Donald Trump’s campaign was shaped in large part by the stories and narratives of the online right. So you’d think that after years spent doggedly proclaiming their heterodoxy and warring against the supposed tyranny of the woke mob, some of our most prominent right-leaning alt-media pundits—like Matt Taibbi, Glenn Greenwald, and Bari Weiss—would be feeling pretty satisfied. After all, they finally have a president who promises to combat the deep state and fight against the liberal elite. What’s not to love?

Not so fast. Facing a world where people in the White House will be listening to them, these self-styled iconoclasts and rebels are caught in a bind. They’ll need to address the contradiction between their images as scourges of the establishment and the uncomfortable fact that the most powerful people in the world are listening to their messages.

As I write in my new book, Owned: How Tech Billionaires on the Right Bought the Loudest Voices on the Left, these online personalities—who built their brands off the credibility of their past work as journalists—are like sharks. But instead of needing to hunt to live, their drive to survive comes from arguing with people. Faced with a president who has been willing to rhetorically adapt many positions advocated for, in one way or another, by this specific media sphere, there’s not much to bounce off. And for reactionaries whose brand is built on contrarianism, that’s a problem. With the shrinking of social media platform audiences and the targets that come with that environment, they’ve begun to turn their teeth on each other.

Thus far, Weiss seems best equipped to take advantage of the contradictions of the new regime. Her website, The Free Press, is booming, fueled by ideologically motivated investments from Silicon Valley movers and shakers like Marc Andreessen. The outlet raised $15 million in 2024 from a funding round that valued it at $100 million; as Axios reported, investors included Allen & Company founder Herbert Allen Jr. and Starbucks founder Howard Schultz, as well as seed capital from Andreessen and fellow right-wing billionaire David Sacks. Weiss’s smug self-regard—as summed up in a December 28 post on X—is endless.

“The Free Press began as a question I asked myself after resigning from The New York Times,” Weiss wrote. “Is there still a market for real journalism? For fearless, fair, independent journalism that treats readers like adults? Journalism that presents the facts—even the uncomfortable ones—and allows people to draw their own conclusions? Journalism that pursues the truth?”

No surprise that “real journalism” is the kind found at her outlet. Billed as a moderate alternative to the extremism of the right and the left, The Free Press instead launders an extremist agenda to its audience. Just over the past few months, Weiss has promoted far-right narratives about immigrant “grooming gangs” in the UK, boosted Christian zealot Seth Dillon, founder of the conservative satire site The Babylon Bee, and leaned into the anti-woke politics that made her famous in the first place. She’s also found time to maintain her connection with her real audience, the rich tech benefactors who fund her work, giving softball interviews to OpenAI founder Sam Altman and immortality-obsessed venture capitalist Bryan Johnson.

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And now, with the GOP ascendant, Weiss’s Free Press is trying to horn in on the state media territory once claimed by Fox News, interviewing House Speaker Mike Johnson, hosting events with Republican lawmakers, and scoring interviews with Cabinet members like EPA head Lee Zeldin. Weiss’s mission is transparent. But to casual politics followers and media consumers, it’s less clear. Couched in a reasonable tone and delivered by smart sounding people, the radicalizing message of The Free Press is going to be lost in the shuffle—and Weiss will be able to triangulate herself and her outlet as a counter to the excesses of Democratic identity politics and Trump both.

Taibbi, on the other hand, has left behind even the pretense of independence. The one-time Rolling Stone writer who made his name in the late 2000s by taking on the excesses of financial capitalism—including coining the description of Goldman-Sachs as a great vampire squid consuming everything in its path—has now, in late middle age, settled into a role as a conservative culture warrior.

In late September, Taibbi joined with a diverse group of right-wing cranks and snake oil salespeople at the “Rescue the Republic” rally in Washington. Sparsely attended and boasting names like Taibbi, Tulsi Gabbard, Russell Brand, Jordan Peterson, and other right-wing influencers, the event was something of a coming out party for MAHA—Make America Healthy Again, the Robert F. Kennedy Jr.–inspired movement that is ascendant under Trump. In his remarks, which were dutifully republished by The Free Press, Taibbi complained about groupthink on the left, a reliable applause line from the crowd he appeals to today.

