A Hoosier Reinvents Online Sports Coverage—Again

Once one of the internet’s most influential sportswriters, Lafayette’s Kelly Dwyer has decided to create his own site from scratch. The first step? Attempting to fix what’s wrong with web journalism.
It’s a cold night in Indy, but inside Bankers Life Fieldhouse, the players on the floor sweat heavily as they zip up and down under LED lights. The Pacers and Celtics are joined by 16,000 fans, plus one more slice of humanity: the sportswriters.

Most media types don’t sit courtside at the Fieldhouse. Instead, they occupy some tables and chairs up by the luxury suites, and tonight there are journalists from the AP, The Indianapolis Star, a few local TV stations, and the Boston outlets still sending writers on the road. Almost all of them have their laptops open and tuned to TweetDeck, but one scribe sits with only a legal pad. His name is Kelly Dwyer, he lives in Lafayette, and he can honestly claim to be one of the pioneers of online sportswriting.

Dwyer leans forward, his arms folded, and watches the action closely. Even at 37, he sports a spiky haircut that’s more punk rock than press row. While the other sportswriters focus on tweeting micro-updates and observations, Dwyer doesn’t even pull his laptop out of his bag, much less use it to update his 40,000 followers. “You’ve got to look down to do that,” he says. “I don’t want to look down.”

Dwyer has always done things differently, building his reputation on an ability to notice strange and delightful things during a basketball game—and then to describe those things in jittery and metaphysical prose that’s more Walt Whitman than Adrian Wojnarowski. It helps that Dwyer has watched, by even a conservative estimate, more than 30,000 basketball games. Still, he keeps discovering new things to love. On Pacer Victor Oladipo and his fondness for playing in Indiana: “There’s a lightness there now,” Dwyer says. “It used to be all hard angles.” On Cory Joseph and his attempts to be the perfect teammate: “He’s going to be one of the worst head coaches ever or one of the best head coaches ever.” On Myles Turner and his unrefined ability: “He doesn’t know yet who he is as a player, as a person, as anything. And that’s cool.”

While those observations might sound perfectly tweet-able, Dwyer isn’t interested in that. Last year, after a decade of writing and editing at Yahoo!, he got laid off. Instead of pursuing another full-time job, he decided to launch The Second Arrangement, a one-man website that offers readers a simple proposition: For $5 a month, they can wake up most mornings to a long essay in which Dwyer recaps every single NBA game from the night before, along with tangents on comedy, music, and whatever else interests him. When ESPN’s Zach Lowe, arguably the best sportswriter working today, tweeted out the site’s unveiling, he captioned it simply: “KD IS BACK.”

And so he is, taking in games here at the Fieldhouse or on his laptop in Lafayette and then writing about them until dawn. Dwyer isn’t just a godfather of internet sportswriting. He’s someone who is attempting a bold experiment in digital journalism. Yet he can’t shake the feeling that his profession and his medium have fallen into some dangerous ruts—that they’ve become too specialized, too formulaic, too fixated on giving readers exactly what they want. “I think this whole internet thing,” he says, “got away from us.”

The modern internet emerged in the mid-’90s, a mix of personalized blogs and professional sites like Salon, in addition to some sluggish old-media outfits. Sports were there from the start. In 1996, ESPN’s nascent website hired a writer named Rob Neyer, and his baseball blog shaped a generation of sportswriters. (“The guy who really changed the way that I thought about sports,” Zach Lowe has said, “was Rob Neyer.”) They were also influenced by the debut of technologies like YouTube (2005), Twitter (2006), and the iPhone (2007). Taken together, these factors changed the way fans consume sports and sports media alike.

None of this is surprising. But it’s still crazy to consider how quickly it happened. In 1996, the same year Neyer joined ESPN, the New England Patriots signed an undrafted kicker named Adam Vinatieri; in 2006, the same year Twitter launched, Vinatieri jumped to the Colts. His NFL career, in other words, is basically as old as online sportswriting—and Vinatieri is still kicking.

