Here’s a hypothetical for you.

Imagine that, somehow, I gained the unilateral power to name myself the Kansas City Chiefs’ starting quarterback in Super Bowl LVIII. (Maybe a genie granted me a wish? Or I’ve stumbled upon some truly devastating Andy Reid blackmail material? Pick your own explanation.)

Then imagine that in two Sundays, I — an out-of-shape 48-year-old with a noodle for a right arm and the agility of a roast beef sandwich — perform about as well as one would expect. I get sacked on every dropback, fumble on most, and generally make a mockery of the nation’s most popular sport. Patrick Mahomes spends the entire game on the sidelines, fuming. The Chiefs lose 89-0, the worst blowout in NFL history.

At the postgame press conference — assuming I retained enough unfractured bones to sit upright in front of a microphone — imagine this is what I say:

Well, obviously not the result we were hoping for. Credit to the Niners — they played well. I think the key factor was their defensive scheme — we weren’t expecting them to blitz their safeties so much on first down, and they showed some new wrinkles in zone coverage. I think it’s also fair to criticize some of Coach’s play calling, especially on third down. And the offensive line didn’t have their best game — I think they’d tell you that themselves. In the end, there was just too much against us to overcome.

Now, all those things might be true. Maybe the Niners did do some new and inventive things on defense. Maybe Reid called a few boneheaded plays, and maybe the o-line did have an off night.

But none of that matters, really. Because the real reason the Chiefs lost, in this hypothetical, is that I made an incredibly idiotic decision that was an obvious mistake from the moment it popped into my head. Fueled by my own arrogance and ego, I guaranteed that a group of incredibly talented and dedicated players would lose. No matter how well Isiah Pacheco runs, Justin Reid tackles, or Trent McDuffie covers, it won’t matter — because I have, for transparently stupid reasons, chosen to render their skills inconsequential.¹

I’m sorry if my hypothetical seems far-fetched. But is it really more far-fetched than what we just watched happen at The Messenger: burning through $50 million in just eight months by pursuing obviously terrible ideas for a news site — and then having the unmitigated gall to blame its problems on “economic headwinds“?

The self-appointed quarterback here was Jimmy Finkelstein, the 75-year-old “veteran media investor” who came up with the idea for The Messenger. He declared the site would fulfill “an important mission” and serve “as a legacy” from him to the world. Remember the monoculture days of yore, when the family gathered around the TV set Sunday nights to watch Morley Safer and Harry Reasoner? The Messenger was going “to help bring those days back.” And it would do it with raw W-2 tonnage, promising a newsroom of 550 people within a year of launch, not to mention $100 million in revenue. The rest of media was broken, you see, and only the “impartial, independent, accountable” Messenger could right the ship, offering “balanced journalism in an era of bias, subjectivity and misinformation.”

That The Messenger was a dumb business idea was strikingly clear before it launched, even before it bought and shuttered a better news site. At the risk of saying “I told you so,” I told you so. (And I was far from alone.) I won’t repeat all the issues I wrote about last May, but to hit the highlights:

