The subject of the 2013 debut of the Weekend Interview is Charlie Warzel. After we featured his recent piece for Adweek’s Sports Issue, “Deadspin: An Oral History: How an irreverent sports site made the big leagues” earlier this week, Charlie graciously agreed to share his behind-the-scenes experiences and thoughts regarding the article and the state of online sports media.

Be sure to read the article, which opens with, “It all goes back to Ron Mexico,” and closes with, “Strip Club photos: courtesy of Deadspin.” Then check out our conversation, below.

AD: What’s your role at Adweek? How did you all decide to do a “Sports Issue”?

CW: I’m officially billed as ‘Staff Writer’ but probably the more apt term would be Digital Media Reporter. I cover the online publishing industry (websites, advertising!) and spend a bit of time in the web culture realm (memes, etc!) and I’m always trying to look at how media as a whole is evolving from content and business perspectives. As far as the Sports Issue, it’s now an annual issue Adweek does on the heels of the Super Bowl (you know, because of all the ads).

AD: Was it obvious that Deadspin needed to be a part of that? 

CW: I have been a casual Deadspin reader for a while so I’ve watched as the site has evolved. I’ve read a few of [Deadspin founder and first editor-in-chief] Will Leitch’s books too, including God Save The Fan, which has a good bit of Deadspin lore baked into it. One of my colleagues ran a feature alongside mine profiling ESPN honcho John Skipper, so when I suggested something on Deadspin, the editors decided it would be a nice balance for the issue.

AD: Did their breaking of the Manti Te’o story factor into the decision to include them?

CW: Oddly enough, I pitched this story in December of last year and got the green light to do the piece right before Christmas. I started working on the piece in early January before even Deadspin knew T’eo’s girlfriend was fake.

The day the T’eo story broke was the day I sat down with Will. It happened during our nearly two-hour interview. Neither of us were checking our phones. Since oral histories are rarely done for things that are still around, Will joked that I’d probably miss Deadspin’s biggest story by two weeks. I didn’t see the T’eo story until I left the interview but it was pretty unreal timing. It certainly lit a fire under my ass to get the piece done. In the end though, the timing was just an unbelievable coincidence.

AD: How did you come to be the one who put together the Deadspin piece? Why an oral history?

CW: It was mine since I pitched it. I pitched it as an oral history partially because I’d never written one and wanted to take a crack at the format, but also because there are a lot of people involved in the site’s history and I wanted it to be comprehensive.

AD: In putting it together, did you conduct a series of one-on-one interviews, or did you talk to folks together, in groupings? In person, or by phone or email?

CW: It was all one-on-one interviews. Pretty much did [it] by any means necessary: sit downs, phone calls, emails, and IMs. Though the vast majority were sit down and phone conversations. Lots and lots of transcription though. It came out to like 47 pages or something when I tallied it all up.

AD: Were there any people you wanted to interview for the article who refused to talk to you?

CW: Yeah. Everyone from Gawker Media and Deadspin was very cooperative. Had some prominent outside voices in the sports media world that I approached who either passed or didn’t respond. Won’t name names, but you might be able to guess one or two…

AD: Because of the article’s styling as an oral history, you don’t really get to say a lot, save for the introduction. If you were writing a more traditional profile, what observations of the main subjects– editors-in-chief Will Leitch, A.J. Daulerio, and Tommy Craggs– would you have included? How much Molson Stock did you feed them during the interviews?

CW: Man, I don’t know. Will has been profiled a bit back in the day and Gabriel Sherman did an interesting profile of Daulerio at GQ a while back. It would have been fun to play with a narrative, but it would’ve been too long. I only have one regret with the piece: I wish I could’ve included more anecdotes, etc. But you read a lot of these oral histories and they’re just epics. For print I only had 3000 words. I brought it near 4000 for online though.

A true gentleman never discusses his Molson count.

AD: How important do you think it was to Deadspin’s success that the site was part of the Gawker Media Group from day one?