So, for that matter, is Kelly Dwyer. While Dwyer was born in Chicago, his family moved to Lafayette in 1995. Theirs was a middle-class household with a high-tech twist: Dwyer’s mom worked in IT, so they got IBM computers and dial-up internet earlier than most. And young Kelly loved it. “I printed out reams of NBA stats from the ’70s and ’80s,” he recalls, “just because I could.”

During his senior year at Lafayette Jeff High School, he started emailing with the proprietor of OnHoops, one of the early NBA websites, and contributing posts of his own. Dwyer watched every game he could pull over the air from Indy and Chicago, plus the national ones on cable. His bedroom was buried in VHS tapes of games he wanted to study later.

It didn’t matter to Dwyer that he lived in a town with a top college hoops program. (Even today, he focuses only on the pros; when Brad Stevens became the Celtics’ coach, Dwyer had to have a colleague catch him up on Butler’s tourney runs.) The NBA was the only league he cared about. When it came time to do a final project in his English honors class, he made an almanac with bios and scouting reports for each of the association’s 400-plus players, then published the whole thing at OnHoops. Dwyer even faxed player questions to the various teams, though he didn’t get much response. At least the Celtics called his house to tell him they couldn’t talk because they were busy prepping for the playoffs—although his dad had to take the call since Kelly was still at school.

College came next, but after two years at the University of Missouri, Dwyer moved to Chicago in 2000 to write for more websites, including Fox Sports’s and later Sports Illustrated’s. Dwyer also bartended because, even during the dot-com boom, analyzing sports online was an unproven and precarious way to make a living. “It was a wilderness,” he says. “It was the frontier. It was like the 19th century, and you get to Wyoming and you’re like, I guess this is Wyoming?”

By this point, fans could order NBA League Pass through DIRECTV, which gave a diehard like Dwyer access to virtually every game. Along with sportswriting’s other early adapters, he kept refining the voice that still powers much of the internet today: smart but loose, personal but funny, open to statistics and okay with not having every answer.

Dwyer’s prominence grew even more once he founded Ball Don’t Lie, Yahoo!’s influential NBA blog, in 2007. The site fused the style of Dwyer and his colleagues with Yahoo!’s fire hose of traffic, and suddenly it seemed like everyone was reading their silly riffs and discussions of teams’ points per possession—not just the NBA’s fans, but its players, its front offices, even its owners. (In 2015, Cleveland owner Dan Gilbert allegedly got Yahoo! to delete a post in which Dwyer had jokingly referred to the Cavs’ home as “Predatory Loans Arena The Q,” referencing the Quicken Loans-sponsored stadium.) Ball Don’t Lie popularized the basketblogger approach until it was popping up on SportsCenter and NBA TV, where today some of the site’s alums host a beloved show. “Everyone now does what we did,” Dwyer says.

But over time, Ball Don’t Lie wore Dwyer down, though he blames himself for this more than he blames Yahoo! and its corporate demands. Dwyer moved back to Lafayette and eventually settled down with his high school sweetheart and her two daughters. He hoped Yahoo! would give him a more normal 9-to-5 life, and it did for a while. But the job also left him feeling stale and replaceable, trapped in a cycle of writing and editing and chasing the same five stories as everyone else. “It was just chaotic,” Dwyer says, “throwing content at the internet constantly.” Last summer, his phone rang one afternoon and he saw his boss’s boss on the caller ID. He knew it was over. Yahoo! had decided to fire him and several other sportswriters.

The company gave him a severance, and Dwyer used part of it to get out of Indiana—to take some road trips with destinations no more defined than see the ocean. “I had to close the laptop,” he says, and that time in the car helped him clear his head. He realized that his problems with writing for Yahoo! might be true of the internet more broadly. “It’s an obligation now,” he says of so much online sports coverage, with its rigid dance of insider-y writers and insider-y readers. “Everything is an obligation to prove that you saw the same things everyone else saw—to say, ‘Oh yeah, I was there, too.’”

In particular, Dwyer worries about younger writers—today’s versions of him, cold-emailing that editor at OnHoops. “We’ve got too many people with too many voices in their heads,” he says. Too many writers, especially young writers, must worry about slapping together some quick analysis of breaking news or burrowing into their ever-narrowing niche. There’s less time to write weird, to write for love, to write, as Dwyer puts it, “as if no one’s ever going to read it.”

