Jimmy Finkelstein, the veteran media investor, former owner of The Hill, and recent founder of digital news start-up The Messenger, prefers to stay at one of two places when he comes back to New York. The first is the Harvard Club, the 129-year-old members-only joint in Midtown. (His wife, former CNN producer Pamela Gross, is an alum.) The other is The Carlyle, to which Finkelstein invited me after I twisted his arm into sitting for an interview. When I arrived at the storied hotel on Tuesday morning, about 20 minutes late because traffic on the Upper East Side was a nightmare, The Messenger’s chief communications officer met me out front and took us up to her boss’s suite, where the towering (literally) 74-year-old tycoon greeted us in a black suit and purple tie.
I had talked to Finkelstein, who spends most of his time these days in Palm Beach, at different points over the years, usually when his name was in the mix to buy some storied journalism institution that had fallen on hard times. (See: the Daily News; Time Inc.) This was our first in-person encounter. He’s mild and soft-spoken, to the point where I worried about his voice registering on my recorder, which I placed on a coffee table accompanying the couch into which Finkelstein lowered his 6-foot-4-inch frame. He told me his parents had lived in The Carlyle for 10 years and that he had a sentimental connection to the place. “I know so many of the people here,” he said.
On to the subject at hand: The Messenger had lifted off just more than a week earlier, with $50 million in funding, a $100 million revenue projection for 2024, and big plans for a 550-person newsroom. The prelaunch phase reminded me of the buzz preceding The Daily, the Rupert Murdoch–made iPad “newspaper” that chugged along for almost two years in the early 2010s—a lot of money and manpower being poured into a venture that people couldn’t quite wrap their heads around. But whereas The Daily debuted with a carefully choreographed, high-gloss presentation at the Guggenheim, with Murdoch onstage beside Apple’s Eddy Cue, The Messenger entered the world as a sort of beta-mode work in progress, essentially ironing out the kinks in real time.
There’s no sugarcoating it: The reception among the media cognoscenti was downright savage, perhaps a little too savage (and a little too gleeful) considering this is a place hiring oodles of journalists (including some prominent ones) at respectable salaries, on the heels of a brutal season of layoffs that rattled publications far and wide. Reports about three editors handing in their resignations as if storming off of a content farm haven’t helped matters. (Gregg Birnbaum, a CNN and NBC News alum, excoriated the site for its “rapacious and blind desperate chasing of traffic” on his way out the door.)
I read Finkelstein a few sentences from Joshua Benton’s widely circulated takedown for Nieman Lab: “The thing that’s confusing about The Messenger to everyone else in the media world is that its ideas don’t make any sense. It’s in an aggressive sort of denial about the world of digital news publishing in 2023. It’s LARPing an earlier time. The Messenger thinks it will reach 100 million monthly uniques on the back of bland aggregation…. It thinks it can support a 550-person newsroom on programmatic advertising. The Messenger thinks the right pitch for a site funded by Republican mega-donors and run by the guy who brought the world John Solomon is: ‘We’re the unbiased ones!’”
Finkelstein countered with an adamant response: “I sold The Hill a year and a half ago.” (To Nexstar for $130 million.) “The Hill made about $18 million [in profit]. We had 120 million visits on average a month, with about 70 reporters and 90 people in the editorial department. Clearly, it wasn’t impossible, because we did it. Now we’re not only gonna have as large, if not larger, a political [audience], but we’re also gonna have sports and business and general news. So, I mean, it’s hard to imagine that we can’t do it.”
What seems to be tripping people up, I suggested, is that The Messenger’s hefty cost structure belies the mass-traffic CPM strategy it appears to be dabbling in, especially in a landscape where advertising-supported digital brands are, to put it mildly, having a rough go of it. Here’s where Finkelstein wanted to set the record straight. He gave me an earful about the business model he’s been hammering out with Richard Beckman, The Messenger’s president (as well as a memorable and controversial personality from the glory days of Condé Nast, who worked with Finkelstein both at The Hill and on Prometheus Global Media’s reinventions of The Hollywood Reporter, Billboard, and Adweek.) Addressing the barrage of early criticism, Finkelstein said, “Nobody bothered to ask about the model!”
Fair enough, so let’s hear the guy out. Programmatic advertising—that’s the cheap and automated stuff—is just one piece of the puzzle, said Finkelstein, whose official title is chairman and CEO. Direct sales will begin this summer, as The Messenger rolls out verticals including news, politics, business, sports, entertainment, technology, health/wellness, food, travel, and style. “We’re going after very large advertisers. We expect to have tens of millions of dollars in direct sales in the first year.”
Events will follow in September, among them thought-leader gabfests in Washington led by a former events director from The Hill whom Finkelstein recently hired from Semafor. (The Hill, according to Finkelstein, made more than $5 million a year on events, and that was just in the politics space.) Newsletters are coming soon, starting with a general newsletter, a politics newsletter, and on and on. Ditto digital “TV shows,” which will appear on YouTube and themessenger.com. (Finkelstein said The Hill turned a profit of $3 million a year on one show, a daily political roundtable called Rising.) And—surprise!—The Messenger is eventually going to introduce a “premium” component that readers will have to pay for, the exact scope and content TBD. “There will be a lot of areas for revenue,” Finkelstein said.
In a March 10 interview with The New York Times, Finkelstein remarked, “I remember an era where you’d sit by the TV, when I was a kid with my family, and we’d all watch 60 Minutes together. Or we all couldn’t wait to get the next issue of Vanity Fair or whatever other magazine you were interested in. Those days are over, and the fact is, I want to help bring those days back.” In an introductory post, The Messenger’s editor in chief, Dan Wakeford, formerly of People, described the site’s mission as “demystifying the onslaught of misinformation and delivering impartial and objective news.”
