Iwas born in Fort Worth, Texas. I went to Paschal High School in Fort Worth, and its claim to fame is that it’s the alma mater of Dan Jenkins and Bud Shrake, who both wrote for Sports Illustrated.
Sportswriting seemed like a very tangible career in a way that writing the great American novel did not.
My mom might be able to confirm this, but the first time I talked about wanting to be a sportswriter was about second or third grade; I got benched on the little league baseball team. My previous dream was to play for the Texas Rangers, and I sort of did a calculation and realized that probably wasn’t going to happen. And the next best thing was to become a sportswriter. So I wanted to do it really, really early, and I never wavered from that.
I was advised early on, everyone has that one person in your life who says don’t major in journalism, major in something else, which is why I majored in political science.
On his first taste of the journalism field
[Reporter-Researcher] was a glorified internship with the New Republic. It was an internship with a grandiose title.
My mom was a high school counselor, and she’d always say in a measured way, ‘You know Bryan, if you decide to become a journalist, starting salaries are about $18 to $20 thousand a year.’ Then she’d say, ‘If you want to become an astronaut or a lawyer, the starting salary is higher.’
I proved her wrong — because I made $13 thousand a year. I had this great strategy where I paid one bill a month; one month it was my TV, one month it was my rent.
I wrote a couple of political stories there, and I helped fact check articles. It was during the 2000 campaign. I think the main reason I got that job was I was a Texan and George Bush was running for president. I think they figured a bullpen of Harvard and Yale all-stars wasn’t going to be able to tell them as much about George W. Bush as I could. Not sure I actually did, by the way, but that was the theory.
[My first breakthrough] was when the editor of Play called me, and asked me if I was interested in writing the media column for Play, and it was going to be this quarterly magazine inside of the New York Times.
I think I was 27. I don’t want to inflate it, but I think that was the moment when I thought I actually belonged, rather than being someone who was a pretender who was fooling people all the time. That feeling would soon return, though. It never goes away.
Play was a sports magazine and I was the media writer, so I’m writing a piece about Tony Kornheiser after he gets the gig on Monday Night Football. I wrote about Bob Costas. At this point, I’m pretty much a ‘sportswriter.’
On what he learned throughout his early career stops
[New Republic and Slate] were places that were really interested in idea-driven stories. You were sort of a columnist much more than a reporter. So almost everything I did early on was try to think of sharp ideas, better ideas, and very little had to do with reporting. Journalism should be about meeting people, and not just doing Nexis searches all day.
Back then, [Slate] would say, ‘Go do a 100-plus page Nexis dump on Tom Brokaw, and write me 800, 850 words that makes an argument on his place in TV news.’ And that was the job. Those were really fun to write and they were fantastic training as a writer.
The editor wanted you to take a magazine profile, and instead of writing the whole profile, he wanted you to write the nut graph. He stripped away the interviews, the scene where you have salad with Brokaw, all the calls to his friends and associates; you just literally wrote the three to four paragraphs of the piece where they tell you what the piece is really all about. It was a really interesting exercise.
On Grantland
Speaking of those idea-driven pieces, I had written one about Bill Simmons in 2006, when his Red Sox book came out. And I was writing a column at Slate called the Middle Brow, which was about luminaries such as Larry the Cable Guy.
Bill’s book comes along, and everybody was like you should definitely write about Bill. So, I wrote up a column about Bill, we became email correspondents. A couple of times a year I’d send him an email saying he wrote a good column, and once in a while he’d send me a note and say the same thing. But I never met him, and I didn’t know him other than that.
When he started [Grantland], he asked me to pitch him some ideas, and I did, and then that led to a small contract. After a year or so, that led to a full-time contract.
The hardest thing to wrap my mind around was, the editors from Bill on down were asking us what we wanted to do. ‘What do you want to write and how do you want to write it?’
In journalism, you’re so used to filling boxes. ‘This is what an 800-word Slate piece looks like, please write your own version of it.’ At Grantland, they were asking a totally different question. That was the hardest thing for me to wrap my mind around, and I’m not sure I ever did. I got better at it towards the end, but sometimes that’s the hardest thing to do. When you have that much freedom, to figure out how to do it. How to find your way.
