It’s been seven days since John Skipper channeled his inner Donald Trump (or Vince McMahon as the case may be) and told the world that he no longer required the services of Bill Simmons.  While we still don’t know what the immediate future holds for the two sides as what remains of Simmons’ ESPN career hangs in limbo (UPDATE: Simmons is done at ESPN), we can look back at how we got to this point.

The ESPN-Simmons divorce did not happen im the spur of one moment.  Rather, there were several moments that chipped away at the foundation of the relationship and ultimately caused it to crack.  Here is our list of the 8 moments that led to John Skipper’s announcement a week ago that Bill Simmons would not return to ESPN after his contract expired in September…

1) Simmons pops the Bristol Bubble – May 2011 

There were a few moments of controversy between Bill Simmons and ESPN before he signed a new contract in 2010. The two major ones were the ruckus over ESPN nixing a planned BS Report between Simmons and then presidential candidate Barack Obama in 2008 and his first Twitter suspension in 2009 for criticizing personalities at WEEI.

Nevertheless, all was well in 2010 when Simmons re-signed with the company.  He was gaining television time, he was creating Grantland, life was good.  Life was peaceful.  Then came the first rumbles of thunder over the horizon in Jim Miller’s oral history “Those Guys Have All The Fun.”  In the book, some of the most bombastic and juicy quotes came from Simmons, who called out various colleagues including Mike Tirico for his comments on how the Monday Night Football booth with Tony Kornheiser imploded:

Tirico doesn’t sell for Tony for three f*cking years, then has the gall to say nice things about him after Tony leaves?  Come on.  What kills me is that Tony got the rap for blowing this when nobody on the planet can succeed in TV if their play-by-play guy isn’t selling them.  Five minutes into their first regular-season Monday night game, Tirico had already laughed at more Gruden jokes than he did for three years of Kornheiser.

That would only be the start of Bill Simmons speaking his mind regarding his co-workers.

Simmons also opined about the Bristol bubble and enjoying life outside the ESPN campus. Over the years that would follow, it was Simmons’ deteriorating relationships with those ESPN executives in Bristol that would ultimately lead to the divorce:

“I need to figure out a way that I can operate in my own sphere and not deal with Bristol as much.  Nothing against Bristol, but I do worry that it becomes a little cultish after a while.  You go there and there’s ESPN everywhere.  At the cafeteria, there’s Mike & Mike getting a sandwich… It’s really hard to think out of the box when you’re trapped in that box the whole time… that’s one of the reasons PTI succeeds – it’s in Washington, it’s out of the box, they leave it alone.”

2) Simmons gets suspended for criticizing First Take – March 2013

Bill Simmons was suspended for a week after daring to criticize the golden calf of ESPN – First Take and Skip Bayless.  Simmons’ comments were motivated by pre-nationwide fame Richard Sherman tearing into Bayless on the program.  In the end, the embarrassing segment and the subsequent suspension revealed ESPN’s inner-identity crisis that still exists to this day.  And it was the first sign that ESPN actually valued Bayless more than Simmons.

3) NBA Countdown falls apart before our eyes – June 2014

In spite of the bumps in the Simmons-ESPN marriage, the two sides still seemed to still be thriving together by the summer of 2014.  Simmons had even been given a lead role on NBA Countdown as one of the network’s top studio analysts.  As part of his expanding television presence, ESPN built the new and improved Countdown around The Sports Guy as their answer to Charles Barkley and Inside the NBA.  (Simmons denied a report from Deadspin’s John Koblin that he helped push out Magic Johnson and Michael Wilbon after the previous season.)

It blew up spectacularly.

During the 2014 NBA Finals, Simmons openly sulked about his lack of airtime on live television by snapping “do I get to speak now?”  That quip drew a very visible headshake from Sage Steele.  Simmons would not return for the next season and was given his own personal playground in the Grantland Basketball Hour.

4) The 3 week suspension – September 2014

I really hope somebody calls me or emails me and says I’m in trouble for anything I say about Roger Goodell. Because if one person says that to me, I’m going public. You leave me alone. The commissioner’s a liar and I get to talk about that on my podcast … Please, call me and say I’m in trouble. I dare you.

Bill Simmons asked for it, and his bosses answered.  After calling Roger Goodell a liar on his podcast and then daring his bosses to punish him for it, they did just that.  Simmons was given a three week suspension, one of the harshest in ESPN history.  If there’s anything on this list that was the biggest contributor to the fracturing of Simmons’ relationship with ESPN and President John Skipper, it was this decision.  Both sides seemingly sent the message that ESPN wasn’t big enough for the two of them.

5) Simmons goes scorched earth on Mike & Mike – November 2014

Simmons’ tweets about Mike & Mike made his First Take critiques look like they were fired with a pea shooter.  He went on a full-out Twitter rant aimed at the ESPN Radio morning show after he believed they took some of his comments out of context and accused him of trying to grab headlines.  Amazingly, Simmons was not suspended for calling the longtime ESPN flagship program “absolute garbage.”

6) ESPN plays Scrooge – December 2014

ESPN oracle Jim Miller has said it was “over” after this happened.  When Simmons was suspended for three weeks in the fall, two of them were reportedly unpaid.  Waiting until the Christmas season to do so and pull the money from his paycheck was a twisting of the knife that it was always going to be hard to come back from.

7) Lack of support for Grantland – March 2015

While not a “moment” by definition, this interview with Re/code revealed an internal struggle between Simmons and ESPN executives over his brainchild Grantland.  Simmons expressed frustration over a lack of staffing for the website and how the network took both his work, and the website, for granted.

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.

Another Grantland story that cannot be forgotten is the tragic death of Essay Anne Vanderbilt that rocked not just the vertical, but ESPN and sports media as a whole.  Her suicide was trivialized as a mere footnote in a larger expose on the website.  It was a story that was first lapped up by #longform #journalism aficianodos, then universally condemned for its lack of sensitivity when the LGBT community raised serious concerns.  Simmons faced up to the fallout from the article in a contrite open letter, but one wonders how much it may have damaged Simmons’ editorial clout (and the influence of Grantland) behind the scenes that such an ill-fated article was published under its banner.

8) Simmons disses Roger Goodell (again) on The Dan Patrick Show – May 2015

Who would have thought an old Mick Foley catchphrase would be the final nail in the coffin of Simmons’ ESPN tenure?  Simmons has appeared on The Dan Patrick Show plenty of times, he’s criticized Roger Goodell plenty of times… but when he pinged the commish for a lack of “testicular fortitude” it was apparently the final straw for ESPN President John Skipper.  In an uncharacteristically impulsive reaction, Skipper went public to the New York Times the next day to say he wasn’t renewing Simmons’ contract in September.

After all of the above moments, it’s somewhat ironic that all it took was a rather inconsequential radio interview for Skipper to hit the big, red, shiny button on Simmons’ 15 year ESPN tenure.  Alas, given all the sniping and suspensions and strife since Simmons re-signed in 2010, perhaps the parting of the ways was inevitable.

About Matt Yoder

Award winning sportswriter at The Comeback and Awful Announcing. The biggest cat in the whole wide world.

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