What's the Matter with Glenn Greenwald and Matt Taibbi?

Yahoo

15-04-2025

A few weeks into 2025, Ross Douthat, The New York Times' idiosyncratically conservative columnist, interviewed Marc Andreessen: Netscape co-founder, venture capitalist, general Silicon Valley gadabout, and, lately, fixture in Trump-adjacent Washington, where he has reportedly been interviewing candidates for top agency positions and promoting rollbacks of Biden-era cryptocurrency guardrails. O tempora, o mores.
In the course of the interview (the audio of which is available in full as an episode of the paper's Matter of Opinion podcast), Andreessen laments the pressures of a socially conscious press, college students, social media activists, and activist shareholders. He evokes a genuinely paranoid fantasy that tech workers were once on the verge of a violent labor uprising: Workers of the world, you have nothing to lose but your keyboards! He appears to claim that, at some point in the years 2016 to 2020, 'the federal government radicalized hard under Hillary.' It's unclear what he was referring to. The Times, in any case, removed the offending quote in its print edition.
Andreessen is far from alone in his embattled posture. A set of increasingly vocal, increasingly right-wing tech billionaires has come to share with some segments of the left (or, as we shall see, the former left) an almost obsessive concern with the hypocrisies and shortcomings of modern liberalism. Some of these figures, like PayPal billionaire Peter Thiel, have long been associated with the political right, and Thiel's 1998 attack on 'multiculturalism' in elite universities, The Diversity Myth (co-written with current Trump 'crypto czar' David O. Sacks), presaged today's great national DEI freak-out. Others were more ambiguous, political agnostics in the vast, squishy center of American politics who have only more recently drifted into the embrace of a newly dynamic right unbound by its stodgy past.
Andreessen himself long supported Democrats, but he grew incensed by the Biden administration's mild skepticism toward and willingness to regulate cryptocurrency, eventually embracing a belief that the Consumer Financial Protection Bureau and the deep state were engaged in a deliberate program to 'debank' conservatives and cryptocurrency investors. Mark Zuckerberg, who had previously cultivated a studiously apolitical public image, killed all DEI initiatives at Meta (blaming them on his departed female COO, Sheryl Sandberg) and went on the Joe Rogan show to propose a need to bring 'masculine energy' back to the workplace. Elon Musk was once a darling of liberals and environmentalists, but his various musings on 'free speech'; his chummy social media interactions with online Nazis, 'race realists,' and other such strange creatures; and, of course, his spectacular embrace of Donald Trump have disabused the center and the left of any notion that he might be on their side.
This rightward turn has drawn noisy criticism. Yet the tech barons, platform operators, and publishers had already found a new set of friendly voices in the media. As it turned out, there was a pool of ready-made scribes, who, like them, had soured on the Democratic Party, on speech codes they perceived as a regime of censorship, and on the perceived excesses of DEI, and who were eager to take advantage of the new, growing platforms that billionaires like Thiel, Musk, and Andreessen acquired or funded.
Owned: How Tech Billionaires on the Right Bought the Loudest Voices on the Left, a new book by the journalist Eoin Higgins, is an attempt to understand how a collection of unimaginably wealthy, increasingly angry titans of technology and finance were able to acquire loud allies among journalists who had, until relatively recently, been largely associated with the political left. Higgins previously covered this beat in his work for Fairness and Accuracy in Reporting and for his own newsletter, The Flashpoint. Some of that work is repurposed here, but the book expands on it, taking a broader look at the sociocultural and political currents that have brought new alignments of writers, audiences, and funders.
His two main subjects are the journalists Glenn Greenwald and Matt Taibbi, although a number of other new-media all-stars and hangers-on make appearances, most notably Free Press founder and former Times columnist Bari Weiss, who, while lacking Greenwald's or Taibbi's superstar-journalist quality, comes across as a much cannier operator with a longer and more strategic view of her project.
Greenwald and Taibbi arrived at their journalistic celebrity through different paths. Greenwald, a civil libertarian and (usually) strident critic of U.S. military and intelligence policy, cut his teeth as a blogger and Guardian columnist before rocketing to international fame by acquiring and publishing the Edward Snowden National Security Agency leaks and founding The Intercept with backing from billionaire eBay founder Pierre Omidyar. Taibbi started as a kind of new gonzo journalist—will no one free young men from the curse of Hunter S. Thompson?—but became famous and respectable through excellent and trenchant reporting for Rolling Stone, particularly on the 2008 financial crisis.
Neither writer was ever a doctrinaire leftist, but it is fair to say that, even when criticizing Democrats and liberals (for example, for continuing the war on terrorism and the use of drones, or for favoring banks over homeowners during the Obama years), their critiques appeared to emerge from positions further left. But over the course of the first Trump term and subsequent Biden presidency, they gradually, then swiftly, drifted into the inchoate, mercurial world of 'heterodox' thinking and writing—a sprawling and capacious complex of pontificators, with tendencies that range from fairly standard Silicon Valley sci-fi libertarianism to fantasy-genre monarchism to hard-right ethnonationalist neofascism.
