ESPN's John Skipper Wants Keith Olbermann, & Could His Hiring Line Up with Rick Reilly's Departure?

By Jason McIntyre

Sunday night, the New York Times had a curiously-timed story: Keith Olbermann, the most disliked ESPN employee in the history of the network, had dinner with ESPN’s No. 1 suit, John Skipper, months ago. Why was this news only leaking out now?

At first, the story looked like an obvious plant by the unemployed Olbermann – two days before Fox Sports was making a splashy announcement about a new TV channel it hopes will rival ESPN, here’s a story about how the once-toxic Olbermann was now making nice again with ESPN! Fox is in the midst of a hiring spree, and they’re giving a TV show to an 81-year-old … why not give one to the supremely-talented Olbermann?

But after poking around at ESPN, sources tell me this wasn’t a give-me-a-job plea from Olbermann. ESPN President John Skipper wants the cantankerous Olbermann back, multiple sources say, and they’re very likely going to get him – as early as late-May.

The Times story wasn’t a test balloon from Skipper to his employees to see if a revolt would happen – although many privately expressed their dismay to me – it was a test balloon with Disney executives. Ultimately, they will determine whether or not Olbermann goes back to ESPN.

Sportscenter ratings have sagged. Competition in the sports space is suddenly fierce, with NBC and Fox (with MLB Network, Golf Channel, NFL Network, etc) constantly making moves on ESPN talent. If ESPN doesn’t hire Olbermann, someone else eventually would (though a source at Fox Sports says that’ll never happen, given his history with Rupert Murdoch).

What, exactly, would Olbermann do for ESPN?

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Besides tossing him the occasional Sportscenter, Olbermann could start a column on Rick Reilly’s deal is expiring early this summer (June 1 is the rumored date), and if he bolts for the Golf Channel, Olbermann could fill his space. How’s that for media free agency – Reilly walks and Olbermann enters? Or, ESPN could just keep Reilly (not at a “ridonkulous salary”) and add Olbermann?

Another source said ESPN Radio in New York (which recently moved from AM to FM) is struggling beyond Mike & Mike, and an afternoon show (say, opposite Francesa?) could be intriguing. Olbermann is a baseball guy. New York is a baseball town. Baseball Tonight could also be in play, I’m told.

Options are many. But here’s the big fear Skipper may not have considered – in 2013, if Olbermann dresses down employees and curses out production assistants, a source at ESPN texted me, “you know that hours later, it’s going to end up on your site or Deadspin.”

If you’re wondering what Bill Simmons would think of Olbermann’s return – surely you haven’t forgotten their 2011 dust-up – the answer is probably nothing, since he’s based in LA and would never have to deal with Olbermann, who would be based in Bristol or New York.

One person who probably isn’t thrilled is Suzy Kolber. In the great ESPN Book by Mike Freeman, ESPN: The Uncensored History, he detailed how Kolber would go in the bathroom and cry after being berated by Olbermann. He later apologized.

In 2013, a story of that magnitude would hit blogs and then go viral on the web with unimaginable speed.

Olbermann’s old high school buddy, Chris Berman, probably knows something about that.