Deadspin: An Oral History

How an irreverent sports site made the big leagues

It all goes back to Ron Mexico.

In 2005, The Smoking Gun broke the story of a legal complaint about a prominent athlete who “knowingly failed to advise” a partner that he was infected with a sexually transmitted disease. The athlete, then-phenom Michael Vick, was reported to have used the alias Ron Mexico during herpes testing, a story that quickly spread across the nascent blog culture of the Internet.

Will Leitch, an early, struggling blogger, got the idea for Deadspin after taking note of what he believed to be a failure in mainstream sports media: It wasn’t covering or even mentioning stories like the tale of Ron Mexico—stories that sports fans were eating up. Partnering with Nick Denton’s Gawker Media, Leitch launched a site that would talk to the average sports fan like a real average sports fan, eschewing, as the site’s motto goes, “access, favor and discretion.”

Over the last seven years, Deadspin has grown from a one-man operation run out of a bedroom into a formidable counterweight to the sports media industrial complex of Sports Illustrated, ESPN and other players. Along the way, Leitch and successive editors have exposed star athletes and top media personalities, offended countless readers and managed to make over the culture of sports journalism, all from the outside.

On Jan. 16, the site was the first news outlet to report that Notre Dame linebacker Manti Te'o’s girlfriend, whose “death” was the basis of one of the more inspiring stories of the past year, was a complete hoax. The story would explode and cement Deadspin’s place at the head table of the sports media world—and the mainstream media’s worst nightmare.

‘Sports Needs a Wonkette’

Lockhart Steele, managing editor, Gawker Media (2005-’07): Will [Leitch, Deadspin’s founder and its editor from 2005 to 2008] was pondering a sports site and asked to submit a pitch to Nick and me. Nick said he loved him, so Leitch wrote a memo, which was excellent, and it convinced us that we should do a Gawker sports blog.

Photo: Chester Higgins Jr/The New York Times/Redux

Excerpt from Leitch’s original pitch to Denton: “The Internet and sports are made for each other. But what has really been missing has been a strong, askew voice from outside the circle jerk of buffet-addled sportswriters interviewing naked athletes. Independent sports blogs are everywhere, but they don’t have any passion. They’re mostly just stat nerds. Sports needs a Wonkette, essentially.”

Leitch: Lock was sold enough that they thought they should do a sports site, but they didn’t want me—they wanted a name. I know a friend of mine was asked and turned it down because he thought ESPN was a safer bet and better money. Lockhart sent me an email that said, “Bad news. Nobody wants to do this. But the good news is, it’s your site now.” I was told I’d have six months to try and make it work, and I thought, that’s fine. I had been answering phones at a doctor’s office only a year and a half before.

Nick Denton, founder and publisher, Gawker Media: I don’t remember ever wanting Will to do another kind of site, but I think I had some hesitation over the breadth of coverage required. I wasn’t really clear that there were sports fans per se—rather, that there were fans of particular sports and particular teams. So I wasn’t sure it was a homogenous enough topic to support a broad site.


Naming Deadspin

During the arduous naming process, multiple names were bandied about, including Miscaster, Deadball, Offscore, Offjock, Spinstop, Tronball and finally Deadspin.

Transcript of AIM chat, June 6, 2005:

mynameisleitch: Hmm. Deadspin. That’s not horrible. Is that the general consensus?

lockhart steele: it was the favorite of the group yesterday

mynameisleitch: It’s no Tronball, that’s for sure.

mynameisleitch: Deadball is almost better.

mynameisleitch: But deadspin is not bad.

lockhart steele: i like it

lockhart steele: perhaps more importantly, Mr. Denton likes it

mynameisleitch: Yes. It’s livable.

lockhart steele: ponder it. let it roll off the tongue.

Steele: Nick has a brilliant way with [naming sites]. They were never cutesy; they always had a negative vibe or a dark edge. It was a fairly contentious back-and-forth until Denton, huddled alone one day, came up with Deadspin. It’s a wonderful irony that one of the most popular sports blogs in the world was named by a gay Brit who hates sports.

Building Steam

It didn’t take long for Leitch and Co. to break into the blogosphere, but the site’s crossover into popular culture was a turning point. Leitch and Deadspin writer Rick Chandler gained notoriety publishing embarrassing ESPN anecdotes and photos of athletes that would go viral, like the shot of then-Chicago Bears quarterback Kyle Orton drunk at a party.

Rick Chandler, Deadspin writer, 2005-’09: Before long, we kind of realized we were able to do things mainstream media wasn’t able to do. There were a couple posts that became really popular. When I did this story about [ESPN anchor] Chris Berman stealing a guy’s girlfriend in a bar—it became known as “You’re with me, leather”—I wrote the post thinking it’d be a typical item, and it just blew up and grew into popular culture. There was a reference to it on the TV show Las Vegas, and I just thought, oh my God. I realized then we had something pretty big on our hands.

