Well hello again my faithful Chirp City compatriots, I have returned from my hiatus to impart wisdom and mostly just opinion on the cold dark world. I’d love to tell you I’ve been doing something other than consuming “Entourage” like it was crack cocaine, but with 81 episodes down in the last three weeks I’d say I still have the metaphorical white powder residue on my upper lip that’s kind of hard to explain. It’s not an addiction I swear I just have to get through the whole thing before the greatest fake-movie-star-group of all time makes their way to the big screen (best movie of the summer calling it right now).

However I was jolted out of my HBO-induced slumber when this morning I learned the news that ESPN will not renew Bill Simmons’ contract which expires in September. Here’s an excerpt from this New York Times article.

“I’ve decided that I’m not going to renew his contract,” John Skipper, the president of ESPN, said in a telephone interview. “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 that he made his decision to part ways with Simmons about three weeks ago.

Skipper said the differences between the company and Simmons were “about more than money,” although he would not offer details.

If you’re a sports fan, you either love or hate Simmons. He embraces being the most polarizing personality on ESPN, and makes no effort to hide his fanaticism for Boston sports teams, or his opinions on how things can be run better, which rubs some people the wrong way.

However, it’s very hard to read John Skipper’s comments without seeing it as a very personal problem between the two men. It’s funny to me that every news outlet has used the picture below and on the left to describe today’s news, instead of the one on the right that more accurately describes Simmons’ personality.

I’m not going to even try to be unbiased in this article. I am an avid follower and huge fan of Simmons. If his next job was on the drive-thru for McDonalds then I’d gladly join on as a burger flipper just so I could hear him compare customers to obscure past-Celtics who won championships before I was even born.

Either way, no one can debate how influential he is. His climb from Boston bartender to the most popular sports columnist on the planet was meteoric, and he has carved out an empire for himself in the sports world in many fields.

He is a New-York-Times best selling author for his 700 page authoritative account of the last 50 years of NBA history The Book of Basketball. He has created and runs two websites, his baby Grantland.com that draws around 3 million unique visitors per month and focuses on funny, insightful long form blog posts, and Fivethirtyeight.com which focuses on stats and analytics. He hosts his own television show The Grantland Basketball Hour and makes appearances on both NBA Countdown and the NBA Draft. His podcast, The BS Report, was voted the best sports podcast on iTunes and has included guests like President Barack Obama and Larry Bird, to Arnold Schwarzeneggar and Mark Wahlberg. He co-created the wildly successful documentary series 30 for 30, and boasts more than 3.69M twitter followers.

That’s an incredible resume for anyone, so why would ESPN choose not to renew his contract? Simmons is currently making $3 million dollars per year, which is substantial and one can only assume that he was asking for even more in his extension.

However, there have been questions on whether he is truly worth that much. Due to Simmons’ unwillingness to commercialize the site, and create “churn and burn” content that draws traffic but lacks substance, the site has been unable to go mainstream and draw in the mass audiences that I’m sure ESPN executives were hoping for, in addition to limiting revenue and for the most part operating in the red since it’s creation in 2011. He also completely shields his writers from traffic data that their work is gathering, hoping to maintain the integrity of their work, but at the expense of the complaint that they have less incentive to draw in new readers.

Beyond money, Skipper was surely wary of the power and influence that Simmons draws in every project he is involved in, called by a source the “shadow president” of ESPN. According to (the always-reliable *cough*) Deadspin, he influenced a decision to replace Michael Wilbon on Inside the NBA with his friend Doug Collins, leading to Magic Johnson leaving his role as an analyst (he swears this isn’t the reason and both sides have told the public that they are good friends).

There was also the notable spat with Mike and Mike‘s Mike Golic, whose comments about something Simmons had said sparked a strong-worded twitter rant from Simmons and tension between two of the highest profile members of the company.He is truly a “my way or the highway” type guy, and despite the fact that most of his ideas are correct, his inability to be governed makes him a difficult employee to control.

He has been suspended many times by ESPN for comments that are candid and not politically correct which have criticized ESPN and its partners. Any attempt at censoring Simmons sets him off, and there was rumblings of him from several months ago not wanting to renew his contract when it expires in September. Whether you see him as a pest or a great symbol for free speech in a heavily commercialized “don’t say anything bad about our sponsors” world, Simmons is truly the most polarizing character in the company.

But the news wasn’t entirely out of the blue for those who follow Simmons closely as I do.

He’s voiced his criticism of ESPN many times. In fact, a piece he wrote when he was still with AOL in which he shredded ESPN and the ESPY’s was the thing that got their attention and got him hired in the first place. Through the years he’s dropped breadcrumbs of discontent and called for change in the company.

In a very telling interview with recode.net he said “I think they take it for granted. Not just how hard I work, but how hard everybody works,” in which he explained he was upset at ESPN not investing more effort in taking Grantland to the next level. He told Rolling Stone “If ESPN doesn’t have the broadcast rights to the NBA, it will make me re-evaulate what I should do next. I want to work for whoever has the NBA.”

