“We’re like the Fyre Festival of media,” an ex-reporter from the Messenger tells me. It had been one week since his employer had shut down the news Web site in spectacular, shocking fashion—deleting all the site’s articles, deactivating employee badges and Slack channels, and refusing to pay severance. The parallels to the doomed music festival—not to mention Quibi, New Coke, and the Titanic—are real.
The Messenger was the brainchild—if we can be so kind—of publisher Jimmy Finkelstein, who managed to raise $50 million from investors for a start-up idea straight out of 2013: a something-for-everyone Web site that would stay studiously nonpartisan and turn a profit through old-fashioned ad sales. The Web site’s launch was one of the biggest media stories of 2023, both for its ambition—building a national news brand from scratch—and its arrogance.
There is now a class-action lawsuit against the company; a surfeit of what-went-wrong stories; and a rumored documentary. But out of the epic failure has come something inspirational as well: a cathartic and nurturing online community.
“It was clear that we were going under” on January 31, former deputy business-and-finance editor Dawn Kopecki says. So Kopecki created a shared Google document to collect personal contact info for staffers and posted the link in the corporate Slack.
Kopecki acted just in time. “Our work Slack got cut off as we were all saying, ‘What are we all going to do?’” an ex-writer tells me. She “felt helpless” and was going to “sulk by myself.”
But Neil Paine, the site’s senior editor for sports data and innovation, had been through this before, having been laid off from FiveThirtyEight when Disney “streamlined” that brand the previous April, and he found it helpful to keep in touch with former colleagues through a personal Slack. “Having Slack was a way to maintain normalcy,” he says, since he had worked from home and lived on the platform.
That’s why Paine created the Slack channel Ex-Messengers. He says he wanted to “give people a place to network and talk about job opportunities.” Journalists being journalists, it also became a venue for commiserating and score-settling.
Kopecki’s Google document helped the group grow quickly; nearly all of the start-up’s 300 former employees have joined. “People are bending over backwards to help each other out,” an ex-staffer says, by sharing job leads and tips about health insurance. Finkelstein is not invited.
There is now a lawsuit against the company; a surfeit of what-went-wrong stories; and a rumored documentary.
A lawsuit alleging that the Messenger had violated the Worker Adjustment and Retraining Notification (WARN) law was hatched in part in the Slack group, staffers say. The group was also used to organize a GoFundMe page for staffers who were living paycheck to paycheck.
“It’s provided a real refuge for people,” Kopecki says. “We’re all in this together.”
One Slack channel has been dedicated to the hellish process of filing for unemployment insurance. Another, named Receipts, has filled up with tales of dysfunction and reckless spending. A third was simply named Jimmy.
“There was no reason for it to exist,” a friend of Finkelstein’s admits. But Finkelstein talked a big game, telling The New York Times that he really wanted to “do something that changes journalism a bit and changes America for the good.”
Some of his initial hires believed him. Others just needed a job. Of the 32 Ex-Messengers I interviewed for this article (most of whom requested anonymity because they need new jobs now), about half said a version of “None of us thought this was going to work.”
“But,” as one ex-editor says, “we thought it would last at least a year.” Several recounted being told by Finkelstein that the start-up had three to four years of runway, meaning sufficient financing and a stable business plan. Some recruits signed long-term contracts at above-market rates. “It all seemed very glamorous to me,” one ex-reporter says, “but it also seemed like a huge waste of money.”
Finkelstein did not respond to my requests for an interview. When I sent him a list of fact-checking questions, he called a few minutes later and said that everything I was planning to report was wrong. He said any comparison to the Fyre Festival was offensive because that was a fraud, while the Messenger was a fast-growing start-up with star reporters. So what went wrong? I asked him. Why did the money dry up so soon? What about the staffers with long-term contracts? Finkelstein said he was declining my interview, and that was that.
“A New Kind of News”?
Finkelstein, previously an owner of The Hill, which he inherited from his father, Jerry, and The Hollywood Reporter, had delusions of publishing grandeur. “The day I saw the New York office for the first time,” another ex-reporter says, “with its rows of empty desks and sweeping high-floor views—I knew we were cooked.”
There were opulent, enormous offices in Washington, Los Angeles, and West Palm Beach, too. “It was like Jimmy was living in a world where the pandemic never happened,” an ex-writer remarked.
The site launched in mid-May with a tagline that promised “a new kind of news.” Instead, it was mostly an old form of aggregation. Finkelstein’s plan—outdated, in the minds of many of his own staffers—was predicated on generating huge amounts of traffic, which meant stupendous amounts of clickbait. “I’m actually relieved they erased our clips, because I’m so embarrassed by them,” an ex-reporter tells me. “My byline was on so much garbage.”
This is one of the reasons why the Ex-Messengers group has been so rewarding for the participants. “Editors in the Slack chat keep apologizing for assigning shitty stories, saying, ‘I’m so sorry. I didn’t want to do this, either,’” the ex-reporter adds.
When the Messenger was still alive, there wasn’t a robust newsroom culture, to say the least. Staffers barely got to know each other. “We were too busy shoveling coal into the furnaces, trying to keep the power on,” one editor says. Writers in, say, the business section barely even knew there was a sports section or a lifestyle vertical. “We begged for a staff directory and never received one,” the editor says.