“I grew up a liberal Democrat and can’t remember having even most of the same beliefs as my friends,” Taibbi said. “Now, millions of alleged intellectuals claim identical beliefs about vast ranges of issues.”

Two months later, on the eve of the election, Taibbi worked with Glenn Beck’s The Blaze on an article reliving his Twitter Files reporting. The collaboration is a long way removed from Taibbi’s describing the conspiratorial Beck as a “screeching media dillweed” in these pages back in 2011. These days, he’s working with the right-wing thought leader to regale an eager conservative audience with tales of “Making history in Elon’s war room.”

Taibbi’s decline strikes journalist Sana Saeed, a media critic whom I interviewed extensively for my book, as notable for how far he fell. And his shift to the right doesn’t leave many options; he doesn’t have much of a future in a Trump administration. With nothing original to say and no credibility left to leverage, there’s nothing right-wing audiences get from Taibbi they can’t already get from conservatives they already trust. Even Elon Musk, who gave him access to the Twitter Files in the first, wants nothing to do with him, but the connection to the tech billionaire continues to tail Taibbi.

“He allowed himself to become a collared dog for one of the most wretched billionaires who feels comfortable enough doing a Nazi salute at the inauguration,” Saeed said when we talked for this article.

Frankly, his newly right-wing politics aside, the thing that strikes the reader about Taibbi more than anything else is that he’s virtually out of new ideas. It’s not just going back to the Twitter Files well—two years later—for Glenn Beck’s magazine. A sampling of his recent posts on X show that the hits are all he’s playing. It’s all reactionary politics, all the way down. The self-proclaimed free speech warrior is joyful that Trump’s White House has banned the Associated Press over the outlet’s refusal to follow the president’s renaming of the Gulf of Mexico. “The once-great AP became journalism’s word police, and humorously is now claiming to be a victim of censorship,” Taibbi tweeted to promote the article. To put it lightly, his conception of censorship is subjective. “I tend to focus on one issue at a time, and digital censorship to date (though it may change) is almost 100% a Democratic problem,” he posted on X January 9. “In the last eight years, they’ve sucked more, by a lot.”

It’s redundant to point out the myriad threats to free speech originating from the GOP, but party leaders have cheered on the crackdown on student protesters, with Trump even calling to deport them, and multiple Republican-led states have passed laws barring the boycotting of Israel in a blatant violation of the First Amendment. In Florida, Republican Governor Ron DeSantis advocated for and signed a bill blocking teachers from acknowledging same-sex relationships. Trump’s war on the press, using lawsuits to silence and extort networks like ABC, may just be starting, as evidenced by how the White House Communications Office is treating outlets like the AP that it deems insufficiently sycophantic. That doesn’t seem to matter to Taibbi, who, by now, has decided that his real enemy is liberals and the left and their intellectual decline—and that it’s his sovereign duty to fight back.

That’s not unlike Greenwald, whose antipathy to liberals has arguably become the animating force of his politics. He has targeted Representative Alexandria Ocasio-Cortez, whose rise he initially championed, for her fear during the January 6, 2021, Capitol riot that she might be killed or worse. That Ocasio-Cortez became a reliable Democrat in the intervening six years since her first election is frustrating to many people who supported her; Greenwald’s specific and relentless harassment, however, is unique and elevated coming from a public figure.

In the world Greenwald lives in, the danger of liberals and Democrats to free speech, often exemplified in their desire for more moderation on social media sites, is omnipresent. To listen to him tell it, “Online censorship began in earnest after 2016 with the dual traumas of Brexit and Trump. Western power centers concluded they could no longer trust free speech online, so they concocted this fraudulent ‘disinformation’ expertise and industry to masquerade censorship as science.”

