Despite falling flat on his face with doomed media outlet The Messenger, Jimmy Finkelstein is already looking to launch another project, multiple sources familiar with the situation told The Daily Beast.
The former owner of The Hill recently met with potential investors in New York, according to three sources familiar with the matter, in an effort to drum up interest in a new venture. This potential new project is still very much in the planning stages, the sources emphasized.
Details are still scant on what exactly Finkelstein may be cooking up, with sources speculating that it could be health industry-related and possibly not even a traditional media company.
ADVERTISEMENT
Either way, the 76-year-old mogul does appear determined to add another chapter to his lengthy career. “Jimmy is definitely doing something. He's not prepared to be on the sidelines,” one person close to Finkelstein told The Daily Beast.
Another source close to the situation relayed last month that Finkelstein was in New York City, meeting with potential investors and promising to soon launch a project with the potential to clear his name after The Messenger’s spectacular failure. Finkelstein did not respond to multiple requests for comment.
Finkelstein has recently met with Loews CEO James Tisch and Newsmax chief Chris Ruddy to discuss his ideas, our sources said.
Tisch was a key investor in The Messenger, the $50 million “centrist” news site that launched last spring before crashing and burning less than a year later, leaving hundreds of journalists out of work.
And Finkelstein and Ruddy have a friendly relationship. Following The Messenger’s abrupt closure, the financier mentioned to outgoing staffers that he could help them land jobs at Newsmax, our sources said. However, not many journalists seemed eager to jump to the MAGA cable outlet.
Neither Tisch nor Ruddy responded to requests for comment.
Additionally, The Messenger’s former chief digital officer, Rory McCafferty, has been involved in his former boss’ journey back into the media game, according to our sources, one of who described McCafferty as “Finkelstein’s wingman.” Indeed, before working at The Messenger, McCafferty was the senior vice president of digital at The Hill for nine years, until departing in 2022 shortly after Finkelstein sold the outlet. And before that, McCafferty served as VP of digital at Prometheus Global Media, a media company co-owned by Finkelstein until its sale to Guggenheim Partners.
Jimmy Finkelstein and Ben Smith speak on stage during the Semafor Media Summit on April 10, 2023 in New York City.
Michael Loccisano/Getty Images for SemaforFinkelstein’s desire to get back into the media business is no surprise, considering his voracious appetite for wading into current affairs. The septuagenarian exec has long hosted off-record Zoom chats to gather “experts” to discuss and debate various topics, our sources said. Branding the calls “Finkelstein & Friends,” the mogul acts like the host of his own private talk show, moderating and steering the discussion.
Starting before the launch of The Messenger, Finkelstein held these calls weekly on Sundays and was occasionally joined by the outlet’s top editors, prominent Republicans, and businessmen. Finkelstein has occasionally used these calls to woo potential investors into his media projects, our sources explained.
Weeks after The Messenger's implosion, which featured a “brooding” Finkelstein getting pilloried in the press and by his jilted ex-staffers, the media executive—who boasts of his longtime friendship with Donald Trump—portrayed himself as a victim while simultaneously claiming he had “absolute confidence” that the site “would have been profitable” if he could have just raised $20 million more.
“So I think that our model—which everybody decided on their own was an old model, it’s just not their model—was working,” he insisted to Axios in February.
In a separate interview with The Hollywood Reporter, Finkelstein took issue with the reporter asking how the collapse of The Messenger would impact his overall legacy. “Talking about legacy it is interesting how you are writing from a publication whose greatness I created. I was Chairman of The Hollywood Reporter. When I bought it, it was a few pages of newsprint with a tiny web site that no one read. When I sold it it was one of the great publications in America,” he told THR, adding: “I have always taken publications and grew and improved them.”
Though Finkelstein may be looking to prove the naysayers wrong with yet another new project, he is still staring down a slew of lawsuits from former Messenger employees accusing him of reneging on severance packages and back pay.
One day after their unceremonious firing, The Messenger’s now out-of-work staff filed a class-action lawsuit alleging the company violated the New York labor laws by not providing severance pay and other benefits with its abrupt closure.
Since then, a series of top executives and editors from the failed startup have sued Finkelstein for welching on employment contracts promising termination packages worth hundreds of thousands of dollars. One of the lawsuits also accused Finkelstein of protecting his pals, including Trump, by restricting “negative coverage” of his friends on the site. Meanwhile, a freelance writer who began working for The Messenger during its final months filed a complaint last month alleging that he never paid his wages before shutting down.
In the end, the laid-off journalists launched a GoFundMe to raise $50,000 to help their most vulnerable colleagues pay the bills and get health insurance. While Finkelstein still hasn’t paid any severance, he did call the online fundraiser “wonderful.”