I told Finkelstein I had a different impression of The Messenger. My impression was that it would be more akin to dailymail.com (speaking as someone who’s not ashamed to admit he reads the Mail every day), with a populist, right-of-center editorial perspective; a target audience of regular folks, as opposed to elites; and a mix of scoops/original reporting and super-high-octane aggregation, like a candy bowl full of must-click headlines.
“Your impressions are wrong,” Finkelstein countered. “To start with, it’s not center-right. One of the things I do is look at the brand to make sure it is right down the middle. That people on the right can respect it because it’s true, and people on the left—”
Okay, let’s put the “right of center” language aside; what I meant to suggest was that The Messenger feels like it’s aiming to be something of a robust digital tabloid, no?
“Not a tabloid,” Finkelstein countered again. “That’s a mistake. It is a very serious publication that will also have lots of fun articles in it.”
As more journalists come on board, according to Finkelstein, the amount of aggregation will decrease; he said there was already “less” of it on the site than at launch. Also, the more frivolous fare will get its own section. “We’re gonna create a little site within the site. It won’t appear on the front page, but it will be on the site for those people who are interested.”
Bottom line, per Finkelstein: “It won’t be like the Daily Mail.”
For its maiden voyage on May 15, The Messenger set sail with a nonconfrontational but nonetheless news-making Donald Trump Q&A. It was conducted by the veteran Florida journalist Marc Caputo, late of NBC News and Politico, now The Messenger’s national political reporter. I couldn’t help but wonder if Finkelstein himself had wired the interview, given his long-standing friendship with the former president and current Republican front-runner for 2024.
“I had nothing to do with it,” Finkelstein said. “Caputo got it and it was all his.” What’s Finkelstein’s relationship with Trump like these days? “I didn’t speak to him for a long time after January 6. Like many people, I was very upset. I had a dinner with him many months after that, and I saw him at two parties in Palm Beach. But if you look at my background, Joe, I’ve given more parties for Chuck Schumer than for my wife. I’m friends with Carolyn Maloney, who was head of the oversight committee that investigated Trump. I was friendly with Harry Reid. I could go on and on. I’ve been around a long time.”
Long enough that Finkelstein can remember being in the same room, as a very young man at the 21 Club eons ago, as Bobby Kennedy, Nelson Rockefeller, and Martin Luther King Jr. It was around the time that Finkelstein’s older brother, Andrew Stein (he shortened the surname), was entering Democratic politics. Stein would go on to serve as a New York assemblyman and Manhattan borough president. Their father, Jerry Finkelstein, was remembered in his 2012 New York Times obituary as “a self-styled Democratic power broker” who “made a fortune in business, real estate, and newspapers.” The elder Finkelstein began his career as a reporter at the New York Daily Mirror—a long-since-defunct Hearst tabloid and pet obsession of mine—before lording over publications including the New York Law Journal and The Hill, both of which Jimmy would later run. (He bought a controlling stake in The Hill in 2014, years after his father had sold it.) “I grew up in a world of politics. I grew up in a world of business. I grew up in a world of media,” said Finkelstein, who has five kids of his own—ages 20 to 50—from three marriages.
In his youth, Finkelstein lived at 812 Park Avenue and attended the prestigious Deerfield Academy in western Massachusetts before moving downtown for college at NYU, where he studied history and economics. He then embarked on a path of private equity and media investing, putting his stamp on publications as varied as the Star Tribune in Minneapolis and Dan’s Papers on the east end of Long Island. (Finkelstein still has a place in Southampton.)
I noted that he has remained more under the radar than his brother and father. (The man doesn’t even have a Wikipedia page.) “I just didn’t enjoy flying above the radar,” Finkelstein told me. He swore this was only the second proper sit-down he’d ever agreed to, the first being for that story from the Times in March. “Can we end it now?”
Not so fast. What I really wanted to know was why, after unloading The Hill for $130 million, he didn’t just cash that check and spend his golden years maxing poolside.
“It didn’t take me long, Joe, to get bored.” He read. He swam. He took long walks. Then he got restless and made a play for the Miami Herald, but McClatchy wasn’t having it. “I tried to buy that maybe for three months,” Finkelstein told me. “I thought I would use it as a base, expand it in Florida, and then bring it national. That didn’t work out.”
Finkelstein decided it would be “harder, but no more expensive,” to start something new than to buy an existing property. He wouldn’t tell me how much of his own money he kicked into the initial $50 million funding round—which also includes capital from James Tisch, CEO of Loews Corporation, and Josh Harris, cofounder of Apollo Global Management, where Finkelstein worked back in the day—but he hinted that it was “a lot.”
The Messenger will almost certainly be Finkelstein’s swan song, the capstone to a long career in media and finance. I asked him to play devil’s advocate and imagine we were talking a few years down the road, with The Messenger not having survived. Blame it on market conditions, or a recession, or ChatGPT killing digital advertising or whatever, but let’s just say the site went kaput. Would it still have been worth it to him?
“Totally,” Finkelstein replied.
Why?
“I think it’s an important mission. I didn’t do this just to make money. There are plenty of things I could have done to make money. I’m doing this as a legacy, and if it doesn’t succeed—which it will!—obviously I’d be disappointed, but I would say I’m happy I did it.”
This article has been updated to correct a transcription error.
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