Both of these main characters became uncomfortable in the liberal media around the time of 'Russiagate,' a sprawling, incomprehensible liberal conspiracy theory that blamed Trump's 2016 victory on Russian state malefactors. Both were deeply skeptical of the theory, while major left-leaning outlets like MSNBC, where Greenwald had once been a greenroom fixture, went particularly big on it. Ironically, however, both Greenwald and Taibbi took an almost conspiratorial view of the media's commitment to Russiagate, treating the dissemination of the theory as a media conspiracy in and of itself, with Taibbi going so far as to compare it (with caveats, to be fair) in scale to the 'WMD affair heading into the Iraq war' rather than as desperate wish-casting by liberals for some explanation, any explanation, for the election of Trump. Both men found friendlier audiences at Fox, where Greenwald became a regular guest of Tucker Carlson, and eventually as far abroad as the hair-sprayed Technicolor studios of Newsmax.
In the years that followed, both men took positions of reflexive hostility to mainstream media and contemporary liberal values. During the pandemic, for example, Taibbi criticized the legacy press for its 'censorship of ivermectin news.' In the Biden years, he grew increasingly critical of any attempts to prosecute Trump for various crimes, arguing, as many conservatives did, that such attempts were inherently politically motivated and would set up cycles of revenge prosecution. Both men evinced growing concern with 'cancel culture': Taibbi created a regular feature on his website called Meet the Censored, in which he interviewed supposedly canceled writers and public figures, and Greenwald lamented that one of his own passion projects, a documentary about the tennis player Martina Navratilova, had been derailed at least in part by the unreasonable objections of trans activists.
These positions brought both men into alignment with a tech elite who increasingly saw value in an unfettered, (mostly) uncensored, alternative online media. Both publish primarily on Substack (Taibbi has over 500,000 subscribers, and Greenwald over 300,000), the newsletter platform that received substantial funding from Marc Andreessen's firm Andreessen Horowitz. Greenwald has also built an impressive audience for his System Update news show on the Thiel-funded, right-wing YouTube alternative, Rumble—a friendly arena for figures with contrarian viewpoints, a maximalist view of free speech, and a reflexive anti-liberalism.
Taibbi, along with Bari Weiss and the reporters Lee Fang and Michael Shellenberger, among others, benefited from a more direct relationship with the tech oligarchy. Shortly after Musk took possession of Twitter in October 2022, he turned over the company's records to these writers, encouraging them to report on the supposedly scandalous practices of the prior regime. Taibbi was first to take up the gauntlet and began to write about the so-called Twitter Files. Rather than initially publishing these revelations as traditional articles in a periodical or newsletter, Taibbi and company struck an unusual deal directly with Musk to report about the billionaire's now-personal platform on that platform, an awkward hybrid format in which the writers revealed and commented on screenshots of internal Twitter company documents in long Twitter threads: disclosing Twitter's internal debates over whether to suppress a New York Post story sourced from Hunter Biden's hacked personal laptop, and showing the company deciding to ban Trump from the platform after January 6. It was a questionable journalistic decision, but it drove a huge number of new subscribers to Taibbi's Substack—at least until Musk got upset about users clicking away from Twitter and throttled outgoing links, to Taibbi's public dismay.Many idiosyncratic figures on the right have long benefited from the largesse of conservative millionaires and billionaires who fund think tanks and institutes and support conservative media from Fox News to The Federalist. But while the ascendant tech industry elite have invested strategically in alternative media and platforms—from Andreesen's early-round support of Substack and Thiel's fundraising for Rumble, to Sacks's podcasting platform, Callin—their direct subsidy of new contrarian media is harder to find. The story of tech in new media is more the tale of investors strategically seeding a friendly ecosystem than it is of rich men simply buying friends and allies. (If anything, the most salient example of a tech billionaire intervening directly in the media was an act of destruction: Thiel's bankrolling of the lawsuit that crushed the left-wing Gawker Media empire.)
In this regard, the title of Higgins's book, Owned, strikes me as a bit of a misnomer. Neither Greenwald nor Taibbi, once beloved and now often despised by the left, seems to have sold out to the tech titans so much as to have converged organically on the same modes of thinking and habits of mind. Greenwald and Taibbi were, after all, already famous and well-off, at least by the standards of a consolidating media industry that mints few superstars and depends more and more on the underpaid labor of freelancers. They had both written for top publications, and both had already benefited from the largesse of a less conservative billionaire, Omidyar, who in addition to funding The Intercept, funded a never-launched Taibbi vehicle called Racket. Both men had legions of adoring readers.
