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Olbermann’s biggest threat to second ESPN success is Olbermann himself

This is a statement I may regret making in a few months.

But I have a hunch that famously difficult broadcast genius Keith Olbermann is going to be more successful than most critics imagine when he returns to ESPN2 for his new show Olbermann on Aug. 26, broadcasting at 11 p.m. from ABC’s Times Square studios.

There is, on the surface, little evidence for this notion. Olbermann’s penchant for strife with bosses and complicated office antics — which many of us who cover TV thought reached a zenith with his unceremonious exit from MSNBC in 2011 — only seemed to expand with his contentious departure from Al Gore’s Current TV channel about a year later.

It’s also well-established that the 54-year-old broadcaster has worked for — and sometimes butted heads with — just about every major name in television, including Fox Sports, ABC Radio Network, NBC, MSNBC, CNN and, of course, ESPN.

Still, there’s no doubt it will be delicious theater to see if the guy who spoke the first words on ESPN2 — appearing on a youth-oriented version of SportsCenter that he hated, Olbermann said “Welcome to the end of my career” — can eat enough crow in his return to succeed.

But that’s not why I think Olbermann will do well in his new home. He’s also got an undeniable talent for connecting with the camera; an instinct for for how to deliver his patented blend of cynical, smarty-pants analysis, wry humor and passion for fairness as he sees it.

Those skills helped him serve as one-half of SportsCenter’s most legendary anchor team in the 1990s. Later, it helped him build his Countdown show into a liberal-oriented showcase that MSNBC expanded into a channel-wide programming strategy, developing the anchor careers of Rachel Maddow and Lawrence O’Donnell in the process.

There are a precious few people who get fired from or quit major broadcast jobs in the way Olbermann has and still land another chance. That’s because he has an ability that probably even he can’t fully explain; when it works, it pulls viewers in like few other people can manage.

And yet, that’s not why I think he’ll ultimately succeed, at least for a while, at ESPN2. Olbermann strikes me as the kind of talent who often performs best when he’s not at the top of the mountain.

For some people, striving for success is what keeps their worst habits in check. Limited in what they can demand or expect, their talents are focused on succeeding well enough to remove the restrictions they may imagine are holding them back — the need to kowtow to a superior, bend to feedback from others, play office politics games effectively, or something else.

I base this idea on my observations of other talented media professionals with a penchant for self-sabotage –not naming names here — and my interview in 2003 with Olbermann himself.

He was fresh off his departure from Fox and pulling together this new show for MSNBC called Countdown. Back then, it was a cheeky list of the day’s most absurd news stories, delivered like an odd hybrid of an actual newscast, an episode of The Soup and a bit from The Daily Show.

As I noted in a blog post about Olbermann’s MSNBC departure: “In those days, Olbermann had a lighter touch and seemed aware of how much his past battles had cost him. Even now, he seems a uniquely tortured personality, capable of brilliant broadcasting and awfully petty action, sometime in the same breath. But his early success with a lighter, anti-Fox Countdown gave MSNBC the breathing room it needed to make a turn towards an alternative.”

In our 2003 conversation, he batted back rumors that his temper had cost him jobs, while admitting that he was hoping to handle himself better in the future. It may sound like the song we heard when he left MSNBC for Current TV, but at Current he was given more autonomy, essentially placed on top of a small mountain created by the channel itself.

I’m hopeful in this new gig, Olbermann will get back to that place where he seemed to be a decade ago; aware of his own missteps and eager to build a new kind of television.

If he works that out on ESPN2’s Olbermann, we only have to worry about what happens after he pulls it off.

Read more about this and other media issues on my blog for the Tampa Bay Times, The Feed, by clicking here. Info on my new book, Race-Baiter, can be found here.

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