Dwyer is quick to point out that he has made many of these mistakes. (“This is all coming from the guy who didn’t listen to his own advice,” he says.) But he also hopes his new home, The Second Arrangement, can provide a concrete example of how to do things differently. In fact, his independent website is also a deliberate alternative to the internet. “It’s more like a late-night show,” Dwyer says. “Funny and funky and quick. It’s something to scroll through instead of Twitter while you’re waiting on your significant other to finish in the bathroom.”

When the site launched in November, The Wall Street Journal published a story showcasing it as an example of the niche, subscription-based content creators emerging online. A company called Substack hosts The Second Arrangement and collects payments, taking about 10 percent as its cut. Dwyer told the Journal he needed about 1,000 subscribers to match his salary at Yahoo!

While The Second Arrangement occasionally carries Dwyer’s features and columns, his NBA recaps remain its soul. Some games get shorter write-ups, some get longer ones, but they all fit into an ongoing conversation animated by Dwy-er’s personality. On December 9, for instance, he marveled at Lance Stephenson, the Pacers’ prodigal: “Lance is a playoff ticket for the price of a regular season seat. He palms the ball in his right hand and the Indianapolis crowd in his left.” Two days later, Dwyer revisited this theme: “Lance Stephenson is an E-Ticket ride at Indiana Beach prices, and you’re allowed to bring a cooler in.”

Already it’s clear that Dwyer is doing exactly what he wants to with the site. “I went into this thinking I’d have to fight off boredom, covering all those games,” he says. “It’s been the opposite. Now I just need to figure out how to make the car payment.” Dwyer’s not sure The Second Arrangement will ever allow him to do that. So far, its subscriber base hasn’t come close to earning him even a modest living. NBA fans love the free samples he shares, but it’s been hard to get them to punch in their credit card. “I might be a little ahead of things,” Dwyer says.

There have been a few promising examples of subscription-based sports sites—dkpittsburghsports.com, bostonsportsjournal.com, and The Athletic’s city network—but they tend to center around a location or a franchise instead of an individual voice. And The Second Arrangement isn’t doing dozens of daily updates on your team’s moves. Honestly, it’s doing the opposite. It’s offering a subscription to Kelly Dwyer’s brain.

Back at Bankers Life Fieldhouse, that brain is observing, arguing, and amusing itself. On a typical day at The Second Arrangement, Dwyer wakes up in the late afternoon and then works all night at his kitchen table, toggling between NBA League Pass games on his laptop and his phone. After the layoff, he canceled his cable to save money, so if there’s a game that’s blacked out, he heads to a bar or a friend’s house. Once the last West Coast game ends, sometime after 1 a.m., he grabs a quick nap and then writes until the sun comes up.

Yet there are also days where Dwyer leans on the connections from his time at Yahoo!, lines up a press pass, and attends a game in Indy or Chicago. Dwyer may be an NBA League Pass wizard, but he’s also an advocate for seeing basketball in person. There are too many things, he says as Lance battles several Celtics for a rebound, that you’ll never appreciate on a screen. “These players,” Dwyer says, “these assets, have to preserve themselves to be at their best on ABC in June.” The sarcasm clings to that word, assets, even as the NBA’s long seasons and predictable contenders are something fans have accepted. Still, Dwyer prefers to seek out the moments where the league surprises. “Being wrong just means there’s more basketball you need to watch,” he says.

Right about then, Boston’s Kyrie Irving jumps out on a fast break, only to see a whistle bring it to a halt. Coach Stevens’s strict rotations mean that, without even looking at the bench, Irving knows he’s coming out for a breather. So instead of handing the ball to the ref, the Celtics’ star keeps driving toward the basket and tries something strange—an improbable angle, an insane amount of spin, a layup that clanks violently off the rim.

The whole time, Dwyer is mesmerized. He doesn’t see a pointless, dead-ball miss. He sees a small but glorious subversion, an athlete opening himself up to instinct and pleasure and play. Kyrie isn’t entertaining the fans so much as he’s entertaining himself, and these flickers of strangeness are what keep Dwyer’s obsession alive. “You’ve got to find something,” he says, “to keep yourself going.”