Matt Yglesias and his Substack newsletter are thriving in Biden’s Washington

“So even very small improvements in the welfare of chickens has an incredible sort of aggregate impact,” Yglesias said on a podcast last February, concluding a mini-monologue on poultry with this: “It’s actually very, very important if we can make chickens’ lives slightly better.”

That is a perfect Matt Yglesias quote: grandiose but granular. Draped in idealism and wisdom but anchored in data and incrementalism. Clear on its face but dotted with leaps like “incredible” and “very,” then hedges like “sort of” and “slightly.”

The affect is one of solution, of authority, of “aha!”

The effect is vaporous, curious, “huh?”

When enthusiastic or challenged in conversation, Yglesias’s speaking voice can reach a cartoonish tenor reminiscent of Jiminy Glick. His writing voice, however, remains flat. He is a “logic machine” at the keyboard, according to friends. He is a parody of artificial intelligence, according to haters.

“It’s the best time there’s ever been to be somebody who can write something coherent quickly,” Yglesias says, over coffee. “I find it relaxing to work. I put things out. People yell at me. I will write again the next day.”

Yglesias, 41, has been writing online nonstop since he was 20. In the aughts, he was an insurgent, liberal blogger who helped turn prolific posting into an industry standard. In the 2010s, he co-founded Vox to institutionalize this ethos and to bigfoot old-guard media. Now he’s struck gold on the newsletter platform Substack, where at least 13,000 people each pay Matt Yglesias an average of $80 a year for access to his Yglesiasms, and to a robust comment section about moral relativism and windowless bedrooms and child tax credits and storm-water runoff. On Twitter, Yglesias has more than half a million followers, and a habit of exasperating people with his contrarian stabs at wit. But his Substack is a place where a fractious world is rendered logical, where self-proclaimed moderates and rationalists find refuge from so-called purists and radicals.

There’s an audience for that kind of thing, especially in Washington, especially at a time when the powerful feel rebellious for thinking centrist thoughts.

“I don’t always agree with Matt, but he always makes you think with his unique and sharp insights,” says Ron Klain, the White House chief of staff, via email. Klain has liked and shared multiple Yglesias tweets, usually ones that praise White House actions in defiance of wailing liberals or henpecking conservatives. Yglesias, Klain adds, “offers ‘unconventional wisdom:’ He’s not afraid to break with others and put his views out there — a perspective that is hard to find in a dialogue dominated by conventional wisdom.”

For others — especially those who say Yglesias punches left — his wisdom amounts to sleight of hand.

“I think that Matt is a smart and clever thinker who spends far too much time trying to simplify the world into discrete models, either economic or philosophical, and the world is much messier and much greater digging is required,” says Jeff Hauser of the Revolving Door Project, which saw right through Sam Bankman-Fried, the disgraced cryptocurrency exchange founder whom Yglesias had previously touted.

“He’s basically a panhandler who’s driving outrage on Twitter, and benefits from how he engages with the performance of discourse,” says Melissa Byrne, an activist for student-loan cancellation, which Yglesias dismissed as a political liability for Democrats. (“This was dumb on my part,” he wrote in November, after the party outperformed midterm expectations.)

But enough serious people take Yglesias seriously to negate the many people who don’t. His Substack was tied for most-followed newsletter by members of the Biden transition team, according to digital strategist Rob Blackie, and Yglesias himself was No. 4 on the list of most-followed journalists. Some of Yglesias’s posts on policy — particularly one on Build Back Better negotiations in February — have reportedly circulated among White House staff.

“There’s a broad sense that he’s a public intellectual, and they take his ideas like they’ll take other ideas,” says a White House official who spoke on the condition of anonymity to discuss outside influences on the administration. “He’s not super influential, but he’s a prominent normie liberal, just like Joe Biden is a normie liberal.”

Among the political newsletters on Substack’s leader board, which is stocked with Gen-X reactionaries to what Yglesias has called the “Great Awokening,” he is No. 8 in readership, between the conniptions of Glenn Greenwald and the braying of Andrew Sullivan. Yglesias’s is one of a few Substacks that earn north of $1 million per year in subscription revenue. Yglesias named his Substack “Slow Boring,” after a 1919 lecture by the German sociologist Max Weber titled “Politics as a Vocation,” wherein “boring” is not an adjective of dullness but a gerund of diligence.

“Politics is a strong and slow boring of hard boards,” Weber said at the dawn of the Weimar Republic. “It takes both passion and perspective.”

For two decades, Yglesias has been boring. A million boring posts, across many platforms, into many hard boards — into the brains of like-minded liberals, under the skin of policy experts and the extremely online. He has bored right through the 21st century and emerged exactly where he began: blogging for himself. Except now he’s making bank, and he seems less liberal than he once was.