[Grantland worked because] it was a mix of the editors guiding us along, the fabulous writers that they picked, and kind of rolling the ball out on the court and saying, ‘You guys do your thing.’
I think it was just a lot of conversations with editors about what was interesting and what was someone else not covering. We had so many people. So, all I was trying to do was do pieces that were really, really different.
I started writing about the media again in the last couple of years I was there in earnest. And I really enjoyed that. I wrote about Bob Ryan, I wrote some pieces about TV guys, and I found that to be really fun.
[Grantland’s end] was a two-stage thing. One was Bill leaving the company in May and the other was Grantland shutting down in October. I think if you didn’t see the latter as a very distinct possibility after the former, you were pretty blind.
I always had this weird feeling that any job that was that much fun isn’t going to last forever. I was proven wrong every day I was there because they were terrific to me, but I had this nagging feeling.
My wife and I had our second child and I was still in the maternity ward when I found out they were going to close it in October. I was upset, but I guess I couldn’t really be that upset.
We had ESPN contracts that lasted to the end of the year, or I did at least. So, it wasn’t like I was penniless. Eventually I started talking to Bill, about what he wanted to do next. It wasn’t a huge period of wandering the earth, I was 100 percent sure I wanted to work with Bill on whatever he wanted to do next.
I didn’t know the specifics of what was next until late, but I could’ve guessed that we were going to do a website, and who was going to migrate over from the old site, but that’s about all I knew. The reason I wanted to work there was because of Bill and Sean Fennessey and Chris Ryan and Juliet Litman and the people I really trusted.
On Bill Simmons
I owe a lot of my career to him, I’m grateful to him on that level. But he’s also the most fun and interesting guy to talk to about the stuff I write about. There’s almost nobody I want to talk to about the sports media more than Bill. He’s got his opinions, and he’s as rabid a consumer as anyone in the world. He’s been watching his whole life, he’s been reading his whole life. That’s the thing I think is so fun about him.
We’re relatively elderly on the Ringer time scale; we remember the world of newspapers. We have had very, very similar experiences with stuff we were reading and stuff we were writing.
On the Ringer
We try to make it as different from Grantland as we possibly can in a lot of ways. At the same time, I think the one thing that’s similar is that formula of picking writers you like and finding the best way for those writers to succeed on their own terms. That’s the formula. It’s just going to play out in a different way. I think that basic formula’s the same.
Editor-at-large, it’s a very old title. I think it used to be the out to pasture title for editors at Time, Inc. It’s having a voice in everything we do. I try to be a voice. I try to help out Bill and Sean as much as I can, in having a voice and enthusiasm. I just want to be there and give an opinion.
I’m incredibly happy, and I would tell you if I wasn’t. I’m completely happy, and I just want to do whatever I can do to help the Ringer succeed. That was like the most boring cliché you’ll ever get from an NBA player, but it’s true.
On how he evaluates success
I know this sounds like bull, but it’s almost all determined by whether I thought the piece was successful and whether I was happy with it the moment I sent it off.
Nobody knows how you reported the piece, and how you wrote it, and what went into all that. So, I could read a piece of journalism and say, ‘This was good,’ but the guy who wrote it could say, ‘You thought it was A-, but I had A+ material.’ For me, you have more knowledge about your own work so you basically know. That’s really it. I think as you get older that becomes more of a thing.
On the best and worst part of journalism today
I think the worst thing is the access to the athletes. Forget the stupid word access. I think the worst thing is the distance we have between the athletes and us. It’s funny because you look at this, it’s sort of like, ‘Oh, we used to joke around with the athletes and go out to drink with them.’
It was all about power, newspapers used to be powerful institutions. Back in those days, teams needed newspapers to disseminate information. When newspapers shrunk and the media shrunk, and athletes got richer, they don’t really need us anymore. It’s not that we did anything wrong, it’s just the world has changed and it’s not going to go back.
I love newspapers, and I love the old and current sports page. But I think the best thing to happen to sports writing is the fall of the constraints of the newspaper. It allows you to bring in topics that they wouldn’t have been able to bring in as frequently as the days of the newspaper. Have the sort of creative freedom that wasn’t granted by the newspaper. Having experienced and loved the former world, I love the new world a lot more.