The Lifeboat to Save Sports Journalism

A rapidly evolving — or rather, disintegrating — media landscape is driving writers to newsletters

“It’s mine. It’s entirely mine. So few things are entirely ours,” journalist Will Leitch told me of his weekly bulletin, called This Here Newsletter.

Leitch made his name in sports and culture writing: He was the founding editor of Deadspin and still churns out regular columns for the likes of New York magazine and mlb.com. But with This Here Newsletter, which is approaching its 200th issue, Leitch now has an outlet to write about anything he wants: sports commentary, politics, and personal essays about his family. The only constant is Leitch’s autonomy.

A rapidly evolving — or rather, disintegrating — media landscape has left many writers out of regular paying jobs. With new publications shuttering seemingly every other month (most recently was Leitch’s former home at Deadspin, but that will likely change by the time you’re reading this), both freelancers and staff writers are often left in the lurch.

With newsletters though, they can’t be shuttered unexpectedly. They can’t fire everyone when there are whispers of a union drive; it’s rare to see them be bought up by a hedge fund and then loaded with debt. And they might not always pay, but they’re a guaranteed outlet with an audience that wants to hear what they have to say, which can sometimes be enough.

Leitch says he became disenchanted during his time at Deadspin when he had to start worrying more about advertising revenue and search engine optimization than actual writing. But with This Here Newsletter, that’s not a problem. “A newsletter lets me go as long as I want, or as short as I want,” he said. “I can go in-depth on any topic, or I can be quick-hit and silly.”

Many of us, I imagine, have at least one newsletter that pops into our email inbox each week. With platforms like MailChimp and Substack, it’s now easier than ever for anyone — not just professional journalists — to publish their own newsletters.

Sports writers in particular are finding a home on the medium. While many outlets that cover sports don’t see smart writing on lucha libre and ping-pong history as worth their time, there’s certainly a niche audience out there that devours that type of content. Game recaps that are finished before the final buzzer and PR-approved player profiles are the new norm in sports media. But a number of sports writers say they are now bucking that style of corporate access journalism, in favor of developing their own following.

“It’s been a passion for me to keep writing regularly without the constraints of anyone’s editorial calendar or mandates,” said Scott Hines of the Action Cookbook Newsletter, which covers sports. That sense of freedom seems to attract both readers and writers to newsletters. While certain publications can pigeonhole what a staff writer covers, in a newsletter, they answer only to the following they’ve built up. Those readers are often more invested in the voice and opinion of the individual writer than any given topic or area of coverage.

This deliberate, explicit commitment between reader and writer is a significant aspect of newsletterdom. No one stumbles upon a newsletter — you decide to opt in. The act of handing over an email, or taking out a subscription, is a vote of confidence that many writers take very seriously. As Alex Hancock of the newsletter L’Ultima told me, “People provide their email and have to trust you won’t use it nefariously, which requires a certain level of vulnerability.” But it also allows the writers to push boundaries they might not otherwise be able to. SBNation’s Matt Brown, for instance, started Extra Points to write about sports in a way that might not be welcome at his employer’s site. “Since I already know my audience is committed to me,” he said, “and they know what they’re getting, I don’t feel as bad about writing 2,000 words about something that’s less tenable for SBNation.”

Dwyer says monetizing isn’t just an option. “It’s the only bloody option right now. It looks like hell out there.”

That freedom is part of what drew Louis Keene to the medium. He recently launched a newsletter focused on the NBA’s Los Angeles Clippers, called Unstatable, which has allowed him to experiment with his own writing in a way that wasn’t possible as a pure freelancer. Keene now has formal press credentials with the Clippers, thanks to his reporting at Unstatable. “One thing I was struggling with […] was creating a readership that could identify my voice and would follow me around.” The newsletter gave him a sandbox in which to develop that voice.

One recurring trend through most newsletters is an unmistakable nostalgia for a version of the internet that no longer exists. Luke O’Neil, the writer behind Welcome to Hell World, said he began his newsletter because “I wanted to do the opposite of everything I have been made to do as a web writer and journalist my entire career. Instead of attention-grabbing headlines, opaque ones. Instead of concise and to the point writing, rambling and very, very long. Instead of easily digestible and clear, purposefully difficult and odd.”

Hancock echoed these sentiments, saying that, while the early internet may not have been any purer, “It did feel less commercial, less restrained by advertising metrics and the whims of men in suits.”

Kelly Dwyer has already implemented subscriptions for The Second Arrangement, and tells me it’s an integral part of his family’s income. “Nobody offered me a job when I was laid off,” he said. “This is what I have to do to survive.” Supporting a wife and two daughters, Dwyer says monetizing isn’t just an option. “It’s the only bloody option right now. It looks like hell out there.”

Others caution of a newsletter bubble. O’Neil compared newsletters to the other recent hot new medium, podcasts. He expects they’ll follow similar trends: “Way too many people will start them, some stars will break out and make a lot of money, some people, like me, will make a modest living, and most other people will just do it for fun as a creative project.”

Aaron Gordon, now a reporter at Jalopnik, created a minor phenomenon with his since-shuttered transit newsletter, Signal Problems. But when I asked if he thought others may be able to follow in his footsteps — to turn a newsletter into a more stable form of income — Gordon demurred. “I don’t think it’s necessarily wise for others to extrapolate from my experience,” he told me. Gordon thought his own success was more a case of catching lightning in a bottle — a confluence of events that could not be easily replicated without some measure of luck.

It’s probably naïve to think that anything can stem the hemorrhaging of jobs in modern media at this point, and newsletters likely aren’t a panacea. Still, the medium offers benefits for both readers and writers. For both parties, it seems to offer some sort of refuge from the worst tendencies of the rest of the internet, and for that, if nothing else, it should be valued.

“Money, cynicism aside,” Kelly said, “We’ve got to remember that people have to write for themselves.” And right now, newsletters might be the best way to do that.