Jon Greenberg, AM’07, is the founding editor of and a columnist for the Athletic, the online publication purchased by the New York Times in 2022 to provide the bulk of the paper’s sports coverage. After finishing his degree in UChicago’s Master of Arts Program in the Humanities (MAPH), Greenberg worked as a columnist for ESPN and as the executive editor for Team Marketing Report before joining the fledgling Athletic in 2016. His comments have been edited and condensed.

How did the Athletic decide on Chicago as one of its original markets?

The cofounders, Adam Hansmann and Alex Mather, were looking for a market to launch in. Chicago was atop their list because of the Cubs. They (correctly) reasoned that they should start in a city that had a team with championship aspirations.

So they contacted me out of the blue on LinkedIn, and it came at a fortuitous time. I had recently found out that ESPN wasn’t renewing my contract. It’s crazy how much the company has grown, going from a real start-up (a few employees, no money) into the behemoth you see today. I can say I was there when it was just an idea.

How did your time at UChicago influence the work you do now?

Honestly, I wasn’t sure I was going to stay in the program early on. Not because it wasn’t interesting or useful, but I was still working full time. Then I stepped into Dan Raeburn’s creative writing workshop and knew it would be worth my time (and money). It was Raeburn’s first-ever class, and was a special group led by the best teacher I’ve ever had. He helped me grow as a writer and as a reader. I wrote a lot about my hometown and my preteen years, much of it having to do with sports and identity. I carry those themes into my work today.

About two years after I graduated, I got a job as a columnist with ESPN. I really believe the writing I did in his class allowed me to break out of my rut and find myself as a writer.

Why sportswriting instead of other genres?

The kind of sportswriting I’m drawn to is stories about people: feature stories about legends, stories about loss, stories about those on the margins. I love to write about people who have made careers in sports on their own. In a world of nepotism and elitism, I want to write about small-town kids making it in the big city. It’s obviously because that’s how I see myself, but I think those kinds of stories are universal.

I joke that some people in town got famous writing about Michael Jordan—and I write about the late great overnight radio host Les Grobstein and Chicago beer vendors. Those are the kinds of people who interest me. I’ll read anything that has a good hook and helps me learn more about the human condition.

What about sports journalism today bothers you the most?

My biggest complaint is how the owners and leaders of sports journalism publications were so unprepared for the future of the media. It’s also partly why I was confident in the two founders of the Athletic, because they didn’t come from the world of journalism.

Aside from that, it’s mostly the lazy aggregation that passes for news these days. Then again, a lot of that dreck stems from bad leadership and the calamitous state of the media business. I have plenty of other concerns, from the nonstop news cycle to the dominance of team-affiliated media in the modern era, but it’s all too complex to summarize. Maybe I should do a podcast?

Have you ever made a prediction or assessment in your writing that ended up being completely wrong?

Oh yeah, a ton of them. I once went on ESPN radio’s flagship show Mike & Mike before a Cubs home opener and declared that Mike Quade would be a good Cubs manager. I wrote it too. Man, was I off. He was a disaster. Occasionally, I get some things right.

What are your favorite venues to catch a game in Chicago?

Really, it’s just Wrigley Field. They’ve modernized it, but they haven’t ruined it, thankfully.