‘Deliberately Cruel’: Staffers Torch ‘Sociopath’ Jimmy Finkelstein Over Messenger Implosion

Photo Illustration by Luis G. Rendon/The Daily Beast
Photo Illustration by Luis G. Rendon/The Daily Beast

Following doomed media startup The Messenger’s spectacular flameout on Wednesday afternoon, journalists suddenly left without a job are calling owner Jimmy Finkelstein a “sociopath” for the “deliberately cruel” manner in which he handled the closure of the “centrist” news site.

The Daily Beast spoke with a dozen insiders and now-former employees about the final tumultuous days of The Messenger and the aftermath of its implosion. These sources asked for anonymity to speak freely, noting that they are now currently looking for jobs within the media industry.

After the bloodbath, one Messenger insider told The Daily Beast that “Finkelstein made sure the process was deliberately cruel to the staff.” Many staffers agreed with that notion.

Ex-Staff at The Messenger File Class-Action Lawsuit Against Shuttered Website

“I think he’s a sociopath. I don’t know what would possess you to do that?” a former editorial staffer sighed. “I cannot fathom putting people in a position where they have to learn that they are losing their jobs and their health insurance from a newspaper.”

Another breaking news reporter added that “basically the entire working environment there was cruel,” citing “the expectation of how much they were basically making us write” and “the push for traffic.”

Others disagreed that Finkelstein was exhibiting intentional cruelty but nonetheless blamed him for the news site’s demise.

“I think he was just overconfident and incompetent. He wanted something that doesn’t exist anymore. He hired a bunch of very talented people and did not let them practice their talents,” one member of the visual team said, noting that he thought Finkelstein had a “vision of, like, days gone by.”

“It’s like if someone bought a stable full of champion thoroughbred racehorses and used them for a pony ride and then sold them all to a glue factory.”

While Finkelstein is currently facing much of the staff’s fury for leaving hundreds of employees in the lurch with no severance pay or health insurance, editor-in-chief Dan Wakeford has also come under fire for his lack of robust communication with the newsroom and admittedly being “out of the loop” when word arrived that the site was shutting down.

Though Wakeford has at least engaged with furious employees publicly, expressing regret over the “devastating” demise of The Messenger, Finkelstein remains silent. In fact, he has yet to issue a public comment about the class-action complaint filed on behalf of terminated Messenger employees on Thursday evening.

Finkelstein did not respond to our request for comment for this article.

Launching The Messenger in May with a $50 million investment, Finkelstein and president Richard “Mad Dog” Beckman—who departed his role in early January due to “health concerns”—boasted right away that the site would bring in impossibly high online traffic and generate $100 million in revenue by the end of 2024.

Saying the duo overpromised and underdelivered would be an understatement. Basing their business and editorial strategy on an antiquated model of social-media-driven traffic and low-paying programmatic online ads, The Messenger burned through nearly all of its funding by the end of 2023, leaving the company with just “weeks” to live and in desperate need of a cash injection.

A photo illustration of Jimmy Finkelstein underneath The Messenger logo
Photo Illustration by Luis G. Rendon/The Daily Beast/Getty

After finally acknowledging the truth about the site’s money troubles and laying off nearly two dozen staffers, Finkelstein held “emergency meetings” with staff in early January and told them they would have updates on his fundraising efforts within two weeks. Though he complained that media reports about The Messenger’s struggles were spooking investors, he still expressed optimism that he would be able to secure enough money to keep the site operational.

In the end, the next time The Messenger’s staff would hear from Finkelstein was his email on Wednesday afternoon letting them know that the site would be closing shop—which came moments after The New York Times and other media outlets (including The Daily Beast) reported that the decision was made.

Finkelstein’s email, in which he blamed the “extraordinary challenges” and “economic headwinds” facing the media industry, was accompanied by an FAQ document informing fired employees that they’d received their last paycheck, they wouldn’t get severance pay, and their health insurance would cease.

The Messenger Didn’t Bother to Tell Staff Before Shutting Down

In a final insult, employees were also told to return their company-owned laptops. Within hours, the site’s homepage had been nuked with no access to the thousands of articles published in the past eight months. (Since then, staffers have been given passwords to access the archive, but the site remains offline.)

Though staffers confessed they had mentally prepared for weeks that the site would likely blow up, one reporter said that it still was shocking how it all ended. “It was such a cruel, harsh, and cold way that we would just find out from other outlets and then everything was shut down,” the reporter said.

Additionally, many employees feel like Finkelstein just saw the site as a “pet project” that he soon tired of, especially as it became clear that it wasn’t panning out as he hoped.