The other thing he certainly is is a rare commodity. No doubt suitors are already lining up to be his next landing spot. He brings with him a huge and faithful audience and a mystique surrounding any controversial figure. Attaching his name to anything draws headlines and plenty of traffic. Whether you love him or hate him, you cling to every corny joke and ridiculous but spot on comparison so you can agree or flame him on twitter (he doesn’t read his twitter replies so save your breath).

The real question is what’s next for the multimedia superstar, and what is the fate of his biggest creation, Grantland.

Let’s start with Grantland.“It long ago went from being a Bill Simmons site to one that can stand on its own,” Skipper said of Grantland. False, Bill Simmons is Grantland. Every major decision from it’s formation to it’s upkeep the last 4 years has run directly through him, and it was he who poached many talented writers from other outlets such as Sports Illustrated to The New York Times. Not to mention that he is undoubtedly the site’s biggest star and biggest draw. And his employees love him. Simmons’ genius extends past the strokes of his keyboard, as he has hired other smart and entertaining men around him who have made Grantland into a beloved site with a cult-following.

Danny Chau, one of the chief editors and publisher for the site, has already given ESPN his notice that he is leaving the company. Could there be more to follow? The Grantland community is certainly very tight-knit, but will these people follow him and put their paychecks in danger? Let’s not take off the table the possibility that Grantland tries to maintain without Simmons, but takes on water for a few months before ESPN shuts it down within a year. What then?

That all depends on what Simmons is going to do.

He could, based on that quote about the NBA television rights, certainly join with traditional powers Fox and CBS who are looking to rival ESPN for sports television dominance and could certainly use the shot in the arm. It’s a safe bet, and he could acquire a role similar to what he has now. However, I doubt either of those outlets would give Simmons the leash that he desires, and I really doubt he wanted out of ESPN just to be put back in the same exact position with new suits overseeing him.

HBO is flourishing right now and could look to expand their sports department, which is currently headlined by “Real Sports with Bryan Gumbel,” a once-a-month serious reporting newsmagazine show that keeps it very real and has itself been in trouble for candid, non-PC statements.

Another possibility is late-night, for sports. Simmons worked with Jimmy Kimmel as a joke-writer for several years and the two remain close friends. Simmons has also confessed on his podcast to be a huge fan of David Letterman.

In an interview with John Ourand, Simmons admits that “you always hear about people talking about ESPN having a ‘Daily Show’ or a Bill Maher-type show, but it would be really tough for them to have a show like that because there’s no schedule continuity.” He goes on to say “they talked to me about having a late-night show in 2010. It would have been impossible because you’re getting pre-empted 60 percent of the time.”

However, through HBO or some other cable outlet, perhaps we could see the emergence of a sports late-night show, combining Simmons’ love for sports and pop culture as well as his fascination with the real lives of celebrities. On those channels or on-demand online he wouldn’t have to worry about live programming such as games or other events knocking his show off.

According to Business Insider, “All I’ve heard is that he wants to go it alone,” says one digital media executive.”I heard he might just want to go independent but get investment, promotion, sales, tech platform from a partner,” says another.

At first I thought this was ludicrous, but the more I think about it, it makes a lot of sense. If there’s a personality who could pull this off, it’s Simmons, I mean think about the success Glenn Beck had doing the same thing in the political realm.

An internet giant such as Yahoo or AOL (the site that gave Simmons his start) could invest the money in an independent site run entirely by Simmons. He could poach of many of the writers from Grantland, and continue to produce all of web-only content he is already doing (podcasts, web shows, written posts ect). Also keep an eye on VICE, who maintains a rogue persona that could be attractive to Simmons, and authored some tweets yesterday showing his strong desire to hire Simmons, though they have since been deleted check them out here.

If the startup cash is big enough, business insider is projecting he needs at least $10 million, I think he could convince his old staff to walk out on Grantland and resume their normal working duties for him at his new gig, if for no reason other than I think Simmons really wants to “stick it to the man,” a trait that I don’t want to peg on his small stature and humble beginnings. He sees himself as an outsider, an outlier, and has somewhat a “me and my people versus the world” mentality. Here he could truly be his own boss, something that he clearly wants and somewhat needs.

The knock against this plan is that his current business model (quality over commercialism) isn’t build to draw in a profit on its own, and that Simmons needed the umbrella of ESPN’s massive budget to support him. But his business could expand. I don’t see why he couldn’t sell programming to say Netflix (which already has a deal with his 30 for 30 series) for things like The Grantland Basketball Hour. If anything, he’s been a progressive, and in a country where more and more people are cutting the cable cord and going to an internet-only media diet, now could be the perfect time.

No matter what happens, I can guarantee you that Bill Simmons won’t go quietly into the night.