Checking in on The Free Press

Bari Weiss's media company is running out of purpose

Author

Peter Shamshiri
April 24, 2025

I understand that it isn’t healthy, but one of my favorite pastimes is checking in on The Free Press, Bari Weiss’s media outlet. 

Weiss launched The Free Press after loudly resigning from the New York Times in 2020. The outlet’s organizing principle was that mainstream media has been captured by powerful and misguided cultural forces on the left. Enter The Free Press, to restore journalism to its former glory and so forth.

The problem they face is that their brand is predicated on directing overwrought skepticism toward the left and childlike credulousness toward the right. That may have worked in 2021, when it could be pitched as a sort of half-baked contrarianism. But now, with the Trump administration embracing overt authoritarianism, it’s a little embarrassing. 

So what becomes of an outlet like this? Do they keep up the veneer of independence and contrarianism, or do they establish themselves as permanent members of the right? I will try to answer that by offering you a sampling of their content across three topics: free speech, critical coverage of Trump, and the story of Kilmar Abrego Garcia.

Free Speech

Free speech is one of The Free Press’s marquee issues – they have an entire section of their website dedicated to it. Here is a comprehensive list of the stories in that section since Trump’s inauguration:

That’s it. Every single story that takes a firm position is about purported suppression of speech by the left. When the threat to speech comes from the right, The Free Press either doesn’t cover it, or covers it in the form of a debate. 

The outlet’s coverage of Trump’s attacks on academia (which it does not include in its free speech section) has been similarly muddled. It consists mostly of straightforward reporting that’s remarkably credulous about the administration’s claims that its actions are designed to combat antisemitism. Their story about Trump’s threats to cut all of Columbia’s federal funding, for example, includes an aside that “the college has done little to root out the problem [of antisemitism],” implicitly validating the administration’s attacks. (The Free Press does not distinguish between anti-genocide protesting and antisemitism – the same piece lists the occupation of Hamilton Hall as an example of antisemitic conduct). 

By contrast, just before Trump’s inauguration The Free Press’s managing editor was describing Facebook’s fact-checking system as a level of censorship that “chilled me to my bones.”

There’s not much you can say about this that isn’t obvious. Amidst the most overt assault on speech in generations, The Free Press has yet to conjure the alarm it managed when a social media website tried to limit the spread misinformation on its platform.

Criticism of Donald Trump

The Free Press isn’t unwilling to publish criticism of Trump. That said, their standard approach is to relegate that criticism to debate-style pieces where multiple writers weigh in. Sometimes they use the debate format when there’s no real debate to be had. Recently they published a piece titled “Is Donald Trump Breaking the Law? Seven Experts Weigh In.” Here’s an excerpt:

Many critics argue that the administration’s actions stretch the limits of executive power. Others argue that they are outright unconstitutional.

The Trump White House and its defenders say that this is hysterical—and that the president is only using the powers of the presidency arrogated since the Obama administration. In the case of deporting illegal immigrants, to choose one example, they say he is doing nothing less than restoring the rule of law that the Biden administration flouted.

We decided to ask seven of the sharpest legal minds in the country from across the political spectrum—including a Bush White House lawyer, a progressive constitutional scholar, and a former federal judge—one simple question: Is the Trump administration acting lawlessly?

You might think based on that headline and this framing that some of those seven experts think that Donald Trump is not breaking the law. But not one of them takes that position. Instead, the experts they speak with break down into two broad categories: progressives and centrists who think Trump is unequivocally breaking the law, and conservatives who avoid the question but nonetheless criticize Trump.

Michael McConnell, a conservative law professor, says that the administration is “sabotaging itself with its unbridled hostility toward the courts.” Ed Whelan, best known for using Zillow in an attempt to exonerate Brett Kavanaugh, ignores the question and complains that Trump is undermining himself by merging law and politics. Jonathan Adler, another conservative professor, says that Trump is “asserting authority denied by the Constitution, disregarding legal constraints enacted by conference, and thumbing its nose at judicial orders.” 