To the extent that this version of reality may have a ring of truth—at least inasmuch as one of the reactions to Trump’s first election was to look for ways to blame Russia, social media companies, and whatever else rather than a failure of institutions—it overemphasizes the role of these governments in promoting what’s a questionable at best censorship regime.

The TikTok ban was a perfect example. “It’s Trump, almost alone in DC, fighting to keep it open,” Greenwald tweeted January 19, setting up the incoming president as a warrior for open discourse. The reality, that Trump was doing it to enrich his donors and ensure that ownership was at least partially in the hands of billionaire allies, went unmentioned. The president has been clear that his policy, like Biden’s, is to deliver at least some of the company to a friendly American investor. And Trump ally Jeff Yass, a billionaire businessman, has a lot of money in TikTok parent company Bytedance already, giving the president another reason to stay the order of execution (that he himself originally attempted).

But leaving that kind of information out isn’t new for Greenwald. To Robert Mackey, a former colleague of Greenwald’s at The Intercept—they overlapped from 2016 to Greenwald’s departure in 2020; Mackey stayed on until 2022—the pundit’s role as a polemicist has always chafed. Greenwald has often appeared to Mackey as less interested in truth than in score settling.

“I also was a high school debater, as he was,” Mackey told me. “And I think that I understand that way of approaching things—you’re really only interested in information that helps you.”

Such information is often broadcast to Greenwald’s audience via Rumble, the conservative YouTube clone that benefited from a funding round led by Peter Thiel and JD Vance in May 2021. The capital raised went to expanding the platform’s reach and enticing right-wing online influencers to bring their shows over  to the site—including Greenwald, who signed just months later. Today, his System Update show airs regularly and he uses it to rail against liberal censorship and Democrats, as well as, occasionally, the right. On February 11, Greenwald had Matt Stoller, a fellow lefty-turned-righty, on to bemoan the Trump administration’s gutting of the Consumer Financial Protection Bureau, as if this was a surprise.

From a cynical point of view, Greenwald’s taking shots at both sides has a lot of utility for his career. By focusing his critique on the idea of the government as a malign influence, he allows for some wiggle room in whom he attacks and how; unlike Weiss and Taibbi, if Trump fails, Greenwald can claim distance from the administration and its mission. This is probably best seen in his continued, and principled, opposition to Israel’s treatment of the Palestinians. It’s an issue that Greenwald has seldom if ever wavered on during his career in the media and one that tends to align him with the left, making his political positioning hard to pin down for observers. In fact, he often criticizes Weiss over her hawkish positions.

Liberal hysterics about the threat of Trump and Democratic support for the national security state make him a good messenger for the right, and it’s one way he can get to members on the left who share his anger over Gaza and his general disdain for the more mainstream of the Republican Party—not to mention his role in breaking the NSA spying scandal in 2013.

But that anti-establishmentarianism is running up against the realities of whom the establishment now constitutes. When Trump, after calling for US involvement in Gaza, escalating saber rattling with Iran and China, and musing about invading Greenland and/or Canada, made an offhand remark about cutting the military budget, Greenwald took to Twitter to crow, “Those who failed or refused to see the massive opportunities from this Trump-led realignment—and instead enslaved themselves to the broken, ossified, unimaginative, status-quo perpetuating Democratic Party—are some of the dumbest people on the planet.” The commentary paid off; Greenwald was invited on Fox & Friends to praise the president the following Sunday. Unmentioned was the fact that the “cuts” Trump has proposed will simply reapportion those funds to the president’s priorities, including an “Iron Dome” for America. Hardly a realignment.

It’s hard to be an alternative when the mainstream is people you support. Rebranding as a mouthpiece for the new establishment is a tricky business when your appeal is independence. But faced with a world where some of the most influential people on the planet are their allies, Greenwald, Taibbi, and Weiss are largely choosing to cozy up to power rather than effectively challenge it. No big surprise.