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Peter Kafka of re/code recently caught up with Simmons at SXSW in Austin and spoke to the artist formerly known as "The Sports Guy" about his future.
Simmons says that his decision on whether or not to stay at ESPN will start with how they plan to handle his website, Grantland.com, moving forward, noting that right now he thinks "they take it for granted."
"I just think Grantland's at a crucial point now where we're doing the site that we have now really, really well," Simmons told re/code. "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 stay the same, it's going to stagnate a little bit."
While Simmons says he has not made any demands to ESPN about Grantland, he does make it clear that changes need to be made and it sounds like his next move may be his last in terms of what he is doing now.
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Simmons reportedly makes more than $5 million per year at ESPN, but the relationship has been rocky in recent years.
During his interview with re/code, Simmons said he hasn't had a lot of contact with ESPN President John Skipper or others in charge at ESPN "since last September."
This is almost certainly a reference to his suspension last September when he went on a rant against NFL Commissioner Roger Goodell and dared ESPN to suspend him.
Simmons concedes that part of the problem is that Grantland is such a small piece of ESPN's pie that they may not feel it is worth the effort, noting that ESPN makes "billions of dollars with TV rights." However he also says ESPN has a "responsibility" to continue to push successful side projects they "dabble in" to see how great they can be.
On the flip side, ESPN's outgoing ombudsman, Robert Lipsyte, recently explained in an interview with TheBigLead.com that ESPN doesn't need Simmons to continue nurturing side projects like Grantland or the "30 for 30" documentaries.
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Yes, ESPN can keep those going and the content in all likelihood would be just as great or even continue to get better.
However, ESPN's problem is two-fold: 1) What's next? Simmons didn't invent sports documentaries or multimedia websites but he helped bring them to ESPN in a great way. ESPN has them now, but who is going to come up with the next great idea?; and 2) Who is going to be the central personality to bring the masses to those endeavors? Love him or hate, Simmons is a personality that people gravitate towards.
ESPN will be fine if Simmons leaves but it wouldn't be the same.
Business Insider reached out to ESPN for comment and will update this post if we hear back.