It really seems like The Free Press set out to find credible experts willing to argue that Trump isn’t acting lawlessly, and couldn’t find a single one. That itself is an interesting story. Instead of running it, they opted to frame the issue as an active debate.

Kilmar Abrego Garcia

Maybe the most egregious piece I’ve read in The Free Press is about Kilmar Abrego Garcia, the man mistakenly deported to a Salvadoran gulag. 

I assumed that there would be substantial coverage of the case: it has been the definitive story of the past month or so. But coverage of the Abrego Garcia saga at The Free Press has been incredibly sparse: from what I can gather (with the caveat that the outlet’s search function is truly terrible), there has been one full piece dedicated to the case. That piece, by Yale law professor Jed Rubenfeld, is a defense of the administration titled “No, the President Has Not Defied a Supreme Court Ruling.”

The crux of the article is this: Donald Trump was not ordered to “effectuate” Abrego Garcia’s return to the United States, he was ordered to “facilitate” it, and therefore Trump’s failure to return Abrego Garcia is not in defiance of a Supreme Court order. 

This argument is correct in the thinnest, most technical sense: Rubenfeld is right that the Supreme Court did not order Trump to guarantee Abrego Garcia’s return, only to facilitate it. The problem is that it’s obvious that the administration is not trying to facilitate Abrego Garcia’s return to the United States. Rubenfeld knows this, because he published the piece two days after Trump infamously hosted Salvadoran President Bukele at the White House, with both parties claiming that the other party had the sole authority to return Abrego Garcia. The White House has since been engaged in an extended media campaign to smear Abrego Garcia’s name, amplifying vague and unproven claims that he is affiliated with MS-13. Every honest actor knows that the administration is defying the Court’s order to facilitate his return.

Rubenfeld ignores all of this, instead making several claims that I would characterize as insane. He says “this case is not the bombshell threat to due process that Trump opponents are claiming. Garcia has had a lot of process—several different immigration hearings.” That’s true, except that he did not receive any process in this case; he was sent to El Salvador without a hearing, which is the pertinent point. You don’t get to bank due process that someone received in other cases in order to deny them due process in the future. 

Rubenfeld also says “Contrary to what you may have read, this is not a case where the administration is claiming a right to deport anyone it chooses without ever giving that person a right to be heard.” This is the difference between me and a Yale Law professor: when the government deports someone without a right to be heard and says that nothing can be done and that they should suffer no consequences, I think it’s safe to say they’re “claiming a right” to do exactly that.

In short, The Free Press has ignored the substance of the Abrego Garcia case almost entirely, opting to focus instead on legal technicalities – and then gets those wrong, too.

Journalism like this fascinates me because it’s predicated on what should be an obvious lie: The Free Press is clearly not independent or non-partisan. It’s conservative. Its investors aren’t media types interested in funding new journalism, they’re right-wing megadonors like David Sacks and Marc Andreessen. Their readers are almost entirely right-wing (the comment section on the average Free Press article is what I would describe as “New York Post commenters with undergraduate degrees”). 

So why the charade? Why posture as independent and unbiased only to publish a slightly modernized National Review? I think the answer is that in 2020 it seemed to a lot of people – Bari Weiss included – that conservatism needed a rebrand. They bristled at the perceived excesses of the left, but they were embarrassed by the gauche anti-intellectualism of Donald Trump. So they tried to forge a third way, branding their conservatism as a sort of post-ideological truth-seeking. 

Under a second Trump administration, that brand has very limited utility. It serves mostly as a way for well-to-do conservatives to reassure themselves that their reactionary tendencies stem from something more respectable than the base bigotries and conspiracism of the MAGA movement. But Trump’s politics don’t allow room for nuance or equivocation; all things must be subjugated to him. Over time, all of the right-wing “free thinkers” will find their thoughts consolidated under his banner.

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