BARI Weiss was at home in Larchmont Village, changing her three-month-old’s diapers, when she heard her cell phone ping. It was a text message from the richest man in the history of the world.
“He asked if I wanted to go to Twitter headquarters in San Francisco and look at the Twitter archive,” she says about Elon Musk’s message. “It was a Friday evening, around six p.m., but I was like, ‘Sure, why not,’ and ran to pack my bags. I was on an 8 p.m. flight. I was at Twitter HQ by 11 p.m. I mean, I’m a journalist, why wouldn’t I go?”
When she arrived, Musk was there to greet her, along with a few of his bodyguards, a couple of engineers, and one of his eight children, two-year-old X, who zoomed around the otherwise empty, mostly darkened Twitter offices as the billionaire laid out his ground rules for looking at the archives in a windowless, under-ventilated conference room on the tenth floor. They were the same terms he’d presented to a handful of other journalists, like former Rolling Stone columnist Matt Taibbi, and they were as simple as they were seductive.
Musk would grant Weiss and her team unfettered access to Old Twitter’s internal memos and private emails regarding its content-moderation policies before he purchased the company earlier this year, policies that had been criticized by conservatives for allegedly silencing their voices and promoting the so-called liberal-woke agenda. Weiss could plug in any search term she wanted and could write whatever she wanted about whatever she found in the archive. But she’d be required to publish it first on Twitter, in a series of 280-character tweets.
“My reaction was, ‘I can’t wait to dig into the documents,’” she says.
And so it was, during the last chilly weeks of 2022, that Bari Weiss, the 38-year-old former New York Times op-ed writer-turned-Substack superstar, the Jewish lesbian from Pittsburgh who liberals (and some conservatives) love to loathe, got sucked into the Twitter Files—you know, the buzzy series of exposés-in-tweets that first Taibbi and then Weiss and other journalists started posting in early December and are either the most important scoop since Woodward and Bernstein covered Watergate or else a big fat nothingburger, barely worthy of a yawn.
Like most of the controversies swirling around Weiss, where you stand depends on your political point of view.
Of course, this is hardly the first time Weiss has found herself smack in the middle of a media mega-storm. Indeed, her entire career has been one gale-force squall after another, starting as far back as her student-activist days as an undergraduate at Columbia University in the mid-2000s, where she first made a name for herself protesting against professors in the Middle East studies department that she and other Jewish students accused of anti-Semitism. Even now, her critics charge that Weiss, who frequently rails against “cancel culture” lobbied to get one professor fired, an accusation that she firmly denies.
Years later, during the Trump era, Weiss had become one of the country’s most talked about—or shouted-about—opinion writers, particularly in progressive circles. Her dramatic public resignation from the New York Times in 2020 dropped like an A-bomb on the media establishment. Some people—well, her grandmother—still haven’t gotten over it.
Somehow, though, this latest brouhaha over the Twitter Files feels a little different—and yet also entirely familiar. A self-professed centrist, Weiss once again finds herself dangling in the middle, a perennial political piñata, with just about everyone taking a whack at her.
Progressives are denouncing her as an opportunistic culture warrior stoking old grievances over Twitter as a way to boost her own brand—a brand, by the way, that now includes a spanking-new website and media company, the Free Press, which Weiss launched in the middle of the uproar. (More on that later.) Meanwhile, the conservatives who initially cheered her Twitter Files reporting, seeing it as smoking-gun proof that the site had indeed been throttling their accounts, began turning on Weiss the minute her dealings with Musk went south. Which they inevitably did, as Musk continued his startling transformation into the Joker, flinging open Twitter’s doors to Q-Anon crazies and neo-Nazis and—the last straw for Weiss—banishing several prominent journalists from Twitter for reporting on the fact that Musk had earlier banned an account that had been keeping track of his private jet’s whereabouts.
“The old regime at Twitter governed by its own whims and biases and it sure looks like the new regime has the same problem,” Weiss tweeted about the private-jet controversy, starting a brawl with the tech magnate who’d just a few weeks earlier invited her to rummage through his archives. “I oppose it in both cases. And I think those journalists who were reporting on a story of public importance should be reinstated.”
“Rather than rigorously pursuing truth, you are virtue-signaling to show that you are ‘good’ in the eyes of the media elite,” Musk instantly tweeted back at Weiss, clearly unaware that Weiss has never been considered remotely “good” by the media elite and probably never will be. Then, in the ultimate act of spiteful vengeance—at least for a social-media mogul—Musk stopped following her and The Free Press.
“It’s been exhausting,” Weiss says with a sigh. “It’s like the classic Jewish position—like I’ll never be a part of any of these tribes. But, listen, all I can do is stick to my principles. That’s all I can do. Let the chips fall where they may.”
