Keith Olbermann Defaces A-Rod; Reveals Apologies, Drama Behind ESPN Return

This story first appeared in the Aug. 23 issue of The Hollywood Reporter magazine.

Keith Olbermann is not much of a martini drinker. But the former SportsCenter anchor was following the lead of his host. So when ESPN president John Skipper, a North Carolina native with a disarming Southern drawl and an expertise in 18th century British satire, ordered a Beefeater martini on the rocks with a twist, so did Olbermann.

"I have never ordered a martini any other way since," he says.

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It was March 19, 2012, an unseasonably warm, late-winter evening. They were in the capacious dining room of the Four Seasons Restaurant on Manhattan's East 52nd Street. "I had never met Keith despite his prominence in the history of ESPN," recalls Skipper, who had been plucked from Disney's publishing group to start ESPN The Magazine a decade and a half earlier in 1997, the same year as Olbermann's exit, one marked by controversy over management clashes. "I am post the Keith troubles," notes Skipper.

The two men bonded over a three-hour dinner, during which assorted war stories were shared by Olbermann, whose ESPN tenure from 1992 helped define the personality-driven sports channel with his premier highlights program SportsCenter (along with co-host Dan Patrick). At some point during the dinner, Olbermann whispered to Skipper that his present job as the anchor of his Countdown With Keith Olbermann show on Current TV -- the network launched by former Vice President Al Gore with his friend and Democratic operative Joel Hyatt -- "was probably not going to make it to the end of the week." Recalls Skipper: "But we left with nothing more than a, 'Hey, it was good to get to know you a little bit.' I think he was wise to begin to try to set a personal relationship."

Eighteen days after Olbermann and Skipper met for dinner, and less than a year into a $50 million contract, Gore and Hyatt very publicly fired Olbermann.

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Over the next year, the 54-year-old anchor would battle Current in a bitter lawsuit that finally would end in March with a multimillion-dollar settlement in his favor. He also would attend a series of clandestine meetings at musty Connecticut restaurants with various ESPN executives; acquire a dog, a girlfriend and a raw food diet while intensifying his yoga practice (he has lost 20 pounds); and decide that what he really wanted to do was return to sports, specifically sports at ESPN.

Skipper and Olbermann would not talk again until July 16, 2013, the day before ESPN announced that Olbermann would return to the company as the host of a late-night sports and commentary show on ESPN2. Network executives had been trying to mount a late-night franchise on the sister channel for a few years, including going after Seth Meyers, multiple knowledgeable sources tell The Hollywood Reporter (more on that later). But to Olbermann's delight, they ended up with him.

"I could see it on my tombstone, or at least in my obit: 'Keith Olbermann, who left ESPN in a tempest …,' " he says, somewhat wistfully. It is Aug. 8, and Olbermann and I are having lunch at the Atlantic Grill on the Upper East Side, just around the corner from his apartment. There is much more white in his hair since he left Current, and he is wearing baggy, faded jeans and a brand-new black polo with a small, red ESPN logo on the breast. "What I would like to go for is: 'Keith Olbermann, who left ESPN in a tempest in 1997 and then returned later and retired with a gold watch.' I'd like to give that a shot, having repaired most of the damage. I think that really would be great."

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On the face of it, Olbermann's return -- his eponymous show Olbermann bows at 11 p.m. Aug. 26 -- marks one of the most improbable reunions in television history. Brokered by his agent, Nick Khan of CAA, and his manager, Michael Price, the two-year multimillion-dollar deal will restore him to a network that despite Olbermann's 16-year hiatus still employs some of his fiercest detractors. It also will give one of the more prominent serial feuders in the industry -- during a detour from sports into polemical commentary on MSNBC, he made enemies on the right such as Fox News rival Bill O'Reilly and Sarah Palin (whom he called "very stupid") -- a perch with a bullhorn. Yet despite Olbermann's pugilistic reputation, his raw talent never has been in doubt. For ESPN -- which, though it had 16 of the top 20 cable programs in 2012, is contending with a well-financed insurgency from Fox Sports -- Olbermann represents heavy-duty firepower. And Olbermann is not about to let his personality get in the way of his prize: The never-married sportscaster has begun exhibiting a degree of self-awareness that might surprise some, including the ESPN employees who were on the receiving end of his infamous memos: "I would write a three-page memo outlining why what they wanted to do was wrong and why my experience was right. Even if you're right all the time, those memos get tiresome," he admits.

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