CW: The Gawker Media platform had to have been helpful for Will, but I think he very quickly made his own name and I think it existed apart from the Gawker name in a way that most other Gawker blogs didn’t. The key thing was probably that they paid Will to do it. Sounds silly now, but at the time I think he was one of the only paid sports bloggers. They allowed it to be a full time job and I think that makes all the difference.

AD: In the wake of the Te’o story, and particularly with the revelation that ESPN had been sitting on the story for days, there was some suggestion kicking around the web, including from former Deadspin editor Clay Travis, that a) institutional media networks don’t like to break controversial stories like this, but that b) they like and even aid an outlet like Deadspin in breaking the story so that the network can c) scoop up eyeballs by reacting to a story that’s already “a story” d) without taking any risks themselves (basically Leitch’s hobbyhorse motif about “access”). 1) Do you think that dynamic exists, whether with respect to the Te’o story or in general? and, if so, 2) why do you think Deadspin is well-situated to handle that role? Is that a position you think they want to maintain? Should maintain?

CW: Absolutely, it exists. Take ESPN, which broadcasts tons of games and has to deal with broadcast rights and the leagues. ESPN’s business side is complex and unfortunately, that can have an impact on [the editorial side]. It’s not always the end of the world, but when you look at Deadspin, which has the unique blend of cache (though absolutely nowhere near ESPN’s) and no outside entities to please, they are in a pretty solid spot. It’s nothing new, really. Deadspin has always been the place to break controversial stories, which allows other organizations to then touch the story and report on Deadspin’s reporting.

AD: Pontificating on the end of newspapers, paid reporters, and Real Journalism is old hat, but how important do you think these traditional journalism principles are to the Deadspin folks, given that the subject is entertainment?

CW: I think the “without access” portion of Deadspin’s motto is probably forever ingrained in the site’s DNA. I think since A.J. took over, reporting and “traditional journalism” are critical elements to the site. Not to say they won’t still have fun but Craggs is a j-school grad and the majority of Deadspin’s writers have really impressive journalistic backgrounds. Sure, Deadspin is entertainment, but all sports is entertainment. I think the T’eo story shows they’re an important counterweight to the ESPN’s of the world. They can report out and run the stories that others are afraid to. They’re in a pretty good spot with regard to that. We’ll see what they do with it.

AD: Craggs always has struck me as the best writer of the lot, and also as the most introspective, but the latter is conjecture based on the fact that he’s neither as civilly disobedient as Daulerio nor as out-and-about generally as Leitch. First, do you think that’s an accurate impression, and second, how do you think he’ll be able to walk the line between Deadspin-as-thoughtful, independent counterweight and Deadspin-as-TMZ Sportz?

CW: The similarities and differences of the three editors was the most interesting part of this whole process, I thought. Everyone I spoke to agreed with the characterization of Craggs as the best, most cerebral writer of the lot, with AJ, as the shitkicker. Will often referred to Deadspin like an “art project” of sorts, but unsustainable. A.J. came along and really reinvented it, focusing much more on reporting and adding a magazine-style component to it alongside the more incendiary stories. AJ’s Deadspin was pretty intrepid, he chased that Favre story for months and months before pulling the trigger and publishing. It seems Tommy was instrumental in helping A.J. reinvent Deadspin and he’s since found the best of all worlds. They’re still relentless with ESPN, but in a much more sophisticated way. By that, I mean a lot of reporting and well-placed criticism, rather than publishing cock shots. I don’t think you even have to ask if Tommy can walk the line, [the T’eo story] seems to me to be the proof of what Deadspin can do under his leadership. I bet we’ll see more of the same under a marginally larger staff.

AD: Daulerio left the EIC position at Deadspin to fill the same role at Gawker, and now, after a year at Gawker, he apparently is out on the streets. Did you get any sense of where he’ll land?

CW: You’d have to ask A.J. Hopefully, though, it’s clear in the piece that, regardless of what you might think of his methods, he’s a true reporter who is incredibly skilled at building  dynamic, successful web journalism of that Gawker media variety. He really changed and grew both Deadspin and Gawker, and I very highly doubt we’ve heard the last of him.

Thanks to Cuffie from Delaware for his role in making this interview possible.