What changed: Matt, or everything around him?

Two years into his Substack era, Yglesias bores the day away on his MacBook Air in a bare, closet-sized office at a co-working space off 14th Street NW, about 70 feet from a rowhouse where he and his blogger friends spent a portion of their 20s glued to their laptops, posting their way to notoriety amid pizza boxes and poker games. Now he’s entered midlife, like the rest of his Xennial cohort. The hair on his crown has migrated to his eyebrows; his liberal politics have morphed into “reactionary centrism,” according to the internet.

He is mindful, for example, that red-state Democratic senators Jon Tester (Mont.), Joe Manchin III (W.Va.) and Sherrod Brown (Ohio) are up for reelection in 2024 — and that much depends on not alienating their coalitions with far-left slogans and hobby horses.

“The question that I, and other more moderate people, have been trying to get the progressive movement to think about is: How are you going to accomplish anything without those seats?” Yglesias says. “What is the plan to win?”

He’s aged into his curmudgeonliness, though friends say he’s also mellowed. He and his wife, Kate Crawford, have a 7-year-old son. They are Slacking constantly, because Crawford also happens to be his editor and only gatekeeper. She first became aware of him in 2008, when he publicly knocked a congressional candidate she was working for — a Democrat in the South — for not supporting same-sex marriage.

“The candidate was mad that [Matt] had written something that was, frankly, correct, but also a little rude,” Crawford says. Correct but rude: “I feel like that’s Matt in a nutshell.” A Jewish Democrat running for Congress in Alabama had to pick his battles to win and, in 2008, same-sex marriage was not the hill to die on.

“Twenty-seven-year-old Matt was very annoyed by this sort of pragmatism and hypocrisy,” Crawford says. “And I think 40-year-old Matt would be pretty sympathetic to it.”

Yglesias published his first real blog post at 11:50 p.m. on Jan. 10, 2002, while at Harvard.

“Allright … everyone’s talking about this blogger technology — let’s see if it works,” he wrote, before launching into a 198-word commentary on a Slate article about media bias. (Yglesias called it both “on target” and “blah.”)

The blogger technology worked beautifully for him, and he hasn’t stopped posting since: during the balance of the Bush years at The American Prospect, where deep-dive policy analysis found fresh staging on a communal staff blog, and then The Atlantic, where Yglesias’s personal blog attracted 2 million page views in a month; during the peak Obama years at ThinkProgress, a liberal think tank blog that brought him closer to rising Democratic Party leaders; and then at Slate, where he chronicled the economy and lobbed the occasional contrarian softball like “The Case Against Eating Lunch Outside.”

The son of a novelist–screenwriter and a graphic designer at Newsweek, Yglesias comes from a line of passionate writers and dispassionate economists. His maternal grandfather, Jules Joskow, was a Bronx-born pioneer of the economic-consulting industry and a philanthropist for Jewish causes. Matt’s paternal grandfather Jose, born in a cigar-making community in Tampa, clacked his way to the middle class via a pharmaceutical job and a Royal typewriter, penning film criticism for the Communist Party’s Daily Worker, novels about Ybor City and New York, and journalism about Latin America and Martin Luther King Jr. Matt’s paternal grandmother Helen, an editor for The Nation, was later a novelist herself. In the late 1960s the Yglesias household on the Upper West Side hosted a rotating, rambunctious cast of the left-wing intellectual world. The way to make a point was by being louder than the person next to you, recalls Rafael Yglesias, Matt’s father.

“He’s the perfect blend of the two families,” says Rafael, best known for his novel “Fearless,” which he adapted into a 1993 film starring Jeff Bridges. “The Joskow family, in every situation — even looking at a menu in a restaurant — would be able to analyze clearly some flaw in their procedure, some more optimal way they could do something.” On the Yglesias side, Matt “was being given a legacy of ‘‘You say what you believe, no matter what the consequences are.’”

In his last semester at the Dalton School on the Upper East Side, Matt, having secured a spot at Harvard, published a bratty critique of the college application process in the New York Times, in which he mocked the Ivy League administrators who’d admitted him to their rarefied realm. The provocation made him semifamous among classmates before he set foot on campus.

“I remember thinking that, holy s—, this guy is smart — and also that this is a really trivial concept for an article,” says former Harvard classmate Ben Wikler, now chair of the Democratic Party of Wisconsin. At Harvard, Wikler says, Yglesias could “dismember” someone in weekly debates hosted by the Harvard Review of Philosophy. “He could create a 360-degree model of the logic of the argument and find the weak point and blow it up.”