Overlap was a big problem. Different sections routinely rushed to write about the same clickable topics, so the site sometimes published two versions of the same story. Editors lacked the workflow and collaboration tools that might have helped avoid such situations. “Jimmy raised $50 million, and he told us to plan on a fucking Google doc,” an ex-editor gripes.
In my conversations, I heard over and over again about broken promises and inflated predictions. The Messenger’s management team projected 100 million monthly readers and more than $100 million in revenue, but fell so laughably short that ex-staffers now feel the joke was on them.
Finkelstein had plenty of his own grievances, according to staffers who were on the receiving end of his calls and messages. His purported desire for an unbiased news product was undercut by his penchant for Donald Trump. He complained about what he called “anti-Trump stories” even when the stories merely reported on the former president’s legal woes. (Finkelstein told me, “I wanted to protect the brand, to make sure that it was neutral,” but “the editors always had the final say.”)
“I’m actually relieved they erased our clips, because I’m so embarrassed by them. My byline was on so much garbage.”
“[Finkelstein] was spending his time fuming and sort of tone-policing what headlines would say, what the mix was on the home page,” ex-reporter Marc Caputo said on a podcast last week. “You’re a businessman. Focus on the fucking business” is how he paraphrased his reaction.
In the Ex-Messengers group, people from disparate sections, all the way from politics to wellness, have learned that they felt the same pressures from management.
Jimmy once called the opinion team into a last-minute meeting in December,” ex-editor Christine Ayala recalled in a Slack post. Ayala thought Finkelstein was announcing layoffs. Instead, he joined the Zoom call “from his literal bed, telling us he was sick—but wanted to talk to us about how everything we posted was boring and not good,” Ayala wrote. “He had the comforter up to his chest and everything, like he just woke up from a fever dream.”
By then, the start-up was in dire financial straits. Finkelstein sought a lifeline by meeting with a group of right-wing businessmen at Mar-a-Lago on January 3, the same day he conducted a limited round of layoffs in an apparent bid to stretch the Messenger’s existing funding a little bit longer. According to one of Finkelstein’s confidants, management conducted a “byline count and click count” and “got rid of the people who didn’t score well.”
The cuts spooked the remaining staffers, notwithstanding a statement promising that the company was “not planning any further layoffs.” Finkelstein, meanwhile, continued to exude confidence. While talking with associates at the funeral for Melania Trump’s mother, Amalija Knavs, in Palm Beach in January, “he said all was well,” according to one insider. “He insisted he would get the funding.”
Finkelstein’s “don’t worry” attitude worried the instinctively skeptical reporters on his staff, many of whom spent the month of January asking, sometimes explicitly, “How are we going to survive?” Others retreated inward. After I was interviewed by a Messenger reporter in early January (for a story that never ran), I alluded to the site’s shaky future, and the reporter said she was trying to tune it all out.
“Each department was its own city-state,” another ex-editor says. Tanita A. Gaither, who was the Messenger’s managing editor of audience, referred to this disconnect when she replied to ex-editor Dan Wakeford’s January LinkedIn post praising the start-up’s “best in class” journalists, writing that a conversation she’d had with him earlier that month “was the first time I ever heard you speak and I’d been working there since July. And I didn’t even know you were British.”
Gaither’s comment was deleted, presumably by Wakeford, but a screengrab of her post was savored in the new Slack channel, where ex-staffers were aghast at published reports that Wakeford’s annual salary was $900,000. Numerous staffers described Wakeford, the former editor of People and In Touch Weekly, as charming but out of his depth and often AWOL. Ex-employees said Wakeford was hemmed in by Finkelstein and told to limit his interactions with rank-and-file newsroom staffers, much to his chagrin. Wakeford did not respond to Air mail’s request for comment.
Staffers barely got to know each other. “We were too busy shoveling coal into the furnaces, trying to keep the power on,” one editor says.
During the start-up’s final days, Finkelstein was so desperate that he even leaned on some of his well-sourced reporters, seeking contact information for potential saviors.
The site’s final day began inauspiciously when employees in California, protected by stringent labor laws, received unexpected direct-deposit paychecks for unused vacation days. That’s why “we knew it was coming,” ex-reporter Seth Davis wrote on X. But then the staff “waited all day for word from leadership,” he wrote, to no avail; reporters passed the time (and tried to cheer each other up) by sharing cute pet photos on the company’s Slack, and heard nothing definitive until The New York Times reported that the company was shutting down.
“I am not in the loop,” Wakeford wrote on Slack.
“LOL,” one staffer wrote.
“How long does our health care stay active?” another wrote.
Ex-Messengers are now figuring that out through their newfound online forum. In effect, the Slack group has become the staff directory the site never got around to creating. “I just found out that we had a TV critic!” one amused ex-reporter tells me.
The platform has provided a sense of closure: “There are all these moments of catharsis, realizing I’m not alone in this,” another ex-reporter says. “We’re now forever bonded by this traumatic experience,” says an ex-editor, who only met the previously mentioned reporter after both of them were laid off.
But they may have a hard time staying in touch if the Ex-Messengers are forced to disband. “The Slack trial is expiring at the end of the month,” a member says, “and everyone is too poor to extend it.”
Brian Stelter is the host of the Inside the Hive podcast, a former anchor of CNN’s Reliable Sources, and a former media reporter at The New York Times