If Weiss truly is what her detractors claim—pure evil, the Lord Voldemort of the chattering class—she’s pretty good at disguising it, at least in person. When you meet her in the flesh, she is nothing like the finger-tenting supervillain her enemies describe.
For one thing, she’s a hugger, even with strangers bearing tape recorders who come to interview her at her home, a tasteful, casually decorated, sprawling bungalow where she’s been holed up with wife Nellie Bowles, a former Times tech reporter, since leaving New York in 2020. In fact, she’s so fizzy and upbeat, there really is only one word that fits her, and that word, which she’d hate, is “bubbly.” But Weiss is also super sharp and hyper-articulate. She’s got the coolly casual confidence of someone accustomed to being the smartest kid in the class but who has learned, over the years, not to be obnoxious about it.
In other words, she’s less Voldemort, more Hermione Granger, if Hermione had been a nice Jewish girl from Pennsylvania.
And yet, for some reason, Weiss is also insanely triggering to a lot of folks, mostly liberals. “The real defining feature of Bari Weiss is how absolutely, categorically stupid she is,” reads one typically nasty tweet from Tom Scocca, a writer who’s made a hobby out of regularly trolling Weiss online. And the hate isn’t just happening on the internet. Before the story you’re reading now was published—before it was written—its author received irate phone calls from progressive friends and colleagues who were furious that Weiss was being given a “platform” in the pages of Los Angeles magazine. One caller hung up in a flurry of obscenities. (Interestingly, though, not one of the Never-Weisses Los Angeles reached out to agreed to be interviewed for this piece).
But crack open the Weiss Files—her writings back when she was at the Times, as well as her pieces for Commentary and her own Substack, Common Sense—and it’s hard to figure out what’s got everyone so unhinged. She’s pro-choice, pro-gun control, pro-Democracy (meaning anti-Trump), and pro-LBGTQ rights. True, she’s also pro-Israel, a position shared by a majority of Americans that’s become increasingly incendiary in academia and the media. She also defended Brett Kavanaugh—sort of—during his Supreme Court confirmation hearing, arguing that it wasn’t his behavior in high school that disqualified him, but his behavior in front of the Judiciary Committee, and has frequently pushed back against cancel culture in media and on college campuses.
Still, it’s puzzling. Bill Maher can be as heterodoxic as he likes on his HBO show and he doesn’t stir up nearly the furor that Weiss does. Joe Rogan can denounce woke culture to his heart’s content on his podcast and won’t set off this sort of red-hot rage. But if Bari Weiss suggests in a column—not unreasonably, perhaps—that shutting down schools for nearly two years during the pandemic possibly wasn’t such a hot idea, after all, it sets off such fury you’d think she’d incited an insurrection.
“I don’t get the rage,” says writer Andrew Sullivan, who’s stirred up quite a bit of it himself with his centrist musings in New York magazine (until he was pushed out and started his own Substack). “Maybe it’s because a young Jewish lesbian is not allowed to violate the orthodoxy and tribal identities that are now so hard-wired they have no relationship to objective reality. I think also they know she understands the social-justice left and how it operates, so she is dangerous and cannot be intimidated. Then there’s her defense of Israel.”
Weiss herself throws up her hands when asked about it.
“There are two things I’ve given up on,” she says, settling into a chair in a backyard shack that she’s turned into a soundproofed podcasting studio. “One is trying to figure out why I trigger people the way I do. And the second is trying to resist it when people mislabel me in some way. Because it’s maddening when you trend on Twitter as a caricature of yourself, as something totally unrecognizable to you. It’s really upsetting and disorienting. I don’t think human beings are meant to withstand that kind of incoming. I’m definitely not.”
There certainly aren’t many hints in her history as to how antagonizing liberals became one of Weiss’s superpowers. She’s always been very much a middle-of-the-road sort of gal. In fact, she literally grew up in Mr. Rogers’s neighborhood.
Her parents were in the flooring business in Squirrel Hill, the Pittsburgh suburb where Fred Rogers lived—and where, years later, in 2018, an anti-Semite shot up the Tree of Life synagogue, the temple where Weiss had been bat mitzvah’d. (She wrote movingly about the tragedy in a Times column titled “When a Terrorist Comes to Your Hometown.”)
“I was a Type-A kid,” she says, unsurprisingly. “I was kind of a theater nerd, loved musicals, loved watching the Oscars, but I also read a lot. I was reading The New Republic when I was 12 years old. It was really great back then. Michael Kinsley was editor.”
