Bill Simmons and the World Wide Leader are headed for a split after an almost 15-year marriage. ESPN president John Skipper announced the network would not be renewing Simmons's contract after the two sides failed to reach an agreement on an extension. With Simmons set to hit unemployment, the biggest question is what's next. Could NBA TV or TNT be in his future?

Simmons and ESPN have always had a somewhat contentious relationship, but it was one that they both benefited from. After close to 15 years together, though, the two sides are ready to go different ways.

"I've decided that I'm not going to renew his contract," Skipper told the New York Times, in an article published Friday morning. "We've been talking to Bill and his agent and it was clear we weren't going to get to the terms so we were better off focusing on transition."

Skipper said the reason why the network and Simmons failed to reach an extension was "about more than money," suggesting there were bigger differences that the two sides were unwilling to compromise on.

In their almost two decades together, ESPN and Simmons frequently butted heads - mostly over creative freedom and the ability for him to criticize whatever or whomever he wanted, including his own employer . The latter point of contention - Simmons's outspokenness - earned him a number of reprimands over the years from ESPN.  He was suspended from Twitter on two different occasions, the first for criticizing a radio station and the second for criticizing the ESPN show "First Take." More recently, he was suspended three weeks from the network for violating the company's "journalistic standards" after he criticized NFL commissioner Roger Goodell and dared ESPN discipline him.

Skipper indicated the Goodell incident didn't factor into his decision not to renew Simmons's contract. Coincidentally, Skipper's announcement about dropping Simmons came a day after Simmons again spoke publicly about Goodell.

As for Grantland, Simmons's flagship website that operates under the ESPN banner, Skipper said it would be unaffected by the change. "It long ago went from being a Bill Simmons site to one that can stand on its own," he said.

Simmons will be unemployed for however long he wants. He's become a household name in the sports world - thanks to Grantland, his podcasts, his on-air commentating and his "30 for 30" documentary film series - and will have companies knocking at his door, likely with the promise of total creative freedom.

NBA TV* and TNT, the only other two networks that broadcast professional games, could be possibilities if Simmons wants to maintain a television presence in the basketball world. NBA TV needs a name with star-power to boost its profile, given how sorely lacking the network is in big-name analysts and commentators. TNT has an incredible stable of on-air talents, and it's unlikely to fiddle with the amazing chemistry of its team. But, then again, the idea of teaming Simmons with the likes of Charles Barkley and Shaq could be too tempting to resist.

Signing with a media outlet like Fox or Yahoo Sports is also a possibility, as is creating his own digital platform by making another site like Grantland.

Simmons's contract expires at the end of September, according to the Washington Post. It's uncertain when and how ESPN will begin to transition him out of the company.

UPDATE (12:15 p.m. ET) - More from Skipper on his decision, via a statement ESPN emailed to the Washington Post's Erik Wemple:

"I decided today that we are not going to renew Bill Simmons' contract. We have been in negotiations and it was clear it was time to move on. ESPN's relationship with Bill has been mutually beneficial - he has produced great content for us for many years and ESPN has provided him many new opportunities to spread his wings. We wish Bill continued success as he plans his next chapter. ESPN remains committed to Grantland and we have a strong team in place."

*NBA TV is owned by the league but operated by Turner, which owns TNT and Bleacher Report.