If you were writing a Sports Media Trade Value column, where would you rank “Bill Simmons’ Expiring Contract”? Unlike many of the players The Sports Guy has typically applied that moniker to, Simmons himself seems to have plenty of value thanks to what he’s accomplished over the years, and his impending free agency could spark a bidding war if he doesn’t re-up with ESPN. The chances of him remaining with the Worldwide Leader are still very much there, but they appear to be declining; Simmons’ comments to Re/code’s Peter Kafka at SXSW this weekend seem to illustrate that. First, consider what he said about Grantland:

I think the thing that gets us the most excited is just pushing, and seeing how many things we can do, and how the site can keep growing. It’s a pivotal time for the site. At some point we’ve got to either start growing, or we have to figure out what’s going to happen.

Kafka then brings up his expiring contract, and asks Simmons if he could recreate Grantland elsewhere. Here’s Simmons’ response:

I don’t like the word “recreate.” That doesn’t make a lot of sense to me. Grantland has been the most important thing I’ve done now for five years. Everything I’ve done for the last five years has been geared toward the site. I think it’s a business. The frustrating thing is you have to keep growing to have a business. You can’t just say “Okay — we’re good, after three years — we don’t need more people.”

I just think Grantland’s at a crucial point now where we’re doing the site that we have now really, really well. And that’s been the case now for about 14 months. So now the question is, what does that mean to ESPN? I don’t know. I don’t know that it’s a me decision — it’s what does ESPN want from this site? Because if they just want it to say the same, it’s going to stagnate a little bit.

That, plus Simmons’ further comments about the “responsibility” ESPN has to decide how to further grow Grantland, looks like some frustration with the resources he has. However, that may all be part of a contract negotiation plan. (Negotiating through the media? This is becoming more and more of a typical sports saga.) What’s perhaps even more fascinating are Simmons’ comments about the lack of contact he’s had with top ESPN executives since his September suspension for calling Roger Goodell a liar. Here’s the back-and-forth he had with Kafka about that (Kafka’s comments are in bold):

But you’ve made some suggestions, presumably, to [ESPN head] John Skipper and those folks.

No, I haven’t, actually. I haven’t had a lot of contact with those people since last September.

That was the Goodell thing. Does that experience influence your decision?

I don’t know. What I care about is the people I work with. Those are the people who know how much time we’ve put into everything. And we’ve never had … we’ve always been understaffed, always. We’ve had to pick certain people who are just overachieving, people that care about the product that we have. And, you know — at some point you want to have the right number of people, you want to start adding verticals and certain things. And if you’re not prepared to do that, I don’t know what’s left.

So that conversation has to happen first. And then you have to have a conversation afterward about me, and what I want to do. I still feel like I have five years left, where I can work at this pace. In five years I’m going to be 50, and I don’t know how hard I’m going to be able to work. I know how hard I work now. I don’t know if it’s going to be sustainable.

I think they take it for granted. Not just how hard I work, but how hard everybody works.

Yeah, none of that sounds like someone who’s ecstatic about signing a new deal with ESPN. The Worldwide Leader doesn’t seem to be moving heaven and earth to retain Simmons, either; it’s interesting that ESPN president John Skipper said he was “anxious to have some discussions” with Simmons about a contract back in mid-February, but almost a month later, Simmons still hasn’t talked to Skipper. That could be some negotiation through the media on the other side of the fence, but it’s worth noting that ESPN certainly doesn’t seem to be trying to alleviate Simmons’ concerns. At least they have been a little more tolerant of him recently, with no suspensions forthcoming for stunts like calling Mike and Mike “absolute garbage” and mocking his suspension on his podcast. Still, if one of your highest-profile employees is about to become a free agent, doesn’t it make sense to at least reach out to him with the equivalent of a qualifying offer?

It’s too soon to write the “Bill Simmons has left ESPN” stories. While there will be plenty of outlets bidding if he does reach free agency, networks will be at an overall profile disadvantage against ESPN, established online outlets won’t be able to offer as much of a TV presence, and creating his own startup may seem less appealing in the wake of impressive sites like GigaOm going under. Simmons’ profile gives him an edge over just about any sportswriter, but it’s extremely difficult to make any sort of news-based startup work these days. If ESPN decides they want to make a strong offer to keep Simmons, their resources and their multimedia presence may give them an edge. This interview suggests relations between the sides aren’t all that good, though, and ESPN’s chances of retaining Simmons are looking lower than they have been. We’ll see if the bosses can patch things up, or if the Sports Guy will be taking his talents to another destination.


About Andrew Bucholtz

Andrew Bucholtz has been covering sports media for Awful Announcing since 2012. He is also a staff writer for The Comeback. His previous work includes time at Yahoo! Sports Canada and Black Press.

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