Yglesias majored in philosophy at a time when the idea of America was upended, first by the Sept. 11, 2001, terrorist attacks and then by the fiasco in Iraq, whose invasion Yglesias initially supported. He took a shine to the writings of Willard Van Orman Quine — “a negative philosopher” who was “primarily concerned to criticize others,” according to the Stanford Encyclopedia of Philosophy — and cultivated his own “well, actually” ethic as he entered the world of journalism. Harold Meyerson, editor at large of The American Prospect, recalls a 23-year-old Yglesias being aggressively contrarian in editorial meetings. “I have trouble fitting Matt into an intellectual frame — except skepticism,” Meyerson says. “And skepticism is always necessary as a corrective. But it doesn’t make an ideology.”

Yglesias has always been anchored on the left, even when he tugs toward the center. But a philosophy major’s use of reason, when divorced from nuance and emotion, can curdle into something classist, inhumane, obnoxious. In 2013, at Slate, Yglesias responded to the collapse of a garment factory in Bangladesh by writing that it was “entirely appropriate,” economically, for that nation to have lower safety standards than the United States. Nearly a decade on, some people on Twitter still won’t let him forget that post. Yglesias still defends the core argument while admitting that it was “obviously a bad piece that was poorly timed and poorly framed.”

Benjamin L. McKean, who overlapped with Yglesias at Harvard, used the factory collapse as a touchstone of injustice in his 2020 book “Disorienting Neoliberalism.” He suggests that Yglesias’s misfire on the topic stems from a contrarian impulse. “And I think there’s something similar about supporting the invasion of Iraq,” says McKean, now an Ohio State professor of political science, “which also had unimaginable human costs, through a kind of intellectualizing of why the downsides won’t be such a big deal.”

Put more simply: “I like to provoke,” Yglesias told podcaster Joe Rogan in December 2020, while publicizing his latest provocation, a book titled “One Billion Americans,” which made a nationalist argument for beating China at the population game to maintain American supremacy (an “endearingly crackpot idea,” Jacob Bacharach wrote in his bark-stripping review, “designed for an educated, business-class airport set who have heard of the Aspen Ideas Festival”).

A provocation is a kind of fast boring. But instead of tunneling to a truth, in some cases, Yglesias is hitting a nerve, often needlessly. Hours after the May mass killing at a school in Uvalde, Tex., he tweeted: “For all its very real problems, one shouldn’t lose sight of the fact that the contemporary United States of America is one of the best places to live in all of human history …”

Technically true. But …

“[W]hat the f— man,” New York Times columnist Jamelle Bouie, who also got his start at The American Prospect, replied in a tweet.

“Real people are experiencing actual anguish right now,” tweeted Yglesias’s former Slate colleague Dana Stevens, “and don’t need your middle-of-the-road ‘Well, actually’ garbage.”

In 2020, Yglesias caught blowback for something he didn’t write, but merely co-signed: a letter “on justice and open debate” in Harper’s magazine that decried cancel culture.

Progressive luminaries such as Noam Chomsky, Gloria Steinem and Cornel West also signed their names, bemoaning “the intolerant climate that has set in on all sides,” but so had people with a history of transphobic rhetoric, such as the author J.K. Rowling. In the insane final act of the Trump presidency, in the horrifying first year of the pandemic, after a summer of pain and violence following a policeman’s murder of George Floyd, plenty of people did not want to be scolded by elitists like Matt Yglesias, who had also pushed back on the “defund the police” movement and on young, all-or-nothing climate activists. His signature on the letter triggered a backlash among younger, more liberal staffers at Vox who viewed the letter as a punch-down from the powerful.

“Matt was one of the kindest people at Vox: extremely kind and supportive as a colleague,” says Aja Romano, a culture reporter for Vox. “But it was always sort of difficult to align that with the things he would say online.”

Vox, which Yglesias co-founded in 2014 with The Washington Post’s Melissa Bell and Ezra Klein, was an attempt to forge the Yglesian model of policy analysis into a media kingdom. The experiment failed in that respect, Yglesias says. “We thought we had ideas around explainers and different ways of thinking about journalism that could genuinely disrupt and dominate, changing the way journalism works,” he wrote last month on his Substack. “That didn’t happen.”

Shortly after the Harper’s letter, Yglesias decamped to Substack. He saw a financially feasible opportunity to return to his blogging roots, unfettered by the guardrails of a media institution or the “woke” culture of its newest disrupters.

