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

Olbermann's peripatetic employment history is well-documented, from his firing from Fox Sports by Rupert Murdoch, who called him "crazy," in 2001, to his abrupt departure from MSNBC in 2011 after being suspended (then reinstated) for making political contributions to Democratic candidates the year before. "I was going to write a book about my television experience. I have the title, Figments of My Ego. The problem is that right now, it would have to be a 17-volume set," he says. His clashes with colleagues and management have been elevated to epic proportions in multiple books, including James Andrew Miller and Tom Shales' Those Guys Have All the Fun (ESPN executive vp Howard Katz: "He was tearing the newsroom apart"; former ESPN chairman Herb Granath: "I was enraged" by him) and Michael Freeman's ESPN: The Uncensored History (Olbermann made sportscaster Suzy Kolber cry when she was paired with him on ESPN2's SportsNight). Fairly or not, this makes Olbermann what they call in football a "risky prospect."

Skipper characterizes it as a "calculated gamble." He reasons: "It comes down to deciding if the potential upside will outweigh the potential downside. I am not naive going into this. I am optimistic; I believe it's going to work. And if it does work, there is very significant upside for us."

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The potential for greatness is the reason Olbermann keeps getting jobs; for example, he'll also cover the MLB postseason for Turner Sports in a nonexclusive deal. Not only does he have an innate ability to connect with audiences, but he's an original thinker who is absolutely unafraid to say anything, no matter whom he might offend.

"He doesn't suffer self-doubt," observes Jamie Horowitz, the 37-year-old vp original programming and production who is heavily involved in the launch of Olbermann. "He's incredibly sharp. You add up all the IQs in the room, and he's still ahead by 50. When you ask him for his take on almost anything, he's assertive and strong."

Norby Williamson, ESPN executive vp programming and acquisitions, who joined the network in 1985 as a production assistant and was Olbermann and Patrick's producer on SportsCenter, was a driving force in bringing Olbermann back to the sports network. "He's a brilliant writer," says Williamson. When the executive was working as a producer on the 11 p.m. SportsCenter, "the anchors would always be pushing you to get the rundown from 3:30 on so they could start writing before the games start at 7. I would get the guts of the rundown in by 5, and then I'd go out and get something to eat. I'd come back at 6, and he'd be just sitting there: 'Yeah, I'm done.' He would turn around stuff that was very sophisticated, analytical, informative, funny, offbeat in an hour. It would be done at an exceptionally high level, and that happened night after night after night."

John A. Walsh, the éminence grise of ESPN who is a consultant on Olbermann's show, spent five years trying to recruit him to the cable channel the first time. "My first day at ESPN in 1988, the first tape I looked at of prospective candidates was Keith Olbermann. I said to my colleagues, 'Man, this is going to be an easy job,' " recalls Walsh. "Keith was always trying to push us to go further, trying to push us into uncomfortable areas. Although that tension doesn't feel healthy at the time, when you look back upon it, you realize how healthy it was."

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The current show's mission, for Olbermann and his producers, is to rediscover -- and have audiences reconnect with -- the erudite, mischievous and insightful sportscaster. Olbermann will mix commentary, interviews and sports highlights and also will include a revival of the "Worst Persons in the World" segment that was a staple on Countdown. There also will be a "This Day in Keith History" segment that will give Olbermann the opportunity "to make fun of his glasses, mustache and ties," explains Horowitz.

There is nothing in his ESPN contract that precludes him from talking about politics. His producers already have reached out to George W. Bush, a former owner of the Texas Rangers. They have yet to receive a yes -- or a no. (The radio silence might be attributed to the former president's recent heart surgery.) And Olbermann also would like to have President Barack Obama as a guest. But his forays into politics only will be as it relates to sports. For instance, in a rehearsal just days after Milwaukee Brewers star Ryan Braun's seasonlong suspension for taking banned substances, Olbermann delivered a nine-minute opening commentary on the impact Braun's suspension would have on New York Yankees third baseman Alex Rodriguez, currently appealing an Aug. 6 suspension for use of performance-enhancing drugs. "Keith is a singular talent," says Horowitz. "He can deliver unique indictments of unfairness in sports. When he finished that Braun commentary, the whole control room just took a breath and looked around, and it's like, 'Oh, that's our show.' "

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