It's possible instead that, in their overtures toward the right, both sought a way to recapture the feeling, the spirit, the frisson of having once been enfants terribles—of reporting on secret documents, as Greenwald did, or partying in Moscow or naming Goldman Sachs a 'great vampire squid,' in Taibbi's case. These were great shots across the bow of the establishment, rude and necessary eructations in a media clubhouse where the biggest newspaper in the country sat on revelatory and necessary stories—exemplified most damningly by The New York Times' decision to hold back blockbuster revelations of massive domestic spying by the NSA at the behest of its contacts in the government. Such opportunities often come only once or twice in a lifetime, in a career, and there is something sad in desperately chasing the high of another hit.
It is also hard to do. As Higgins outlines, Greenwald's two great scoops—the Snowden leaks and the Brazilian Lava Jato scandal—effectively fell into his lap when sources sought him out, and Taibbi was generally more of a commentator than a straight reporter. As their interests and emphases have increasingly turned to the various depredations of speech codes and cancel culture, the opportunities are simply not there. Neither content moderation nor HR departments are—or ever have been—real corporate or political power centers, and no matter how many times Ivy League presidents are hauled before Congress, there is no NSA of woke to be discovered or revealed.
As for Bari Weiss, she, like Taibbi, took a flyer on the Twitter Files, using revelations from the documents to pump subscriptions to her newsletter, which she rebranded from Common Sense to the Free Press and began to build out as something closer to a journal of news and opinion, with a growing stable of contributors. (Notably, according to Higgins's reporting, Musk gave her access at the behest of Andreessen.)
But, Higgins writes, 'unlike Taibbi, Weiss used Musk rather than being used by him and spun the Twitter Files into an independent career move.' She openly broke with Musk when he banned journalists from Twitter for reporting on his personal decision to ban the @ElonJet account, which tracked the movements of his private planes, and in so doing gave herself credibility as an independent voice. Her status has since only grown, and even Greenwald, who had long clashed with Weiss over his admirable consistency on Palestinian rights and her support for Israel, has mostly sought out a rapprochement. While Taibbi and Greenwald have largely remained one-man enterprises, Weiss has built something that looks a good deal more like a traditional media company.The pining for the excitement and relevance of a lost, revolutionary, mythic personal past seems likewise to stalk many of the tech moguls who populate Owned and who appear to long for a media full of pliant mythmakers, what tech investor Balaji Srinivasan calls 'a 'full stack narrative' of tech coverage.' Where at one time they might have stayed up all night coding or devising exit strategies for investments, now a figure like Andreessen is 'an up-all-night group-chatter and Signaler,' corresponding with 'everyone from Nate Silver to the economist Tyler Cowen' and doing online battle with journalistic detractors like Taylor Lorenz.
Once lauded as the new Carnegies of this current great technological and industrial revolution, tech billionaires seem uniquely piqued by criticism of any kind and especially upset not to be considered the heroes and saviors of humanity itself. In that same interview with Ross Douthat, Andreessen recalls with a fondness verging on nostalgia the love affair that Bill Clinton and Al Gore had with big tech, and Barack Obama's infatuation with tech, entrepreneurship, and venture capitalism, until, in Andreessen's telling, sometime in the early 2010s, 'radicalized' young people began showing up in tech companies' employ, their heads full of wild Harvard notions about equality, fairness, diversity, and the problematic rich men who ran the industry they worked for.
There is nothing quite so menacing in this second Trump era as powerful men with a bottomless need for external affirmation.
Tech billionaires' forays into media appear to be driven as much by a need for adulation as by a desire to influence politics. One need only spend a few agonizing minutes scrolling through Musk's cringy, embarrassing X timeline to sense that this is a man who would pay every cent of his $300 billion fortune for just one person to laugh organically at one of his bad jokes.
There is nothing quite so menacing in this second Trump era as powerful men with a bottomless need for external affirmation. Higgins deliberately and explicitly offers no prescription, no pat and upbeat concluding chapter full of chipper solutions. He's right not to. The 'loudest voices' of new media are loud indeed, but the fortunes in the tech world are even vaster and louder, and it is hard to imagine a way to argue or engineer our way beyond them.
If there is to be a way out of this morass of ugly grievance and misdirected rage, then it may simply be that the combination of enormous ambition and desperate need for validation will burn fuel like a rocket and then burn out like one. It is an increasingly common observation that, after more than eight years of crying that Trump is not normal, the resigned attitude of much of the country and the lackadaisical response of Democratic Party leadership to Trump's return suggest that, on the contrary, he and his political tendency have become if not normal then, at least, expected. Perhaps that is a form of hope against hope as well. The loudest voices of contrarian dissent have become what they hate the most: mainstream.