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.

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.’ “

If Olbermann’s intellect and confidence have made him a star, his inability to suffer fools has left a trail of hurt feelings. Significantly, Olbermann’s new show will not be based at the scene of his past scuffles, the network’s sprawling Bristol, Conn., campus. Rather, it will be filmed at ABC’s Times Square Studios in Manhattan. “There was no intention to do the show in Bristol,” says Skipper. “While we wanted to bring Keith back, to bring him back and march him through the halls of Bristol is probably less than a good idea.”

If he won’t be running into old adversaries in the office cafeteria, he nevertheless embarked on an apology tour of sorts. He published a lengthy 2002 mea culpa on Salon to former SportsNight colleague Kolber, whose pieces Olbermann used to attack on air. And he still seems sorry that she apparently found him so difficult to work with. “Of all the things that I regret, one is that it happened. I mean, you don’t want to provoke anybody to tears but especially a female colleague in what was not a female-conducive environment at that point. It was 10-to-1 men on the [Bristol] campus,” he says. And when he saw her at the Super Bowl in ’09, “we went running at each other with a big hug.”

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When Olbermann left ESPN in 1997, Bob Ley — whom Olbermann succeeded on the 11 p.m. SportsCenter — told authors Miller and Shales: “Our long national nightmare is over. … We felt not so much relief when Keith left as unrestrained f—ing joy.”

After trading e-mails and phone calls, Olbermann and Ley, who still is a sportscaster at ESPN, spoke again July 25, the day after Olbermann’s Q-and-A at the Television Critics Association summer press tour in Beverly Hills. The hatchet was buried in a discussion covering his new role. “We were on the phone for 25 minutes,” says Olbermann. “We had a good talk. He said, ‘Anything I can do for you?’ I said, ‘Bob, practically speaking, when you have something you want to push, bring it to me. Don’t bring it to the producers, bring it to me.’ “

Another potentially acrimonious reunion was averted when Olbermann ran into former colleague and current ESPN personality Chris Berman, about whom he had been less than magnanimous in Shales and Miller’s book: “When I was at CNN [where he worked in the early 1980s], we used to look at ESPN as our comic relief, because for a long time, in terms of sports news, CNN was a 10-times-better product than ESPN. I used to look at my old friend [Chris] Berman sweating away in the studio without a teleprompter, trying to read his notes. I thought, ‘Thank God that there’s somebody on the air in worse shape than we are.’ “

Olbermann’s path crossed Berman’s on July 16 behind the batting cage at Citi Field during the MLB All-Star Game; it was one day before the ESPN announcement was released. According to Olbermann, he planned to reach out to Berman, “not because there was any kind of dispute” but because in the history of ESPN, Berman is a “seminal” figure. “He just looks over and nods at me, and I went, ‘I got something to talk to you about,’ ” he recalls.

By then, news of Olbermann’s impending return already had leaked. “What ensued was one of the best conversations we have had as adults,” he says. “The gist of it was, ‘Why would I have any objection to you coming back?’ And I said, ‘I’m just kissing the ring here.’ And he’s like, ‘Yeah right.’ “

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He also initiated some fence-mending in a series of conversations with Mike Soltys, ESPN’s longtime head of corporate communications. Soltys, who infamously told USA Today that Olbermann did not simply “burn bridges” at ESPN, he “napalmed” them, on July 17 tweeted a link to the official ESPN announcement with a photograph of a construction site with a sign reading: “Bridge Under Repair.”

Of course, some bridges cannot be rebuilt. Which brings this story back to Current. Although Olbermann’s position at Current became rocky less than two months after Countdown bowed in June 2011, he was blindsided when Gore and Hyatt pulled the trigger and fired him March 29 for what they characterized as “serial, material breach of his contract.”

“When you’re working for somebody whom you admired politically, who turns out to be a clod,” says Olbermann, referring to Gore, “the scales fall from your eyes. Sorry. Al underdelivered. I mean that’s just simply the case. I don’t want to dwell on it, but it’s true.” Olbermann countersued, asking for $50 million in damages, and the case slowly proceeded to a confidential settlement in March; three months earlier, Qatari-based news organization Al Jazeera bought Current for $500 million, in all likelihood hastening the settlement. (Asked whether he is happy the Current chapter of his career is over, Olbermann quips, “Let’s just say I bought gifts for my lawyers.”)

Olbermann saw Gore at the arbitration meeting in San Francisco on March 12. Asked whether that was awkward, he smiles ruefully: “Two days before, I’m standing at Phoenix Municipal Stadium with my friend Bob Melvin, the manager of the Oakland A’s, talking about pitching depth. Two days after that, I’m in a mediator’s office, hearing myself described as, you know, akin to Stalin. We are in the middle of a legal proceeding involving large sums of money and contracts. Of course it was awkward.”

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But the experience with Current, he says, crystallized his desire to remake his image as something other than “this intense, belligerent, political polemicist,” he says. “I left ESPN as a sportscaster mostly known for humor and insight.”