• The era of monetizing traffic swells with generic network advertising is looooooong gone, to the extent it ever existed. Platforms don’t send traffic like they used to, and while programmatic ads can add cashflow, they can’t support the sort of high-cost structure of a 550-person newsroom. (Much less one that burned literal millions leasing high-end office space in three cities that stayed largely empty.)
• That traffic-chasing strategy led to a massive reliance on aggregating other outlets’ stories in a way that always made the brand feel cheap. The literally hundreds of copy-and-paste pieces a day obscured whatever reputation the site’s original content might be able to build. Getting to The Messenger’s stated goal of 100 million monthly uniques on that strategy was doomed from the start.
• At a time when sustainable news is all about identifying the right niche, Finkelstein declared The Messenger’s niche would be, roughly, all human activity. Politics! Sports! Celebs! Business! Tech! That grand sweep made tremendous sense for a 20th-century newspaper, and it can make sense for their 21st-century digital successors. But a digital news startup has to pick a lane, and The Messenger picked all of them.
• There is no evidence of a large market demand for what Finkelstein (with sidekick Richard “Mad Dog” Beckman) labeled “unbiased” news, but which was clearly meant to be more of a right-leaning site that would treat his good friend Donald Trump as a normal candidate for office. There is a reason the funders behind its $50 million are Republican megadonors, not media people. (Fun fact: We learned yesterday of yet another 70-something conservative activist billionaire who was an investor in The Messenger: John Catsimatidis, former Republican candidate for mayor of New York City.) And when the depths of The Messenger’s failure became clear, the only people interested in doubling down — in a meeting at Mar-A-Lago! — were folks like Tucker Carlson’s backer and the ex-CEO of Parler.
• Even if the desire for a real “unbiased” site was real, Finkelstein was profoundly ill-suited to lead one. He is, after all, the man most responsible for laundering John Solomon’s Ukraine nonsense into the media mainstream. He’s one of Rudy Giuliani’s closest friends, an old Trump pal, and a longtime protector of his Republican allies in his publications.

Where The Messenger would end up was deeply predictable. The signals were clear before the resignations, before the SEO madness, before we learned it basically forgot to make any money in its first year. (Total 2023 revenues: $3 million. Net loss for the year: $38 million. Its only consistent advertiser last fall was one of its own investors.)

Which is why it is both comical and infuriating to see Jimmy Finkelstein blaming his failure on those “economic headwinds” and all the ills facing the broader news industry. No, Jimmy — this is on you. The broader economy is doing good-to-great, and there is little about the state of media economics today that wasn’t foreseeable a year ago.

Let’s be clear about this. The Messenger was Finkelstein’s self-conceived “legacy” project. It was born out of his bizarro nostalgia for a media universe long gone. It was his fundamental misunderstanding of web traffic that tied its strategies in knots. (Finkelstein loved to brag about The Messenger’s big pageview numbers — without recognizing the site’s overall web traffic was on par with mid-sized regional newspapers and niche sites with 15-person newsrooms.)

When Finkelstein says ruefully that he’d “exhausted every option available…to raise sufficient capital to reach profitability,” he’s also saying that he didn’t want to put any more capital into such an obvious money loser. After all, he may not be a billionaire, but he’s no street urchin, having sold one of the businesses he inherited from his dad Jerry, The Hill, for $130 million in 2021. (“Mr. Finkelstein’s net worth, amplified by securities trading, was never disclosed, but his lifestyle made no mystery of his wealth. He held parties at his art-filled Manhattan triplex and his oceanfront Southampton estate attended by movie stars, magnates and city, state and federal officials.”) If he really thought his “legacy” was redeemable as a business — and given that much of the $50 million The Messenger raised was from others — he could’ve stood by his bet and its “important mission.”

It was his choice to give zero severance to the 300 people whose employment he eliminated Wednesday, many of whom had left perfectly good jobs based on a vision that was never going to come to fruition. It was his choice to stiff people out of their vacation time (unless they lived in California, where that’s illegal). It was his choice to cut off the health insurance of laid-off staffers and to blank the website within hours. (The site currently shows only its logo and an email address; I haven’t heard back after sending it a message seeking comment.) In each case, he could afford to be better — or even, to quote the slogan Finkelstein’s wife coined for her boss Melania Trump at a White House gig he arranged for her, to “be best.” (He was reportedly pulling about $1 million a year out of the company in salary and expenses as The Messenger’s CEO — a job no one would give him in a free market.)

But here’s the thing: Finkelstein will be fine. Sure, The Messenger’s flop will probably sneak into the first paragraph of his obituary. But he’ll still have his (and his dad’s) fortune, the oceanfront Southampton estate, the waterfront West Palm Beach condo, and a lot of politically powerful numbers in his phone. But the one thing we can do is make sure the blame for this episode doesn’t get shuffled off to “economic headwinds.” He’s the guy who had the hubris — the decadence — to name himself starting quarterback and ran a good team into the ground.

1. And, presumably, make Taylor Swift sad. [↩]