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Three Newsrooms Imploded Around Me In Under A Year

STILL LIFE OF SKELETON WRITING IN LARGE BOOK WITH QUILL PEN (Photo by H. Armstrong Roberts/ClassicStock/Getty Images)
H. Armstrong Roberts/ClassicStock/Getty Images

I covered the NFL for three media outlets in the last calendar year: Football Outsiders, The Messenger, and The New York Times. Two of those outlets died. The third got rid of its entire sports section. I am forced to conclude that I am the grim reaper, harbinger of doom, the herald of the sports media apocalypse. Or maybe the industry’s just broadly and systemically broken, and I happen to have especially rotten luck. You can decide.

It is March 1, 2023, an hour before a soggy sunrise. Winter rain in Indianapolis aims directly for your socks. If you are coming down with a cold, the back of your throat feels like steel wool. If you are not coming down with a cold, wait a few hours. I am freezing, wet, congested, and hung over. My credit card is ready to crack under the strain of my balance. My most recent paycheck never arrived. I am covering the NFL Scouting Combine, the league’s combination trade expo/fraternity rush, for Football Outsiders. 

Aaron Schatz founded Football Outsiders in 2003. I came aboard as a regular contributor a year later. FO grew into a well-respected analytics boutique, even as Schatz ran the website on a shoestring budget for over a decade. He then sold it to a data company called EdjSports in 2018.

EdjSports poured some money into FO but also spent extravagantly on side projects and promotional gimmicks, like a pick-the-winners gambling app which never worked, and an expensive commercial (complete with director, makeup artist, and an all-day location shoot at a tavern, with me and others flown in on company expense) which never aired. Some Canadian investors calling themselves Champion Gaming gained control of EdjSports in a “reverse-takeover” late in 2021. These wannabe Wolves of Bay Street promptly fired about two-thirds of the EdjSports staff and shuttered the brick-and-mortar headquarters in Louisville. When that wasn’t enough to cauterize the financial wounds, they simply stopped paying their bills and answering their phones.

By the start of 2023, excuses became more regular than paychecks: 

  • The Jan. 15 paycheck was delayed “due to an unforeseen delay in the TSX Venture Exchange approval to close a financing,” according to an email from Champion Gaming; Martin Luther King Day was offered as a bonus excuse. 
  • “Unfortunately missed the wire cut off with the payroll provider for tomorrow's payroll,” company CFO Cameron Graham wrote on Feb. 14. 
  • There is no paper trail of excuses for the March 1 missed payroll, but a March 15 email explained that paychecks would again be several days late because Champion was allegedly acquiring another sports media outlet, and “there are many hurdles with regards to regulatory approvals that we have diligently been working on and navigating.” That other outlet was as real as the dog who eats homework. 

Champion Gaming stopped paying freelancers altogether sometime before the end of 2022. The top contributors were each owed several thousand dollars by March. These longtime writers issued ultimatums and took their grievances public. But we all kept writing: To those of us who had been there most of our adult lives, Football Outsiders felt like as much a family as a business, and we all wanted to keep it alive. 

In Indianapolis, I confided the precarious state of Football Outsiders’ finances, and my own, to a trusted friend. I told him that I felt obligated to be the last man standing: Schatz and I would go out like Butch and Sundance, firing off statistical analyses in a blaze of doomed glory.

“Are you using loyalty as an excuse to avoid something that makes you uncomfortable?” my friend asked, both of us knowing the answer. 

I accepted that Football Outsiders was on hospice, not life support. It was time for an exit strategy. My twofold plan:

  • Wait for Football Outsiders to lay everyone off, then collect unemployment and use that cushion to catch my breath; and
  • Increase my workload at The New York Times. After all, it’s not like they were suddenly going to stop covering sports or anything.

My mother, an octogenarian stroke victim with a brain tumor, suffered a minor fall last January. The family spent the spring preparing her physically, mentally, and emotionally for a new life at as cheery a senior care facility as we could afford. Those preparations, most of which fell upon the least employed member of the immediate family (me), were largely in vain. But by lunchtime on the day of the extraction, mom’s hysteria had simmered down to anxious exhaustion. Eager to establish a new normal, we were about to tuck into some cafeteria grilled cheese and tomato soup when I received a call I needed to take: a job offer from a brassy, well-funded startup called The Messenger.

I was unemployed. I was not collecting unemployment, however. Football Outsiders technically still existed, though no one had received a dime since April. The handful of remaining full-timers were still technically employed, except for me: I formally and publicly resigned on April 30. 

The good thing about a public resignation is that it gets attention in an attention economy: The NFL internet knew that I was on the market. The bad thing about a public resignation is that it’s proof that you quit, rather than getting laid off. Quitters don’t get unemployment benefits, even if their former employer only exists as a stack of bills on the table of a would-be captain of industry hiding somewhere in Ontario from an ever-increasing number of process servers.

