Conversations with former employees, however, suggest that an even bigger flaw was Finkelstein himself, a fiddling, meddling presence in the daily production of Messenger journalism — a guy who distracted and flustered his staffers with every last directive.
With his intrusive behavior, Finkelstein finds himself in good company in American media these days.
To accomplish his nitpicking, the 75-year-old Finkelstein relied on phone calls and emails. And boy were there a lot of emails. One former deputy section editor of the now-defunct site received 1,300 interventionist emails from Finkelstein between early July and the site’s demise. The first of that series arrived in the early-morning hours of July 8, 2023 — a summer Saturday when there wasn’t much going on.
At 6:21 a.m., Finkelstein got creative with his top staffers by sending them a link to a story on the Messenger that touted “five soothing podcasts” to facilitate some weekend lounging. Ever the clever motivator, Finkelstein delivered a note alongside the link: “This is not the idea. People need to stay on mission.” Later that morning, after he noticed that the site’s politics section had almost no traffic, he wrote, “Do we have anything coming up that’s worthwhile”?
An editor sent him an inventory of some “fresh accountability” work in the queue. Finkelstein wrote back, “Eh …” So the editor sent a fuller list of upcoming stories, to which Finkelstein replied with a data point based on Chartbeat. “14 people on politics,” he lamented.
Now we know what a traffic hound does when he has no traffic — he pouts. Finkelstein learned to love clicks in a previous role as part-owner of the Hill, a publication that under his direction seemed to pop up in every newsy Google search. “When I was at the Hill, we did 125 million visits a month,” Finkelstein said last spring at an industry confab. Some of that traffic came from folks who ate up stories by the Hill’s John Solomon, who cranked out rickety, conspiratorial material about alleged dirty dealings by Joe Biden relating to Ukraine. (Solomon left the Hill in 2019.) A 2017 report by Harvard University’s Berkman Klein Center for Internet & Society highlighted the Hill’s role as a much-visited clearinghouse for political news.
Perhaps all those numbers got into Finkelstein’s head. Early promises and projections for the Messenger hinged on miracles: It would earn $100 million in revenue in 2024 (it pulled in $3 million in 2023, according to the New York Times), it would amass a newsroom of 550 journalists, and it would reel in 100 million monthly readers. Would it fix your printer, too?
The route to this runaway commercial success would be an unbiased presentation of the news, as Finkelstein promised before launching the Messenger. Feeding neutral or centrist news to the underserved market of Americans allegedly thirsting for an alternative to partisan sources is an ambition that predates the Messenger. CNN host Michael Smerconish in 2022 riffed about a news network dedicated exclusively to “independent thinkers,” and the 2020 launch of cable channel NewsNation rested on the same down-the-middle premise.
It all sounds great in principle, though behind-the-scenes tensions at the Messenger speak to complications in execution. “Jimmy was spending time fuming and sort of tone-policing, what headlines would say, what the mix was on the homepage,” said Marc Caputo, a former member of the Messenger’s politics team, on a podcast with fellow former colleagues. “But you’re a businessman. Focus on the f—ing business!” Former journalists at the Messenger tell me that Finkelstein was constantly pushing for this story or that story to be added to or removed from the homepage, usually in the interest of achieving the balance that was so key to the site’s identity. “One of his obsessions was the homepage and making sure it wasn’t too anti-Trump,” said one former reporter.
Another said this: “Jimmy’s idea of objective news is news without context.” And context is seldom friendly to former president Donald Trump. With any luck, the Messenger’s downfall will end the faux-visionary chatter about centrist news, an unattainable ideal that breaks down whenever its propagators are forced to identify what constitutes centrism. And as for the audience for down-the-middle news — sure, most people want unbiased coverage, but they also want free coverage. Who’s to say the non-paywalled site wasn’t just attracting extremist cheapskates?
An old pal of Trump’s, Finkelstein would often urge action on his political hobbyhorses, including the possibility that former first lady Michelle Obama would swoop in and secure the Democratic presidential nomination.
The Messenger’s rank-and-file staffers insist that they teamed up like an offensive line to block Finkelstein’s forays and prevent them from steering the site’s offerings. At least one of the founder’s blitzes broke through, however, as when a top editor directed colleagues last November not to allow any more coverage of Trump’s civil fraud trial in New York to “slip” onto the homepage. A spokesperson for the Messenger told the news site Semafor that the messages in question were being “misinterpreted.”
What requires no interpretation whatsoever is that Finkelstein acted as a drag on the very property that was supposed to ensure his legacy in American publishing. On the editorial side of the Messenger, Finkelstein hired people such as Dan Wakeford (decades of experience leading top magazines), Michelle Gotthelf (20-plus years at the New York Post), Marty Kady (a former “lifer” at Politico) and other news industry veterans. What a deal these folks had: Finkelstein paid them handsome salaries … and then provided daily assistance with homepage decisions!
Messenger journalists pride themselves on their coverage of Trump’s legal woes, New York Mayor Eric Adams, the rise of House Speaker Mike Johnson and the Taylor Swift-Travis Kelce relationship, among other stories. Don’t go looking for them, though, because management mothballed the site.
The bigger point here? Good journalism doesn’t persist without good ownership, as news organizations are learning elsewhere in the country.
Kevin Merida left his job as executive editor of the Los Angeles Times less than three years after taking it, a parting of ways triggered at least in part by disagreements with owner Patrick Soon-Shiong and his family. As reported by the New York Times, Soon-Shiong, a billionaire doctor and entrepreneur, intervened in discussions on how the paper would cover another billionaire doctor who was an acquaintance of Soon-Shiong’s (the paper said Soon-Shiong was seeking “truthful, factual reporting”). Merida also reportedly alienated Soon-Shiong with his decision to bar Los Angeles Times journalists who signed a Nov. 9 protest statement — which slammed Israel for the “killing of journalists in Gaza” and ripped coverage of the conflict in Western media outlets — from participating in coverage of the story for at least 90 days. (Soon-Shiong told his own paper that he was “disappointed” not to have been informed of the decision.)
In a statement, Los Angeles Times spokeswoman Hillary Manning said the paper’s executive editor reports up to owner Soon-Shiong. “He respects the independence of the LA Times newsroom, believes in letting the journalists do their jobs and does not interfere with editorial decisions. That will not change,” reads the statement.
As I noted earlier this week, David Smith, executive chairman of Sinclair Broadcast Group and the new owner of the Baltimore Sun, was outed last month as the backer of a lawsuit against the Baltimore school system — a topic of extensive reporting by Sinclair’s flagship station in Baltimore, WBFF/Fox45. This wasn’t a media mogul meddling with the staff, it was worse — a media mogul meddling behind the scenes in local politics. Fox45 had to slap embarrassing disclosures on long-since-published stories on the suit.
So do we have a trend toward meddling media execs?
There are still plenty of solid owners in American journalism — people who help set their organizations’ strategy and values, leaving the day-to-day news decisions to their editors. As the industry becomes more and more impoverished, however, bidders for its properties might bear less and less resemblance to the stolid, iron-spined owners of reporters’ dreams. In other words, there’ll be plenty to cover on the media beat.
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