“He didn’t seem to be able to be his true self at Vox,” says Substack co-founder Hamish McKenzie, who helped to recruit Yglesias. “It seemed obvious to me that Substack would be good for him, not only financially,” but also “for his soul.”

Rather than trying to change the media landscape, Yglesias is back to tending his own garden. His audience is relatively small (by internet standards) but highly invested (by internet standards). And in Biden’s Washington, his old friends, acquaintances and sources are now in positions of power.

“People who were unimportant when Obama was president are more important now,” Yglesias says. “A whole generation of pundits has sort of faded from the scene. And, you know, others have risen in their place.”

People grow up, in other words. A person’s principles parallax with the priorities of the Left, or of society at large. Coalitions fracture and realign. The Overton Window keeps shifting. The insurgents of yesteryear attain status, and maybe a status quo.

“Matt’s just a very contrary person, but I think he has a lot of integrity, which has been a core element of his personality since college,” says journalist Timothy B. Lee, who worked at Vox and has known Yglesias for nearly 20 years. “And so, in the 2000s, that meant being more liberal than most pundits. Now it’s the opposite. But he has the same approach.”

Like Washington columnists of yore, Yglesias is in a rolling, off-the-record conversation with many major and minor players in politics: academics, executives, pollsters, strategists, Hill staffers, members of Congress, fellow panelists at conferences and fellow travelers on international junkets — people from whom Yglesias wants to learn, who want to pull him this way or that, or who want to vent what they can’t say in public but hope Matt will say for them.

“When I talk to members of Congress or people in the administration,” Yglesias says, “I feel like they’re, like, talking to their therapist about their frustrations with intra-coalitional dynamics.”

In September the treasury secretary called Yglesias to chat. Why? Janet L. Yellen’s communications staff did not respond to inquiries about why. But Yglesias then wrote a post extolling “modern supply-side economics” and concluding that, when it comes to the wobbly economy, the Biden administration seems “to be going in the right direction.”

Is this wisdom? If so, is it conventional or unconventional?

Perhaps it’s instructive to think about two topics that bookend his public life. At age 21, Yglesias was laying out the logician’s case for the invasion of Iraq, because how could the most powerful, informed men on Earth be so stupid? In May of this year, Yglesias declared that Bankman-Fried “is for real,” because why else would wealthy people risk their money?

“Unfortunately I think, like most people, I just kind of took it at face value,” Yglesias says now, about Bankman-Fried’s endeavor. “‘Well, if his company has a $20-billion valuation, there must be something to it.’ Even if I don’t understand what a cryptocurrency exchange is.”

This is Matt Yglesias coddling the powerful, his critics would say, and exposing a gullible dilettantism. And yet plenty of people view him as an early, sensible and stalwart voice for incremental progress on key issues of the 21st century, such as marijuana reform and same-sex marriage.

“He’s got a pretty pragmatic view of” criminal justice reform and “defund the police,” says Texas Southern University professor Howard Henderson, an expert on culturally responsive criminal justice research. Sometimes the “voice of reason doesn’t necessarily come from the community, or from the criminal justice activists, or the police themselves. … Sometimes you need people like Matt to actually throw out these ideas in a manner that’s approachable and debatable.”

“I think Matt has had a huge, singular effect on the housing debate, in ways that are harder to see now because his views are so widely shared,” says Klein, a longtime friend, referring to Yglesias’s decades-long promotion of YIMBYism to confront the nation’s housing crisis. “My most significant disagreement with Matt, typically, is that I think the world is less logical than he is, and so arguments that are extremely convincing and internally very tight often don’t track the frustratingly messy ways that people and institutions work.”

Blowback to many of Yglesias’s opinions is “rooted in Matt being of D.C., and really understanding the place, and a lot of people who just don’t get it wishing it were different,” says Matthew Lewis, a liberal activist who’s worked in spaces that Yglesias has long written about, such as housing and climate. “Look, the Senate is a place that exists.”

And Matt Yglesias is a person who exists in this world, with all its intellectual absolutism and strategic compromise. It’s a world where progress happens through, well, a slow boring of hard boards.

“People often talk to me because they want to draw more attention to some kind of internal disagreement” on the hard boards of policy and politics, Yglesias says. “And the only way for me to do that is for them to explain to me what’s going on. And, you know, sometimes it can be a process.”

He offers an example having to do with carbon sequestration, and who’s advocating what, and why, as the Earth burns up. Sometimes, to grasp a complex and spiraling world, it helps to fixate on something so specific that it will make your eyes glaze over.

“I’ve been learning lately,” he says, “about something called Class VI wells.”

What are Class VI wells? Matt Yglesias can tell you. He will sound like he knows what he’s talking about. And it’ll be one big bore.