I had first spoken to folks from The Messenger in early May, just days after leaving Football Outsiders. I spoke to them again two weeks after that, and again two weeks after that. The individuals I was speaking to, veteran editors from The Athletic and Sports Illustrated, were clearly coping with some difficult bureaucracy above them; it’s never a great sign when a startup must deal with its own bureaucracy long before it starts dealing with customers. 

The margins in media are tiny. The only outlets that can afford chunky infrastructure are those with both unimpeachable name recognition and an established, successful subscription model. The Messenger had neither. The New York Times, on the other hand, had both.   

My first big break in the industry, back when I was still a high school math teacher, came when the Times assigned me to write weekly game previews for the 2008 NFL season. I got a full page in the prestigious Sunday edition for a princely $250 per week. The lofty-profile gig led to full-time writing opportunities, so I left the Times (and teaching) in 2012, eventually landing at Bleacher Report and staying there for many years.

Then came the pandemic. In the spring of 2020, while ESPN was showing replays of the 2013 Cotton Bowl and sportsbooks were taking action on soccer matches from Turkmenistan, Bleacher Report laid off many of their veteran writers as part of a pivot from written expression to emojis. I fielded the “bring your playbook” phone call minutes after a fender-bender in the ShopRite parking lot, two weeks’ worth of groceries foraged from half-empty shelves still in my trunk. 

Fortunately, the Times remembered me and took me on for a midweek column at a competitive rate. I kept the Times gig even when Football Outsiders elevated me to full-time status in 2021. When FO paydays became cross-your-fingers days in the winter of 2023, New York Times payments appeared like clockwork. When I explained the fate of Football Outsiders to my Times editors after that morning of clarity in March, they began carving out space in the freelance budget for a coveted, semi-lucrative Monday recap column.

As The Messenger dallied throughout the spring, making me wonder just how airtight their business model was, my wife and I sold ourselves on the idea of cutting household costs so I could spend a year as a gentleman newspaper beard-stroker. Perhaps I could write a book or learn woodworking, or at least shave 20 points off my systolic. So on the day The Messenger made an offer, the day we not-quite-dragged my dear mother not-quite-kicking (though there was a bit of screaming) to assisted living, I asked for time to consider it. If the Times could come within range of The Messenger’s offer, I would err on the side of stability. 

Four days later, while visiting mom and explaining how to use the new television remote for the fourth or fifth time, my phone started buzzing convulsively. The New York Times had just announced that it would be outsourcing nearly all sports coverage to The Athletic, which it purchased in 2022. The news was confirmed by email from my assigning editor that began with “Well…” So much for that. I accepted The Messenger’s offer. It would still take them several anxious weeks to make anything official.

Media companies give out MacBooks the way Olive Garden doles out breadsticks. Bleacher Report issued me a laptop in 2014. I FedEx’d it back to them unused in 2020. EdjSports gave me a laptop in 2021. I returned it in May of 2023 to the home address of a 20-something Champion Gaming “employee” who had not been paid in weeks so that he could drive it to the storage facility which housed the cremated remains of Football Outsiders.

The folks at The Messenger handed me a MacBook on Aug. 1, my onboarding day. That laptop is still buried under paperwork somewhere in my office as I write this. Three hundred employees at about a thousand dollars per fancy laptop equals a whole lot of wasted money, though not as much wasted money as unused 25th-floor office space in a building one block from the World Trade Center.

Laptops as party favors? Check. Cavernous, nearly-empty offices? Check. I knew on my first day that The Messenger was a money incinerator, and not destined to last. The site was already earning a reputation for churning out piles of Florida Man Strangles Middle School Teacher He Followed on OnlyFans–type clickbait. And I learned why it had taken weeks for me to officially get hired: CEO Jimmy Finkelstein insisted on ceremoniously approving every single hire after listening to a formal request from their editor, as if he were some ancient monarch hearing petitions by emissaries from Hattusa. By the time I signed on, seven figures per month were going up in flames, with almost no revenue trickling in, while Finkelstein pretended he was J. Jonah Jameson.

None of that mattered to me. I had a job.

Sportswriters have become like the elderly: Most of our conversations are really condolences. When your company goes to the great elephant graveyard, your pals text you how sorry they are. When your pals are replaced by AI three weeks later, you return the texts. We always offer to do anything we can for each other, usually with a caveat: I’ll ask here at FantasyBurp, but we just laid off 70 people on Tuesday. When you find a job, you climb into the listing lifeboat, and everyone you know asks if there are any seats left.

By the time the NFL season started, I knew that The Messenger had no coherent editorial, promotional, financial, or even SEO plan: just high-minded talk about “centrist” politics (which seemed to mean Pretend Donald Trump is normal), a vague sense of how web traffic was monetized circa 2006, an army of talented writers chained to aggregation duties, and a college freshman’s budgeting instincts. 

