Love him, hate him, or think he was good to start but went way past his stay-fresh date (my take), if you're a modern sports media fan, you can't ignore Bill Simmons, who has largely become the face of ESPN in the last 15 years, but will no longer be so after September, with his contract not being renewed.
So, who replaces him in general, and more specifically, running the Grantland portion of ESPN, which I assume John Skipper continues?
I and a friend brainstormed this.
There's only one realistic internal choice that we see: Keith Olbermann. Nobody else, whether at Grantland or the whole of ESPN, has a combination of professional chops and a "rainmaker" style to bit the bill.
That said, in previous tenures at ESPN, Olbermann's envelope-pushing on some of his rainmaking has produced as much corporate angst as Simmons', so this may not happen. And, at 55, he may not profile young enough to replace Simmons.
Nate Silver? While Simmons was right about Grantland, he was wrong about 538, which has been a flop at ESPN, to the point that, as in telling us that Willie Mays actually, truly, was better than Alex Rodriguez (as if Baseball-Reference can't?), it's increasingly operating in Captain Obvious territory. Plus, Silver doesn't strike me as "rainmaker" type. (And, per the likes of that, that doesn't even touch whether or not ESPN cuts back on backing for 538, or even kills it, after Simmons is gone.)
So, from the outside?
Said friend mentioned Will Leitch of Sports on Earth. He's got the professional chops and is respected. He's younger than Simmons, which could help on the rainmaking side, as could his angle in starting Deadspin, which gives him a bit of snark. He doesn't seem to have baggage, other than, like Simmons, being a big homer — Leitch for the St. Louis Cardinals, Simmons for the Boston Celtics, even if he doesn't dive too deep into homerism for individual players, like Larry Bird and Bill Russell.
On the other hand, if Leitch is intellectually lazy enough to put David Blatt ahead of Larry Brown and Red Holzman in the NBA Jewish pantheon, he's writing himself out of the running.
I mentioned Jeff Passan at Yahoo, but he was ixnay on that. Dan Wetzel might be another option.
That said, where's Simmons land?
Said friend mentioned Sports Illustrated, which recently announced it would get into documentary video work. (As in, 30-for-30 stuff.)
OTOH, does SI have the platform reach to under-50 folks anymore? (Of course, Simmons is 45 and not getting younger; that said, he's not necessarily getting more mature, either.) And, as a bit of the battered remnants of the print-first Time empire, does it have the money to pay Simmons' ask, let alone front all that he might want to do?
What about Yahoo, speaking of? It's got money from its sale of Alibaba, and a need to increase its visibility. This would certainly do that.
Finally, when does Simmons land? His contract expires in September. Does ESPN have a non-compete? If so, is it enforceable, even if he lives in California, which bans non-compete clauses in contracts? If there is one, and it's non-enforceable, could ESPN still get an injunction to keep him off the Internet outside the Golden State? Stay tuned.