Steele: “You’re with me, leather” is kind of the “Oh, shit” moment. That’s when you realized Deadspin could hit into pop culture and go viral, and that’s when it came into its own.

Richard Deitsch, senior editor/media writer, Sports Illustrated: I did a fellowship at the University of Michigan in 2008, and I would talk to student after student and Deadspin would come up more than anything else. They’d link Deadspin to Sports Illustrated or their local paper, and they didn’t distinguish it as anything other than part of their normal reading diet. It was just another place they’d go to for news. I thought, man, we’re in a new ballgame.

Leitch: Neil Best from Newsday wrote what I think was the first thing about the site and called it the insider’s sports blog. And I read that and thought, dude, it’s literally me in my room over here. What I was doing was the opposite of insider.

First big hit was when we had the pictures of Kyle Orton clearly drunk at a party. A reader sent them over, and back then there was none of that faux outrage or concern trolling that is so common now on the Internet. It was like, hey, here’s a funny picture! The only people then that cared weren’t the athletes but the people who handle the athletes and had money at stake with their reputations. Nobody thought I was a smut peddler or I was out to get anybody. There was an innocent silliness to it.

I feel like one of the reasons Deadspin got tagged with this label of being dangerous is because right around this time people at newspapers were starting to lose their jobs. I feel like that was around the time where newspapers were starting to struggle and they needed a villain, and here’s a guy who is putting up pictures of drunk athletes.

Tommy Craggs, editor in chief, Deadspin (2011-present): I remember A.J. [Daulerio, editor in chief, Deadspin, 2008-’11; editor in chief, Gawker, 2011-’13] told me about the Josh Hamilton photos and asked me what I thought of it and I had reservations. [In August 2009, Deadspin published photos of the Texas Rangers’ Josh Hamilton, shirtless and drunk at a bar. Hamilton has struggled with drug and alcohol addiction and the photos were regarded as proof of a relapse.] I was caught up in “Why should we hold Josh to a higher standard than ourselves here?” This was the cautious, j-school superego in me. Now I have no qualms about the story at all. Before [Brett] Favre [who, in October 2010, was caught texting photos of his privates, a story Deadspin broke], it was the story that put [us] on the map. It kind of announced us as dirtbags but in a different way. You know, a site dedicated to telling the unauthorized version.

Those Pesky Commenters

All sports sites have lively comment communities. But Deadspin's are special.

Steele: A real turning point for Deadspin came when we launched comments. At launch we didn’t have them. Nobody was more against the idea of comments than Will. Eventually, I had to tell him, “This is non-negotiable.”  We had no idea that it would be one of the most robust parts of the site. The quality of those who met in the comments section was wild. It was one of the great hilarities of Deadspin.

Leitch: I didn't want comments at all. This was my little play land. I was having too much fun and comments added a new element. I didn't know or even care if people were reading Deadspin at the time. I was just enjoying sitting in my little room. I had stopped looking at traffic. I said, “Just tell me at the end of each month if I don't get my traffic goals. Just give me one warning and if I screw up again you can fire me.” I’m still like that now and I just don't want to know the numbers. Chasing the traffic demon is the end of it all. I think it's made everything [online] stupid.

Magary: He'd seen how bad comments were on other sites. Most commenters on Yahoo and ESPN are morons writing things that are breathtakingly stupid. He probably thought, “Okay, I'll write something smart, then commenters will call the President Hitler and this will suck.”

There was one point early on where Will would pull out comments of mine and stick them in a post and when he did that I'd be like, “Oh my God! Leitch posted the comment! I don't feel so alone anymore! I’m so happy!” Five of us commenters eventually started a site called Kissing Suzy Kolber and Will championed our cause early. Every time he'd email me I’d get excited and think, “Wow a big media person likes our stuff.” 

Leitch: I got over the comments issue quick because Deadspin commenters ended up being so awesome. It ended up that I worked the top part of the site and they worked the bottom. I never really read comments then, though I didn’t have any problems with them. After a while, I realized “Oh, its actually really funny!” By the time it had become a community though I was too busy writing posts. The Deadspin community formed entirely outside of my doing. I didn't foster it. Not that I didn’t want it, but I just had no time to do it.

A unique relationship with ESPN

Denton: What decided me on Deadspin was the existence of a clear enemy. It was arranged not so much around one singular passion as one singular jihad against the cozy cartel of ESPN and the managers.

Leitch: At the time, nobody wanted to rip on ESPN because they thought at some point they were going to have to work for them. Now, as somebody uninterested in a career as a sports reporter, I was free not to worry about that. I think in the early days it was thought of as this cute, funny, “I can’t believe they’re getting away with this” kind of thing.