Still, it had taken nearly two years for The Turk to come for Football Outsiders after the Champion Gaming acquisition and about the same amount of time for The New York Times/The Athletic to realize they were competing against themselves. I figured The Messenger could last at least half that long. I also assumed that the investors would stick it out until the 2024 election, whether for practical or nefarious reasons: No self-respecting rich guy would pull the plug on his vanity project until he at least had a chance to damage society on its way down.

I severely underestimated The Messenger’s self-destructive capabilities.

Jan. 5, 2024: In the wake of a round of layoffs and reports that The Messenger would run out of money at the end of the month, Jimmy Finkelstein addresses the company department-by-department on Zoom. He appears on screen slouching sideways, his seated torso visible, his head craning into the screen at a 45-degree angle, as if the camera is perched on a nearby milk crate. 

Finkelstein exudes all the energy and confidence of Eeyore. He calls reports of the company’s dire straits “broadly accurate” but vows to try his darndest to raise an additional $20 million, casually mentioning that reports of a recent meeting with potential investors at Mar-a-Lago were also accurate. The Friday afternoon pep rally is as reassuring as a nature documentary about polar bear habitats.

Two days earlier, the NFL had approved my Super Bowl credentials. Taking a calculated risk that rebranding Tucker Carlson’s Messenger would take more than a month, I book a non-refundable flight to Las Vegas.

Jan. 12: Editor-in-Chief Dan Wakeford sends a staff email promising financial updates soon.

Jan. 22: Wakeford sends a staff email promising financial updates by the end of the week.

Jan. 26: Wakeford posts on Slack that the updates would actually come the following week.

Jan. 29: Seeing the end of January approach and tiring of senior management’s monthlong recreational waterboarding, Messenger staffers begin demanding straight answers. Wakeford announces that we will hear something later in the week.

Jan. 30: The NFL sends an email announcing last call for media hotels. Taking a calculated risk that even a two-week notice of a shutdown would now encompass the Super Bowl, I book a non-refundable room at the Excalibur for eight days.

Jan. 31: The Super Bowl coverage team meets at 3:30 p.m. amid apocalyptic rumors. We discuss logistics and plans in language usually heard at Irish wakes: If we but live to see tomorrow, we shall drink together in the land of gold and whiskey

A New York Times article lands in the Slack channel as the meeting is wrapping up. We’re done. News of The Messenger’s death reached the Times news desk before its own, which would be a multifaceted problem if anything mattered anymore. The Super Bowl meeting wraps like the victory party for a candidate down by 40 percentage points. Finkelstein’s email, headlined “DIFFICULT NEWS,” reaches my inbox shortly after.  

The Messenger didn’t merely shut down operations. It scrubbed most of the evidence of its existence before the end of the business day. Articles posted and promoted hours earlier vanished. Links returned a white screen with “The Messenger” and an email address in king-sized black type; no archives remained. The company Slack channel, where fretful colleagues had posted pet photos for hours on that final day, shut down before many of us even received Finkelstein’s this-got-hard-so-I-quit missive. I imagine Finkelstein stopped just short of ordering the fire alarm pulled at the Manhattan office and locking the door behind everyone. 

Only a zombie Twitter account shambled on, posting pre-scheduled content. The head of the social media department had been shoved out the door with everyone else. “I could kill [the scheduled posts] now and spare the embarrassment,” this person said in a Slack channel cobbled together by and for the recently unemployed. “I thought leaving them might be fun, and the last sign or proof that any of us had anything to show for our work.”

Which brings us to today. I am at home, not in Las Vegas: the NFL rescinded The Messenger’s press credentials, leaving me up the creek for my expenses. There’s an ex-Messengers Slack channel in one window of my computer, and a Discord for ex–Football Outsiders writers and readers in another: two ghosts who follow me. There’s a fresh unemployment claim filed with the state. I have another MacBook to return to a company that no longer exists. Nearly everything I have written in the last year has vanished. I have become a phantom.

The media industry is a carcass getting picked clean by scavengers. The business models that made sense even five years ago no longer work. There are too many entrepreneurs seeking riches that were never there, too many SEO farms covering every web search with unreadable kudzu, too many social-media moguls treating links outside of their fiefdoms as an act of treason. The whole system is now so gamed that readers have a hard time finding good information or entertainment, while informative and entertaining people cannot find readership. It’s a hostile environment for consumer and producer, and it’s not getting better.

I love this work. I am good at it. But I cannot afford to sign on with another hedge-fund dink who has startup capital burning through his cargo shorts and some vague ideas about scale. I can’t bear another round of thanking readers for reaching out on social media after another employer slipped out of town in the dead of night. I cannot stomach another morning waking up to do a job that I am not even certain will still exist by the end of that day. My only choice, as I see it, is to work for someone I can trust not to sell the farm out from under me: myself

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