After high school, she spent a year in Israel, working in a kibbutz kitchen. Then she headed to Columbia, where she started out dabbling in theater and dated a classmate named Kate McKinnon. “We met in a play that I did my freshman year,” is about all she’ll say about her youthful love affair with the future SNL star, other than, “It was a very formative relationship, in many ways.”
Columbia in the mid-2000s was a hotbed of student activism, so Weiss fit right in. She helped form Columbians for Academic Freedom, a student group that made national news when it accused pro-Palestinian professors of anti-Semitic polemics (the group’s critics claimed Weiss and the others were trying to get faculty fired for their opinions). For the first time, Weiss started taking writing seriously, penning think pieces for the student newspaper, The Daily Spectator. “I always liked getting into political arguments, but I found it was way more exciting to do it on the page,” she says.
Her first gig out of school was an internship at the Wall Street Journal. She ended up sticking around for a staff job, writing opinion pieces and editing book reviews. “It was a very male environment, and I was more liberal than most of the people there,” she recalls. “And I was young. I didn’t have strong feelings about stuff like the child income tax credit, which really animated people there. For years, I wondered if there was something wrong with me because I couldn’t get it up for those sorts of subjects.”
It was around this time that Weiss, who considers herself bisexual, got married for the first time, to an environmental engineer. The marriage lasted only a couple of years, but there were apparently no hard feelings. “A total mensch,” is how she describes him today.
Then, in 2016, Weiss, along with WSJ’s Bret Stephens, got offers to join the editorial staff at the New York Times, which had been caught flat-footed by the election of Donald Trump. “We were ideological diversity hires,” she says, laughing. “There was a lot of soul searching at the Times after Trump’s election, and there was an effort to bring in more people with different sensibilities.”
She had a different sensibility, alright. Suddenly, she went from being the most liberal writer at the Journal to being the most conservative at the Times. Still, her family was thrilled. “When I told my grandparents that I was working at the New York Times, I think it was the happiest moment of their lives,” she says. “They’re the prototypical Times readers. My grandma still doesn’t understand why I left.”
For Grandma, then, here are the reasons. From the start, Weiss says, her colleagues reacted to her hiring as if the love child of Roger Stone and Stephen Miller had taken up residence in the cubicle next to them. Weiss suspects, however, that it wasn’t merely her middle-of-the-road politics that offended her new coworkers. “If you googled me at that point, the things you would see about me were: Jewish, Zionist, feminist, bisexual, gay, and Pittsburgh,” she says. “What is it among those descriptions that might be unpopular?” She waits a beat for an answer before giving one. “At institutions like the New York Times, ‘Zionist’ is a dirty word.”
It only got worse over time, as Weiss penned columns that many of her coworkers considered ideological apostasy. Her piece on the Women’s March, for instance, in which she flagged the anti-Semitic histories of some of the event’s organizers, didn’t win her any popularity contests on the staff. Another column defending Parks and Recreation star Aziz Ansari from what turned out to be dubious accusations of sexual assault —“Aziz Ansari is Guilty. Of Not Being a Mind Reader”—also went over like a lead balloon with her colleagues, although it did win her one notable fan. After Bill Maher saw the piece, he invited Weiss onto his show.
“I read that column and said, ‘I’m going to make her famous,’” Maher recalls. “And I did. I had her on the show three times that first year and I asked the same questions you’re asking. Why is this lesbian Jewish girl now considered conservative? It wasn’t many years ago that people like Bari and I were considered down-the-middle liberals. We’re still fairly left of center. It’s not like we’re against gay marriage or anything. I mean, Bari is in one. But we live in an era of extremes, and in a lot of people’s minds, you’re either all in or you’re not.”
Weiss’s Real Time appearances were followed up by a glossy Vanity Fair profile in which she was photographed sashaying down a wind-swept New York City street in a red Valentino dress and Manolo Blahnik heels, looking like she’d just joined the cast of Sex and the City. That didn’t help matters back at the office either.
“Bari was treated terribly by her coworkers the entire time she worked there, but I never thought it was because of her politics,” says Shawn McCreesh, a New York magazine writer who at that time worked at the Times as Maureen Dowd’s assistant. “If you go back and look at the stuff she was writing, none of it was that controversial. She was just writing what every sane person thought but didn’t have the balls to say. But that made her a star. Suddenly she was on Bill Maher every other week and being photographed by Vanity Fair. And that drove the staff—all these group-thinkers who were toiling away on their pious opinion pieces—nuts. You cannot overstate how jealous and petty people who work in the media are. So it just got nastier as time went on.”
