Bill Simmons leaving ESPN is without doubt *the* sports media story of 2015.  Had The Sports Guy chosen to stay at ESPN, it would have presented a couple of compelling questions… but nothing like his leaving does.  With ESPN saying sayonara to Bill Simmons, not only will we see one of the great free agent races in the history of sports media, we will see ESPN go through major transitions through many of its top enterprises.  The dominoes that are about to fall could alter the sports media landscape for years to come. Here are the 9 biggest questions now that we know Bill Simmons is leaving ESPN.

1) Will Bill Simmons work through the end of his contract in September?

Right now this is the biggest unknown.  As of midday yesterday, it seemed to be totally up in the air as to when Simmons would work his final day with ESPN according to the sources we talked to.  It was a bold play for John Skipper to make the pre-emptive announcement in saying that ESPN would not renew Bill Simmons’ contract in September.  You may have noticed that September is a full five months away. So what do ESPN and Bill Simmons do until then?  Do they awkwardly pretend that everything is normal and go on with business as usual?  Does ESPN tell Simmons to sit on the sidelines until September?  Or do the sides come to a mutual agreement to let Simmons out of his contract early so he can pursue whatever is next?

We’ll find out soon enough.  The Grantland Basketball Hour’s next new episode is scheduled for Tuesday, May 12th on ESPN.  To be honest, I’m a little disappointed ESPN hasn’t sold this as a Decision-level special edition.  All we need is Jim Gray there to interview Bill if he shows up!

2) If Simmons is still working through September, does he go scorched earth?

Simmons has long been known for his outspokenness, especially when it comes to criticizing colleagues at ESPN.  You may remember his Twitter rant aimed at Mike and Mike that somehow escaped discipline from ESPN higher-ups as the most recent example.  Now that Simmons is officially leaving, what’s stopping him from sharing what he really feels about the likes of Mike & Mike and Skip Bayless and more?  That’s why it might be wise for ESPN to have Simmons quietly disappear now before something like this happens…

3) What will Simmons say when he does tell his side of the story?

Credit John Skipper for this – he made the first move.  Skipper making the announcement that he wouldn’t renew Simmons’ contract allowed him to set the narrative.  It gave him the opportunity to get ESPN’s side of the story out there first and say that it was his and his network’s decision.  It allowed Skipper to tell the world that no one person is bigger than the four letters and that ESPN and Grantland and all the other properties will be just fine without Bill Simmons.

And even though Simmons remained silent all day on Friday, you know a response is coming.  This is Bill Simmons we’re talking about!  He has something to say about everything, and usually thousands of words at that.  Where, when, and how Simmons chooses to tell his side of the story will be fascinating.  And given that Simmons was reportedly “blindsided” by the news breaking on Friday, my guess is that his opening salvo will be strong.

4) Does ESPN shift away from personality-centric endeavors?

If it’s metaphysically possible, hell has frozen over multiple times in the last couple years.  Two of ESPN’s prodigal sons, Keith Olbermann and Jason Whitlock, have been welcomed back home with open arms.  Olbermann infamously napalmed his bridge back to Bristol while Whitlock emerged as one of the network’s biggest critics after leaving Bristol.  Now the two are leading personality-driven programming on television and online under the ESPN umbrella.

And although John Skipper has been high on handing out olive branches and letting bygones be bygones, with big personalities come big risks.  For instance, Skipper betting the success or failure of The Undefeated on Jason Whitlock seems to be coming up snake eyes at the moment.

There was no bigger personality at ESPN than Simmons.  Now that the network has walked away from the negotiating table, what happens to people like Whitlock and Nate Silver and others that ESPN has invested so many resources in?  Does Skipper’s willingness to let Simmons go mean ESPN will return to the days where they de-emphasize individual personalities so no one person accumulates that much power and influence?  Will ESPN attempt to ensure nobody of Simmons’ stature is able to become instant competition some day?

ESPN helped to create Bill Simmons, now they’re going to have to deal with him.

5) So… who is the new Alpha at ESPN?

Bill Simmons was numero uno at ESPN.  Nobody drew the traffic or the buzz or the intrigue that he did.  Now that Simmons is gone, who becomes ESPN’s franchise player?  It’s a really difficult question to answer because nobody carried the clout that Simmons did with fans and in the boardrooms in Bristol and Los Angeles.

Is it an ESPN lifer like Bob Ley or Chris Berman?

Is it a trusted face on television and radio like Scott Van Pelt?

Is it an outspoken personality like Michelle Beadle?

