, already one of the largest businesses on Substack, would immediately put Skydance in the newsletter-and-podcasting game, which it could then scale further. Indeed, one media analyst estimated that Skydance could easily double the revenue of The Free Press with the support of the CBS ad sales team. Meanwhile, Bari’s presence as a spiritual advisor to CBS News—not as a manager, which is also not her strong suit—might at least inspire some curiosity around the network.

On the other hand, acquiring a politically charged, nascent media brand that recently announced a $100 million valuation would seem like a bizarre distraction for a guy attempting to finally consummate an $8 billion deal, all with Jeff Shell waiting in the wings to find billions in synergies. Why should Skydance spend an iota of time doubling a modest eight-figure revenue line given the tasks at hand—saving or selling the cable portfolio, preserving the relevance of CBS Sports, laying off zillions of people, and protecting Paramount, all while Cheddar-izing CBS News with the exemption of 60 Minutes? Any deal would bestow generational wealth on Bari, but it might seem like a red herring to those existing Class B Paramount investors contemplating lawsuits.

Meanwhile, Bari’s arrival at Skydance might be anathema to veteran CBS journalists who would resist the association with her politics. Though, as I’ve noted, their pique over any sort of reputational damage may be evidence of their own myopia, and precisely the sort of groupthink that forced Bari to launch this endeavor in the first place. And it’s not like they have a ton of other options. As the fallout from the 60 Minutes settlement has proven, this cohort has outrage aplenty, but they’re pretty practical about their own personal economics.

Would Bari be wise to take David’s money? Duh. Even if Weiss is still on her unfettered ascent, The Free Press succeeds by offering brand affiliation for well-educated centrists who feel adrift and resentful in the chasm between Fox News and The New York Times—a poignant, if likely fleeting, moment. And then there are the key person challenges. Ferguson and Continetti may be good writers, but The Free Press is Bari World. What happens if she gets bored or rich or something else? It’s a reality that will likely chill some investors.

Nevertheless, a deal would be a triumph for the creator economy and the latest indication of just how profoundly the media landscape has changed. Twelve years ago, Bezos spent $250 million for the sprawling, century-plus-old Washington Post. Three years ago next month, the far smaller challenger brand Axios sold at a $525 million valuation. Would Ellison cut a low-nine-figure deal for Bari World? The very possibility, of course, merely outlines the challenges he will face at Paramount: Post-monoculture media is getting more and more niche-ified, talent-oriented, and authentic. Then again, maybe Bari could be his spirit guide through this new world.