Bill Simmons has always positioned himself as an outsider. It’s an odd sentiment given he made his fame at the most established brand in sports media, but Simmons has always envisioned himself as anti-establishment, even as he built an in-house empire and became an integral part of the machine known as ESPN.

On Friday TheNew York Timesbroke the news—the more accurate description is that ESPN president John Skipper and its management team picked a great venue and a well-respected reporter to deliver the news—that ESPN would not re-sign Simmons when his contract expires in September. ESPN later released a statement to Sports Illustrated and other media outlets.

"I decided today that we are not going to renew Bill Simmons' contract,” Skipper said in the statement. “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."

Multiple calls, emails and ravens to Simmons (and his reps) had not been returned as of this writing.

The timing of the news is surprising given that Skipper has repeatedly expressed his interest in retaining Simmons, and did so again last week on a Denison University sports radio show. In September, Skipper told this to SI.com: “My interest is high in re-signing Bill. We like Bill. He has done good work for us. We continue to have a good collaboration, and I am anxious to have some discussions with Bill to see if we can continue to do things that work for ESPN.”

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While the timing is surprising, it is not a shock that ESPN and Simmons are parting ways. While I think Skipper is fond of Simmons on a personal level and considers him a friend, I don't believe the frequency in which they discussed future plans is as great as the Times’s story indicates.

SI.com requested interviews with Skipper and Marie Donoghue, the company's exec vice president of global strategy and original content and the management staffer who works with Simmons on a day-to-day level at Grantland. ESPN declined those requests on Friday.

From the Simmons side: Simmons has been frustrated with parts of ESPN, including management, for some time. It’s been a slow burn, according to his friends. He was clearly dismayed by some of the projects he was involved in prior to this year, particularly on the television side. His experience on NBA Countdown was not a good one and his friends will tell you that he privately seethed last September when he was suspended by Skipper for three weeks after he called NFL commissioner Roger Goodell a "liar" (among other things) on his podcast, The B.S. Report, following Goodell’s press conference Sept. 19 on the league's ongoing domestic violence issues. Of significant importance, Simmons dared ESPN management to discipline him for those comments on the same podcast.

Bill Simmons, ESPN to part ways after contract expires in September

That three-week suspension (which included two weeks without pay) was two weeks longer than what Stephen A. Smith received when, in the midst of discussing the NFL’s adjudication of Ray Rice on "First Take," he suggested that women should examine their role in provoking domestic violence incidents. Smith was ultimately suspended for a week, but that came after Smith returned to the air to apologize and followed a p.r. statement that offered "a lot of discussion and reflection on the topic" but no adjudication. Suspensions have been doled out inconsistently for years at ESPN, and the process by which they were decided was convoluted (and slow). Simmons’s suspension was the new test case for speedier suspensions and, from what I understand, Simmons was furious about discipline that he believed was far harsher than what the crime warranted.

From the ESPN side: First, finances are always at play with decisions of this magnitude. One longtime ESPN staffer said Skipper’s decision was not surprising given the economic reality of two lagging quarters for ESPN and the salary Simmons would be seeking given his market value (likely in excess of $5 million per year).

“Grantland is an artistic success, but it is not close to making money,” said the ESPN insider. “That matters now more than ever in this new reality. Tough choices. Not to mention the personal history here, and his history of not playing nice in the sandbox. Seriously, the dude is talented, and his greatest legacy will be pushing 30 for 30, but he may shortly discover the power of this brand.”

Also, former executive editor John Walsh was the biggest buffer between Simmons and Bristol-based management and has long been his principal champion and rabbi. (Walsh hired him.) Walsh’s impact had been significantly reduced the last few years and once that happened the dynamic between Simmons and those back in Bristol changed. Simmons also alienated some producers and editors who disliked working with him. “Let’s just say the mood is festive,” said one Bristol-based staffer in response to the Simmons news.

Longtime ESPN chronicler James Andrew Miller, co-author of "Those Guys Have All The Fun" called Simmons's Thursday appearance on the Dan Patrick Show, in which he ripped Goodell for his handling of Deflategate, "a tipping point" between Simmons and the company.

The fallout: Multiple sources at ESPN confirmed that there will be no changes to ESPN’s documentary series 30 for 30, for which Simmons served as an executive producer. That department continues on as is with two dozens projects in the pipeline. (The head of ESPN Films, Connor Schell, declined to comment through ESPN p.r.)

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Despite going into lockdown mode today—multiple Grantland staffers who are usually accessible could not be reached for comment—the majority of the Grantland staff swear by Simmons and hold him responsible for the creative freedom and large salaries that they have. ESPN says Grantland will continue on—ESPN owns it—and the company in my opinion will extend it as long as possible in part to prove that it does not need Simmons to thrive. Grantland has long been a pet project for Skipper, and he publicly supported the site on Friday. “It long ago went from being a Bill Simmons site to one that can stand on its own,” Skipper told Sandomir today, pointedly.

While Grantland can surely stand on its own with its tremendous talent, Simmons remained the site’s major attraction when it came to metrics and external sales, including through ESPN’s upfronts. Also, on Friday, Peter Kafka of re/code reported that David Cho, who has been publisher of Grantland since the start in 2011, gave his notice to ESPN last week. On the issue of whether Simmons will continue to do podcasts and the rest of his regular work at Grantland, sources told SI.com not to presume he'll be on a permanent vacation prior to the conclusion of his contract.

What’s next? That’s the obvious question. One longtime agent who has worked with various networks placed Simmons's potential earnings at $7-10 million per year. “Look for him owning his dot-com rights and all the content that comes with it including podcasts,” said the agent. “And a TV play such as Turner, Fox, HBO or Showtime.”

How a college radio host landed an interview with ESPN's John Skipper

(Simmons is represented by James Dixon, whose talent roster includes Stephen Colbert, Carson Daly, Jimmy Kimmel, Jon Stewart and Adam Carolla. Dixon will get his client money.)

The possible suitors for Simmons include other traditional media companies, such as Fox Sports where one of Simmons’ longtime friends and admirers, Jamie Horowitz, just took a job as the president of Fox Sports National Networks. Horowitz will oversee programming, marketing and scheduling for Fox Sports 1 and Fox Sports 2 and supervise management and development of original programming.

(In September 2013, Simmons told SI.com: “Fox Sports 1 talked a big game before they launched and deserved a little ribbing. Remember, they were posing for magazine covers, trying to steal ESPN people, bragging about having ‘fun’ and taking veiled shots at us. Meanwhile, the NBA previews I did with Jalen [Rose] for Grantland Channel would be their highest-rated show right now. Why are we even talking about them, Deitsch? When they can come up with a show that can out-rate me and Jalen wearing the same clothes for six straight hours on YouTube, get back to me.”)

Turner Sports has the rights to the NBA, which is Simmons’ bailiwick, and a big digital property in Bleacher Report. “It’s premature to discuss at this time,” said a Turner Sports spokesperson on Friday.

Yahoo! could also be a factor given its scope and cash flow, though the site’s sports impact has lessened with some talent departure. As Sandomir wrote, Simmons could use his high profile to start his own multimedia platform with investment from private equity.

I’ve known Simmons a long time and I imagine he won’t say much in the near-term. But rest assured, he will be motivated to build something that takes on his old employer in some arena. His story at ESPN in essence ends today, but another one is just beginning.