Weiss did manage to make a few pals at the Times. While other colleagues were bad-mouthing her in the newsroom, or openly crapping on her on the paper’s internal Slack channels, she also struck up a long-distance texting relationship with Bowles, then still at the Times, who happens to be a member of a prominent San Francisco family. (She’s a descendant of nineteenth-century cattle baron Henry Miller, once the largest landowner in the U.S.) “Bari really needed a friend,” Bowles says with a chuckle after she joins Weiss in the podcast shack. Their friendship turned romantic shortly after she and Weiss met for a drink in the West Village when Bowles was in town for a story. That also didn’t go over well at the office.
“A group of us were standing around having drinks in one of the bureaus,” Bowles recalls, “and an editor turned to me and in front of other people said, ‘You’re dating a Nazi. She’s a fucking Nazi!’ I tried to laugh because it was so uncomfortable and intense and aggressive. But it just got worse from there.”
Eventually, Weiss couldn’t take it anymore. In July 2020, she resigned in the most public way imaginable. In an open letter to Times publisher A.G. Sulzberger, Weiss laid out her grievances for all the world to see, from her colleagues’ bullying online (“Some coworkers insist I need to be rooted out if this company is to be a truly ‘inclusive’ one, while others post ax emojis next to my name”) to what she saw as the paper’s embrace of progressive small-mindedness and a narrowing of its ideological tolerance. “Twitter is not on the masthead of the New York Times,” she wrote. “But Twitter has become its ultimate editor.”
Not surprisingly, the letter made a huge splash in New York media circles. Some of Weiss’s critics believe that was the point—they’re convinced her “self-canceling” was all part of a plot to draw attention to herself. Others dismissed her complaints in the open letter as whining. “She is literally asking the Times to prevent people at the paper from criticizing her, on the grounds that she dislikes the criticism,” wrote Noah Berlatsky in the Observer. A former Times Executive Editor, Jill Abramson, was even tougher on Weiss. “[She’s been] on Twitter throwing some punches herself,” she said at the time, “but if you are going to dish it out, you’ve got to be ready to take it.”
Still, there were some who quietly cheered Weiss’s audacity. “What was she supposed to do—slink out of there?” asks McCreesh. “After putting up with shit for years, she went out swinging.”
According to Weiss, though, her quitting was a spontaneous act of desperation. “There was zero plan,” she insists. “Nothing.” In fact, Weiss caught herself so off-guard with the decision to leave the Times, she found herself without health insurance. “And then Nellie, who was still at the paper, suggested we go get an instant marriage, so I could get on her insurance. We were already engaged, so that’s what we did.”
“After that, Bari was just wandering around unemployed, sitting around the house,” Bowles says. “She was like, ‘Should I become a rabbi?’”
Eventually, Bowles managed to coax Weiss out of her one-bedroom walkup apartment—and out of New York altogether. The couple headed west and resettled in Los Angeles. “Nellie is a sixth-generation Californian,” Weiss says. “She’s from San Francisco, and if she had her druthers, we would probably be living there. But I needed to be in a place that had energy, so I picked L.A., and I’ve found it to be an unbelievably rich environment for making friends and meeting people that are building incredible things. Sure, there are more people with plastic surgery walking around than there were on the Upper West Side, but it’s the only place we could be.”
Weiss and Bowles (who converted to Judaism since meeting Weiss) have indeed made new friends here, attracting a coterie of ex-pats from the old left and other assorted political and cultural oddballs. Weiss recently threw a party at Fia in Santa Monica to celebrate the publication of British author Douglas Murray’s latest tome, The War on the West: How to Prevail in the Age of Unreason. The guest list included renowned playwright-turned-nutty right-winger David Mamet, former Love Line host-turned-cranky podcaster Adam Carolla, and Brian Grazer’s ex-wife, conservative novelist Gigi Levangie. Weiss has also scored an agent at CAA, guest-hosted on The View, and—the ultimate expression of acceptance in this town—was even mentioned in an episode of Curb Your Enthusiasm. (Larry slams a door when he hears her name.)
Sure enough, it wasn’t long before inspiration struck, and Weiss found a new calling—although the idea came not while she was in California but at 30,000 feet on a flight to Miami. Also, it wasn’t her idea.
Bowles says, “I opened a computer, noodled around with the airplane Wi-Fi, and I started a Substack for Bari, which I knew about from being a tech reporter.” That was the day in January 2021 when Common Sense came into being. “And I told her, ‘Here, you’re starting this.’ And Bari was like, ‘No, I don’t want to do a newsletter. It looks weak.’ And I was like, ‘No, it’s going to be great.’”