As things were unraveling at Current, Olbermann’s representatives set up numerous meetings for him. There was a Dec. 8, 2011, breakfast at The London in New York with Showtime entertainment president David Nevins. Coincidentally, John Cleese, a personal friend of Olbermann’s, happened to be at the breakfast buffet and joined them. “He sat with us for an hour, and the only conclusion we reached was that if I was going to do a show, then John was going to have to be a correspondent,” laughs Olbermann. On March 8, 2012, three weeks before he was fired from Current, he had dinner in a suite at the Carlyle Hotel with ABC News president Ben Sherwood and Sherwood’s deputy Barbara Fedida. About a month later, he appeared with George Stephanopoulos on ABC’s This Week‘s roundtable.

After multiple meetings with ESPN in 2012 — Williamson wanted to have Olbermann back at the network and on ESPN2 by September of that year, just in time for the football season — things cooled as the network pursued Saturday Night Live‘s Meyers, who hosted the ESPY Awards in 2010 and 2011. They heated up again after Olbermann’s March settlement with Current — and after Meyers had reached a new agreement to stay at NBC and succeed Jimmy Fallon on Late Night.

Olbermann’s return to ESPN comes as the network is girding for a potential incursion from Fox Sports, which will launch its own 24/7 cable sports channel, Fox Sports 1, Aug. 17 in 90 million homes against more than 100 million for ESPN and ESPN2 . But FS1 will not have the NFL, the top ratings draw in sports. (Last season, Monday Night Football on ESPN averaged more than 12.8 million viewers, and NBC’s Sunday Night Football stands as the No. 1 program on all of TV with 21.5 million viewers.) When it launches, FS1 will be in the midst of NASCAR; there also will be UFC fights. And co-presidents Randy Freer and Eric Shanks have spent the past year gobbling up rights including Major League Baseball, Pac-12 college football, NASCAR, FIFA World Cup Soccer and U.S. Open Golf. The network also has hired a cadre of anchors, correspondents and contributors including Erin Andrews, Charissa Thompson, Donovan McNabb, Gary Payton, Andy Roddick and 82-year-old Regis Philbin, who will host the 5 p.m. program Crowd Goes Wild.

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Fox Sports executives are all but taking credit for Olbermann’s return to ESPN. “I don’t know if Keith Olbermann would be back if Fox Sports Live [the network’s 11 p.m. show that will go head-to-head with Olbermann] or Fox Sports 1 did not exist,” Fox Sports executive vp Scott Ackerson told reporters during a conference call July 25. David Hill, the outspoken former Fox Sports chief who now is charged with righting American Idol, among his other 21st Century Fox duties, has said that FS1 will be the fun alternative to ESPN; “jock-ularity” is the catchall he’s coined to describe the network’s tone.

Skipper brushes off the boasting and the horse-race analogies.

“It’s just positioning. It has no basis in actuality,” he says. “Our position is authority and personality. The personality gives you plenty of license to have fun. You’re going to need authority when you have A-Rod and 12 other players suspended. If all you’re going to do is have fun, I’m not quite sure how you’re going to handle Johnny Manziel or a scandal at Penn State. The sports world is large and complex and requires lots of tones and abilities. I think their position is fairly limiting, and I think it’s inaccurate to suggest that we’re the boring old dreadful storm troopers.”

Skipper’s tenure as president of ESPN, which began in January 2012 when he took over from longtime chief George Bodenheimer, has seen multiple out-of-the-box personnel moves, such as securing statistician and author Nate Silver in a deal that includes Silver’s well-trafficked FiveThirtyEight.com.

“I’m getting a lot of, ‘Gee, with Nate Silver and Keith Olbermann, does this portend some sort of shift?’ ” notes Skipper, adding that ESPN has a history of working with original thinkers, including David Halberstam, the Pulitzer-winning journalist covering civil rights, foreign policy and sports; Ralph Wiley, sports journalist and literary collaborator to Spike Lee; and Hunter S. Thompson. “I’m very happy to have [Silver and Olbermann]; it does portend that we’re kind of open for business with smart guys.”

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“The last time I wrote on a chalkboard was probably seventh grade,” says Olbermann.

It is Wednesday night, Aug. 7, and Olbermann, Horowitz and about a dozen others are jammed into a small studio in Chinatown for a promotional shoot. Two prop guys wheel a chalkboard onto the black seamless backdrop. Director Darryl Mascarenhas wants Olbermann to write on the board, though he acknowledges verisimilitude would call for a white board, which typically is found in newsrooms and coaches’ offices. Mascarenhas suggests Olbermann scratch out a field play with Xs and Os. Olbermann suggests a nightly rundown for his show. As he approaches the chalkboard, the image of Bart Simpson repeatedly scrawling out an admonishment during after-school detention comes to mind. “What do you want him to write?” deadpans Horowitz. ” ‘I will respect authority. I will respect authority. I will respect authority.’ “

Olbermann cracks a small smile. Later, when asked why he thinks he has a reputation for being a little hard on the furniture, he reasons: “I never took seriously the idea of deference [to management] just because they were my employers. It’s like, ‘Well, but if you have the wrong idea and I have the right one, what difference does it make where it came from?’ “