Drew Magary, Deadspin commenter turned columnist, 2005-present: A lot of frustration came from the idea that ESPN changed for the worse, especially being bought by Disney. For a lot of us, it was the inevitable consequence of massive growth where nobody could help it from metastasizing into a company that exists to feed itself.

Deitsch: The writing was always very good, and even though there were things I didn’t particularly like, there was clear intellect behind it. I remember thinking that ESPN is in trouble if they don’t consider these guys a factor. They’re smart. It has been interesting to watch the relationship evolve. If Leitch had an uneasy alliance with ESPN, then Daulerio went Death Star on them.

Daulerio: When I took over for Will, I established a rapport with people who worked at ESPN and the PR guys, and I said, “If you want to be in my imaginary gold club, you could get this right of first refusal or comment on any stories about you in exchange for other information.” For the most part, I was trying to play by standard journalistic practices. It was a pretty solid and fair relationship in my mind. There was so much out there we saw that went unreported by us.

Deitsch: I think it’s interesting that Deadspin developed a huge sourcing network at ESPN with near daily interaction between Deadspin and ESPN-ers. I think some at ESPN like that there is a site out there that is constantly involved and always checking them.

Denton: (On ESPN’s sources) Deadspin’s biggest allies have been all those frustrated sports reporters whose journalistic ids were struggling for expression.


The Costas Incident

On April 29, 2008, Leitch appeared on the HBO show Costas Now in what was billed to be a conversation about blog culture and its effect on mainstream media. To Leitch’s surprise, the segment immediately went viral after a meltdown by Pulitzer Prize-winning sports writer Buzz Bissinger, who, in voicing his annoyance of blogging, showed visible disdain for Leitch, who Bissinger called “Jimmy Olsen on Percocet.”

Leitch: I’ve never watched that, by the way. I hate everything about that night. I wasn’t personally humiliated. I think Buzz Bissinger is a beautiful author and reporter, and it’s like that night broke him. The show turned it into this freak-show TV moment. Buzz has embraced this angry-guy persona now, and I think that has made him a worse writer. I think the reason it backfired for [Bissinger and Costas] is because they didn’t read the site or really know who I was. It’s like they thought I’d show up in a leather jacket looking like Johnny Rotten saying, “Fuck you and your media.” I found that night made everybody involved look dumb. I feel like it foretold how things were going to go. People didn’t care about an actual discussion.

Blowing Up Deadspin

In the summer of 2008, Leitch left Deadspin for New York magazine, with A.J. Daulerio taking over as editor in chief. Quickly making his mark, he revamped Deadspin’s reader comments, focused on more magazine-style reporting and ratcheted up his war with the sports media establishment.

Leitch: I had to really fight to get Denton to give him the job. A.J. famously told him he’d give him his left nut for the job.

Denton: I can never remember whether it was left ball or right ball actually, but the ball speech convinced me [to promote A.J.]. Conviction is a rare commodity.

Daulerio: Tommy and I established the formula that we’d try to do more and not just treat this thing like a blog—small-scale, original reporting, fun stuff, aggregation—and build it into a different direction. People didn’t notice that alongside some of the Favre-type stories, we would have this magazine content you’d expect to find on Slate or something.

Other Gawker sites were doing 60 posts a day, and we’d do, like, eight. But we’d get, like, one post a month where we’d get all these uniques and we were going outside our readership. We alienated a lot of Deadspin’s core audience, but it felt like the natural thing to do. I was looking to do my own thing, and there was a bigger world out there.

Leitch: The first thing A.J. said when he took over the site is, “I just don’t want to kill this.” If A.J. had run Deadspin the old way I did, the site would’ve died. He did some stuff that I disagreed with and disagree with now. It’s probably good that I got out when I did. Deadspin was my absolute life, but nothing like that can last. Eventually it had to get bigger. It needed to become more gossipy and there is nothing wrong with that, but it wasn’t something I cared to do.

Chandler: Everything changed. I always looked at it as our passion project, and we were outsiders not beholden to corporate interests or anything. Then when Will left, Deadspin became what we were mocking. We became big. We were on a level, kind of, with ESPN and the mainstream. It was disappointing to me, but inevitable. That’s the direction they wanted to go. They went that way, and it wasn’t something I felt I wanted to be a part of anymore.

Craggs: A.J. took an omni-directional approach to covering ESPN. He would look for any way to fuck with them that he could think of. I wasn’t totally thrilled about the “horndoggery” stuff [one of Deadspin’s ongoing initiatives to root out rampant sexual behavior among ESPN staffers and executives]. As a stunt, it was awesome. As a way of attacking ESPN, it wasn’t my favorite piece of ESPN. It sort of made Deadspin look anti-sex, and we’re certainly not anti-wanton-sex. That was part of the philosophy of any weapon at hand.