“I do sometimes wonder if he got bored of it. If it didn’t end up being like the great little late-career ego boost he thought it would be because it immediately got like, before it was launched, it was getting made fun of in the New York Post,” a reporter said.

“Yeah, you know, a lot of other media reporters have speculated he used it as his own personal piggy bank,” a staffer declared, pointing to a recent Puck story about Finkelstein’s reported million-dollar CEO salary and his lavish expenditures. “Part of me is inclined to agree, but another part of me is like, this was just a passion project for him. This was a scrapbook like, this was some bullshit hobby for him. And then for the rest of us, like it was our livelihoods that he was playing with.”

Another reporter concurred. “I keep telling people that this is like this was a pet project for Jimmy,” the staffer continued. “You know, it’s very clear that this was something that he just like, woke up one day and envisioned, ‘I’m going to take a stab at it. I’ve had luck with it in the past, and I’m going to do it again.’ It’s like such mediocre confidence. You know, it’s a hubris. It’s ridiculous. But for us, it was like our only stream of income and he doesn’t realize that.”

But senior staffers who were privy to Finkelstein’s last-minute negotiations to either sell the site or bring on additional investors disagree with the notion that he was either cruel with his actions or did not care about the staff.

“Look, I think all of us believed Jimmy would get the money. All the execs truly thought that. I know those last few days were in total limbo,” one senior staffer claimed, adding that the final update on the site’s fate didn’t come in until Wednesday afternoon.

“I have to give him this. He fought until the last minute. Instead of having two weeks’ severance, he used those two weeks to try and save that company and get money and to try and get a deal for those people,” another member of management stated. “It’s not like he’s a cartoon tyrant or terrible person. Like, he does care about people and so it’s not as cut-and-dry.”

At the same time, these senior staffers acknowledged that the refusal to update anxious employees, especially as they were frantically demanding answers, was a complete failure on Finkelstein’s part. And it was all due to the media mogul’s own ego, one source said.

“It is all about Jimmy all the time. And he didn’t listen to us,” one senior staffer noted, likening him to a “mini-Trump” who refused to heed any advice.

“I mean, it was appalling,” the senior staffer added. “You had every single member of management try to tell him how to do it… And it’s just like they’re all advising him to try to make things better for him. And he’s still—his automatic answer to any idea that came through is no.”

Wakeford, meanwhile, is also facing employee criticism in the wake of the embarrassing closure of the site. Having been described as “MIA” and “checked-out” by staffers due to his lack of visibility to the newsroom, the ex-editor-in-chief came under fire in the past few months over his silence amid calls for an employee town hall over concerns about the site.

In recent weeks, after Finkelstein was finally forced to hold “emergency meetings” after reports that the site was facing extinction, Wakeford did begin sending out morale-boosting editorial emails to the entire newsroom. Some staffers who had known Wakeford previously noted the change.

“In the last month, he was much more active, like he was much more involved in the senior editors’ meeting, he was being much more proactive in suggesting stories,” one editor noted. “He started to meet with the various verticals. I don’t know if he’d threatened Jimmy, but it was like I was, ‘This is the Dan I know.’”

Senior staffers, meanwhile, noted that Wakeford’s lack of communication with the rank-and-file staff was a directive that came directly from Finkelstein, who, they said, was keen on micro-managing everything related to the site and told Wakeford to only communicate directly with senior editors.

“I do feel bad that Dan is taking a lot of heat because he was bullied relentlessly by Jimmy,” one insider added.

Wakeford took to his LinkedIn account on Thursday to express sorrow over the “devastating news about the end of The Messenger,” adding that his focus was on trying to help get his colleagues jobs at different media outlets.

James LaPorta, an investigative reporter impacted by the shuttering, replied that “your comments here on LinkedIn and in news outlets recently makes up the majority of the communication I’ve seen from you as editor-in-chief in the eight months that I was at The Messenger.” In response, Wakeford agreed, saying “I’m sorry, it was out of my control and it was very frustrating.”

Responding to a request for comment from The Daily Beast, Wakeford reiterated his LinkedIn message, adding that he was “incredibly proud” of the staff.

Many staffers say what they’d like now is for Finkelstein to pay up and make it right.

“Pay us our severance from your own pockets, if you truly are so devastated, just pay us from your own pockets if you actually care,” one reporter proclaimed. “But the thing is, people like Jimmy don't even know, like, what the cost of a milk carton is right? Like, they have no idea what it’s like to live paycheck to paycheck.”

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