Is it, gasp, Skip Bayless or Stephen A. Smith?  (Smith’s absurd salary gives him as good of a case as anyone.)

Is it Gonzalo Le Batard?

There isn’t anyone that we can point to at the moment who takes the mantle of being the face of the network, which proves just how difficult it will be to replace Simmons’ popularity and reach.

6) What happens to Grantland?

Bill Simmons’ signature achievement at ESPN was the launching of Grantland in 2011.  It was one thing for Simmons to gain millions of readers for his columns and listeners for his podcasts.  This was much more ambitious, though – an entire site dedicated to Simmons’ je ne sais quoi.  The vision of Grantland was quintessential Simmons – a mix of sports and pop culture that had no real boundaries of which to speak of.  And although the original site was tied closely to its founder, Grantland has grown to the point where it houses an impressive roster of sportswriters and pop culture scribes.

But how does Grantland get along without Simmons?  Many of the writers brought in are Simmons disciples and loyalists.  Do they leave with Bill and follow him to his next venture?  Grantland’s profitability and long-term viability has always been riddled with doubt even with Simmons on board.  Now with the biggest click magnet leaving, can Grantland survive, let alone thrive?  Without Bill Simmons, does Grantland become another Sports on Earth?

A piece of information that flew under the radar is Grantland publisher David Cho also leaving ESPN, so the shakeup at the vertical will go much deeper than Simmons’ departure.

7) And what about 30 for 30?

If Grantland is Simmons’ signature vehicle, 30 for 30 may be his greatest achievement at ESPN from a content standpoint.  30 for 30 has been the defining factor in leading ESPN to the top of the sports documentary field.  It’s produced some of the most compelling programming in the 35+ year history of the network.  New episodes continue to roll out each year that are of the highest quality.  Even the most optimistic person inside Bristol could not have forseaw the popular success and critical acclaim that would come with 30 for 30.

As uncertain as Grantland’s future may seem, there does seem to be a solid enough infrastructure within ESPN Films and 30 for 30 that the show will go on – namely, the existence of Exit 31 (the unit which houses Grantland, ESPN Films, and 538) and the leadership of Marie Donoghue and Connor Schell.  With much of the drive for 30 for 30 coming from the individual filmmakers and ESPN Films, 30 for 30 should be a central pillar of ESPN’s original programming for quite some time.

8) What does Bill Simmons truly value in his next move?

The free agent frenzy for Bill Simmons will be great media theater that will crossover into the mainstream, let alone make waves in the sports world.  The question for Simmons will be what does he truly value in his next working environment, because many of his likely landing spots can offer different strengths.

Rupert Murdoch can write a blank check to build Fox Sports 1 around Simmons.  An entire network could be in the palm of his hands.

Turner Sports can offer him the online realm of Bleacher Report (whose readership is growing closer to ESPN by the day) and a television gig with his beloved NBA as the next Charles Barkley.

Online outlets like Yahoo present a huge platform for columns, podcasts, etc..

Even a cable company like HBO could give Simmons something he never had before: an unfiltered television presence.  (Hey, it worked for Joe Buck, right?  Errr… kinda?)

And then there’s the independent option, which could finally give Simmons the complete editorial freedom that he never received at ESPN.  What his true priorities are might lead him to his next stop.

9) Can Bill Simmons and ESPN really be better off without one another?

This may be the ultimate question that needs answering.  The marriage between ESPN and Bill Simmons created an empire never before seen in sports media.  Love him or hate him, Bill Simmons showed that it was possible for a fan and a blogger to become one of the most widely-read and powerful individuals in sports.  If Bill Simmons can go from Boston Sports Guy to millions of followers at ESPN, it gives hope to all of us that we could get that break some day.

Here’s a couple of truths that can’t be denied: Bill Simmons will never have wider reach than what he had at ESPN.  No matter where he goes, he’ll never have the same readership for his columns, or the same number of listeners for his podcasts, or the same number of viewers for his television shows.  They don’t call themselves the worldwide leader for nothing.

Likewise, the loss of Bill Simmons will hit ESPN harder than any other talent that has left the network.  The reverberations throughout Grantland, 30 for 30, podcasts, and television will be massive.  Simmons is ESPN’s largest digital presence by far and brings millions of listeners and readers to ESPN platforms.  How does ESPN even begin to think about replacing someone who has been such an intricate part of the network’s success as a front-facing personality and in an executive role?

One can’t help but wonder whether Bill Simmons and ESPN will ever be able to accomplish apart what they did together.

About Matt Yoder

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