Favre as the White Whale

Before Manti Te'o, Deadspin’s biggest moment was when it broke the news that then-New York Jets quarterback Brett Favre had left a series of inappropriate voicemails and pictures on the phone of sideline reporter Jenn Sterger. Deadspin published the pictures and emails, taking heat for the decision at the same time it found itself at the forefront of a major national news story.

Leitch: Favre is the story that really broke Deadspin. Now, I’m not ashamed of anything A.J. has ever done on with the site—I will say I would have never gotten the Favre story, but because I wouldn’t have cared enough personally to pursue it. People don’t realize that A.J. went out and got that story. He chased it for a very long time.

Deitsch: A.J. pushed the envelope. I don’t think any mainstream publication would put the Favre story up. What A.J.’s Deadspin did was it allowed a lot of mainstream publications to do follow-ups on stories they normally wouldn’t do. There’s no way the New York Post would run Favre junk photos, but they could do a follow-up 10 seconds after Deadspin released the photos. Deadspin took pressure off the mainstream to cover stories that would get pageviews.

Magary: The Favre shots put Deadspin in the rotation of big sites on par with the bigger sites and in the same breath as places like ESPN as far as sports news and opinion. It legitimized the site, which is funny thing considering it came from dick pics. A.J. actually told me about the Favre photos before he posted them, and I have a huge mouth and blurt things out all the time. I promised I wouldn’t tell, and I was writing the NFL column that week and it was supposed to run after the Favre post so I mentioned what we had, but I accidentally hit publish instead of save as draft. He paid 10 grand for that, and I spoiled it. He was so pissed.

Daulerio: I went to Craggs and said, “Man, I think this is the white whale.” From February until August, I asked who knew about this and ESPN knew as well. They felt it was insignificant and asked why I’d want to run this. I could not for the life of me understand why people shouldn’t know about this. Finally, I figured I’d pull the trigger. I called Jenn [Sterger], and she said to wait. I didn’t want her to change the whole piece, so I figured I’d go with the information I had and take the risk that somebody else out there would have this or back me up. It was a make or break moment. If it didn’t pan out, it would be a “look what horrible human beings these guys are” thing.

Two weeks later, I got an anonymous email about some pictures. The guy wouldn’t tell me how he knew Jenn. He wanted $20,000, and I got it down to $10,000 plus travel expenses. Next thing I know, everything I’d chased was there sitting on a little disc. We spent the whole night packaging it, and I actually didn’t want to go with the Favre photos. There was nothing that shows people it is him. We crosschecked the phone numbers and knew it was him, but I knew everyone would focus too much on the photo. Tommy convinced me to go with the dick photo.

Denton: I think it was A.J. who was against the Favre dick, funnily enough, and Craggs who was pro.

Daulerio: When Favre was asked at a press conference later about the photos and Favre waved it off, that’s when I thought, I got it. Slowly but surely, all the NFL beat reporters came out of the woodwork and said, “I don’t support how you got this, but you are right.” It was surreal for me. I hated the fact that people didn’t realize that the actual photo isn’t the whole story. The story is about the scummy nature of what he did and the possibility that there was harassment going on, as well as the idea that this kind of thing is accepted behavior in the NFL.

Coming full circle: the Te’o story

In late November 2011, Daulerio left Deadspin to assume editorship of Gawker Media’s flagship property, Gawker, placing senior editor Tommy Craggs at the helm.

Leitch: Craggs found the strike zone between the two of us. There is this high-minded great work out there, but it’s supplemented with the big traffic hits.

Craggs: A.J. and I have different temperaments.

Daulerio: The Te’o story was Tommy’s doing, and he took it to this level way past Favre. They’re on a new level now. This is, in a lot of ways, the perfect Deadspin story and shows that mainstream media isn’t quite caught up if they’re missing stories of this magnitude, and we showed them we could rise up and do it. This will last them for a while. Deadspin becomes part of the story, too, because they aren’t that well-known. It couldn’t have worked out better.

Craggs: The great thing about the Te’o story is that it is everything the site has been built toward since it was founded. There’s always this idea that under A.J. the site swerved dramatically in a different direction, but the soul of the site has always been the same. The only thing that changed was the style. You’ve created a self-conscious alternative to the mainstream media. What changes is maybe a few doors that weren’t open before when we were “the penis site,” maybe those open now. Maybe more people see us as a place to get the unauthorized version of the story. I don’t think anything changes about the trajectory of the site, though.

Strip Club photos: courtesy of Deadspin