Bowles was right, it was great. Within a year, Weiss’s new Substack, which she named after Thomas Paine’s famous pamphlet, was generating more than $800,000 annually from 14,000 paid subscribers, with another 75,000 in nonpaying followers. “I’ve made a lot more money than I ever thought was possible in journalism,” she told CNN Business in October 2021. Within another year, Weiss was raking in even more bucks, with Common Sense swelling to some 280,000 paid and free subscribers and a spin-off podcast, Honestly with Bari Weiss, drawing thousands more listeners to her conversations with everyone from Bibi Netanyahu to Kim Kardashian.
By November 2021, Weiss was even announcing the formation of a new college to help fix America’s “broken” higher education system—University of Austin — although that endeavor still remains largely theoretical, with only a couple of summer classes held so far. (“The Twitterati have compared the University of Austin to Trump University,” quipped a speaker at a recent Commentary magazine roast for Weiss. “That’s not fair. A semester at Trump University lasted more than two weeks.”)
But then, she and Bowles—who by then had also resigned from the Times— hit on an even bigger idea. They decided to start their own media company. “We’re going to pick up the flag that legacy news organizations have put down,” Weiss says, explaining the master plan behind The Free Press. “If you’re someone that used to read the New York Times and listen to NPR in the morning, and now you’re thinking to yourself, ‘I don’t know if I can trust what I hear or read there anymore,’ where do you go? Those people want a publication that will treat them like adults, with respect and transparency, and honesty. And that’s what we’re going to try to do with the Free Press.”
“Welcome to the kibbutz,” Weiss says in early December, waving a hand towards a group of young reporters huddled around a kitchen island tapping on laptops. A few others are lounging on easy chairs in her living room, dangling their legs over armrests, also typing into MacBooks. A couple of yapping dogs dash from room to room. Later, Weiss’s and Bowles’s three-month-old baby girl will make a brief, loud appearance.
This is headquarters for the Free Press, or at least it will be when the brand-new media company—not just a newsletter anymore but a website with an actual full-time staff, more podcasts, and eventually books and live events—launches in another 24 hours or so. Originally, they had a bit more time to prepare—D-Day was scheduled for mid-December—but then a certain richest man in history texted her with the Twitter Files invite and that moved the timetable up a week: After all, what better way to advertise and promote a new media venture than with the biggest media scoop of the century. Or even with a nothingburger, so long as it makes enough noise.
The point being, Weiss’s timing couldn’t have been more impeccable. Within a day or two of posting her Twitter File thread, her followers more than doubled to nearly a million. Some of those clicks must have spilled over into her Free Press traffic because within a week of launching, it was already up to 300,000 subscribers. Weiss is cagey about revealing how many of those subscriptions are paid versus free—and clearly, a huge chunk of them were old Common Sense subscribers who’d been rolled over to the Free Press, where Weiss’s Common Sense writings will now be a column. But even if it’s just 20 percent paying the $7 a month fee, that’s more than $5 million in annual revenue. Together with a small “friends and family” loan that Weiss says helped bankroll the startup—along with a reported investment by venture capitalist and mainstream media hater Marc Andreesen—that should be plenty to keep the presses rolling for at least a while.
For now, Weiss’s kitchen—er, newsroom—remains a bootstrap operation, with just a dozen full-time staffers. But it’s an eclectic crew, ranging from a 67-year-old former Slate scribe to a 27-year-old former New York Post writer (that’d be Weiss’s little sister, Suzy) to 38-year-old Andy Mills, one of the creators of the New York Times podcast The Daily. The Free Press is presenting itself as an island of calm, centrist sanity in an ocean of ideological extremism, so it’s not surprising that it tends to attract writers and editors who sound a little fed up with media as usual in the twenty-first century.
“We are tapping into something that I think many, many Americans crave,” says one of her new hires, Peter Savodnik, a former Vanity Fair writer, “which is a thoughtful conversation about the issues of the day where you don’t have to be afraid of using the wrong word, where you’re allowed to disagree with people without hating them.”
“I don’t know where my coworkers are politically,” agrees Emily Yoffe, the veteran former Slate writer, “but we’re all on the same page about being able to have a robust conversation, about publishing things that not all of us necessarily agree with. That used to be what good journalism was all about—being provocative, telling the reader something they didn’t know. That’s not so much the case anymore. And that’s a shame.”
Thanks to her short-lived adventure with Musk, Weiss is now used to writing in tweet-sized bits, so she puts it all the more succinctly. “The Free Press is for the vast majority of Americans who aren’t on the hard left and aren’t on the hard right,” she says of her latest journey down that treacherous, narrow lane known as the middle of the road. “It’s telling those people that they’re not crazy and they’re not alone.”
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