Kelly Dwyer, NBA raconteur, goes his own way

Substack’s second customer fires up The Second Arrangement

When we think of the ideal Substack publishers, we think of people who can reflect and inspire passion among a core group of readers. Few writers fit the bill better than Kelly Dwyer, who we consider one of the great NBA writers today.

Dwyer came up in the late nineties and early aughts by building a cult following around Behind the Boxscore, a column in which he reviewed every single NBA game every night of the season. It’s not exactly the sort of thing you’ll see in your local paper. Dwyer’s known for his wry observations (“The first thing we pulled out of our stocking this year was Gordon Hayward’s antipodal ankle”), cutting insights (“He’s Hunan Shrimp”), and ruminative paeans to under-appreciated beauty (“It’s getting cold now, so you look to what warms. The leafy ones, still clinging”). He’s the closest thing to a beat poet anywhere near the NBA. “One of the most talented people I’ve ever worked with,” ESPN’s Adrian Wojnarowski has said.

Today, Dwyer, a journeyman whose travels have taken him through, Sports Illustrated, and Yahoo Sports, is launching his own thing: a subscription publication to free his expansive mind from the shackles of click-mad chicanery. It’s called The Second Arrangement. The tagline: “I rise when the sun goes down / cover every game in town.” It sits, in the parlance of the Hot-Take Economy, at the intersection of the NBA and Steely Dan. With the arrival of The Second Arrangement (subscribe) comes the return of Behind the Boxscore, emailed to subscribers at the end of every basketball night. And there’ll be more: features, podcasts, and other drips of sweat from Dwyer’s keyboard to bring relief to the league.

Dwyer, who lives in Lafayette, Indiana, started Behind the Boxscore for (RIP) in 1999. “I was already up, already watching this stuff, already taking it in,” he says. “Already coming home from college parties with shitty lager on my breath. I’m that addicted to it.” He wanted something that would quench an unquenchable thirst for the game; something that informed and entertained. Something more than boilerplate. “That’s what I wanted to read, so that’s why I started writing,” he says. The column was an extension of an obsessive streak apparent in his work from a young age. At 12, he wrote a biography of Queen based on liner notes from the band’s CDs. At 17, he wrote a thousand-page NBA almanac with biographies of every player. “I am terribly miscast as an orthodox writer.”

His go-deep-and-weird approach to writing has probably cost him some money over time, but it has maximized his credibility. When Dwyer landed his Sports Illustrated column at age 24, he did it for free. His wife’s hairdressing work paid the bills. He graduated to $150 a piece, but his main income came from tending the bar at a Best Western alongside a lounge singer whose nightly masterwork was a drum machine-backed rendition of Lady in Red. Collared shirts; aprons; wine bottles on the ties. “That’s the low-point bar,” he says today. “It has not been easy to be a sports writer.”

In June, Dwyer was laid off by Yahoo, where he had worked on the Ball Don’t Lie blog since 2009. “It was my dream job,” he said at the time. “I wanted it for life.” Reflecting on the call that ended his employment, Dwyer says it was rough. “It was deadening for a second. And then I drove to the hair salon and waited for my wife’s blue eyes to show up, and then we had a little cry.” In the months that followed, he did normal-person things: traveled around the state; got a library card; focused on being a better husband and dad. The job market for sports writers didn’t look encouraging. ESPN, Sports Illustrated, and Fox Sports, to name a few, were laying off writers by the dozens. Clickbait ruled the day.

Dwyer saw a better way. He wanted to write for an audience that paid him directly. That way, he could write what he wanted, how he wanted, and on a schedule that made sense. He wouldn’t have to worry about ads getting in the way of his words, and he wouldn’t have to fret over pageviews. “I’m sick of having my column show up fifty-second because I didn’t write the headline right,” he says. He envisages The Second Arrangement as a “themed conversation” between him and his readers. It will have an intimate feel; unvarnished. No bullshit. Just Dwyer, his words, and his readers.

“I want to be driving really fast in a slow car,” he says. “I want people to be able to feel the road with this one.”

We couldn’t be happier to help him step on the gas.

Subscribe to The Second Arrangement.