The Confessions of Keith Olbermann

Issue 22 Cover Keith Olbermann
Wesley Mann

Keith Olbermann breaks his silence on his messy departure from MSNBC and discusses his return to news on Current TV.

FULL COVER STORY: The Confessions of Keith Olbermann

Now with a bigger paycheck but a smaller network, the stand-up-to-management bad boy unloads for the first time about MSNBC, Jeff Zucker, why he's not talking to Rachel Maddow and his plan for Countdown 2.0 on Current TV.

Keith Olbermann hobbles into the cavernous Highline Studios in Manhattan's Meatpacking district. A black collapsible cane in his left hand, he carefully picks through jumbles of wires and gingerly sidesteps an equipment cart. A brace on his left foot protects a healing second metatarsal, the long bone in the foot.

Asked how he was injured, he jokes, "I broke it on Glenn Beck's shiny metal ass." PHOTOS: Keith Olbermann's famous feuds

Actually, he explains, he fractured it because he was running in "five toes." The froglike slippers are designed to deepen one's connection to the earth. But they should not be worn during impact exercise by anyone more than 175 pounds. ("I haven't been 175 pounds since high school," the 6-foot-3½-inch anchor admits.)

Yet on this day, TV news' predominant left-leaner -- without a cable platform since he abruptly announced on-air Jan. 21 that he was quitting MSNBC that very night -- is still a two-ton gorilla. Dressed in his trademark suit (he prefers Hickey Freeman), he is here to film promos for Countdown With Keith Olbermann, the Current TV version of his former MSNBC program that will bow June 20 at 8 p.m. It is the same time slot he occupied on MSNBC for nearly eight years -- propelling the network from also-ran to contender and primetime counterweight to the conservative firebrands on Fox News. These days, Lawrence O'Donnell, who was known to fill in on Countdown when Olbermann was out, is hosting his own show in the time slot (and pulling in comparable numbers).

"I don't think my former employers thought this was going to turn out quite this way. I just don't think they thought they'd be in competition with me, so fast or at all," says Olbermann, 52, who can't resist adding, "and my understanding is this has left a certain tension over there."

The promo he's filming -- called "Keith-on-Keith" -- has him interviewing himself. It is an id-superego volley that is equal parts grenade launcher and bomb defuser, letting Olbermann lambaste familiar enemies while deflecting adjectives that have adhered to him during a 30-year career in television.

An Olbermann stand-in sits off-camera firing questions at the real one behind the desk.

Q: "OK, Keith, why Current?"

A: "Like you don't know the answer to that."

Q: "Why don't conservatives have a sense of humor?"

A: "Who built the pyramids? These are unanswerable questions."

Q: "What do you say to critics who find you smug?"

A: "I'm not smug. I just never learned how to bullshit very well."

Q: "Do you ever admit you're wrong?"

A: "On occasion."

Q: "How many times have you been fired?"

A: "I was fired once, by Rupert Murdoch. And it was the happiest day of my life."

The director yells: "Cut!"

Olbermann inquires: "What about the spit take?"

A production assistant springs into action, bringing him a mug filled with water.

"What question do you want to prompt the spit take?" asks the director.

Says Olbermann, "Is it true that when you were at Cornell you dated Ann Coulter?"


Two and a half weeks after he and MSNBC parted ways -- a bombshell that launched a firestorm of tweets, anger and, of course, right-wing cheers -- Olbermann announced a new deal with Current TV, the company founded nearly six years ago by recovering politicians Al Gore and Joel Hyatt (a 1994 Democratic Senate candidate from Ohio and longtime political adviser to the late Howard Metzenbaum, his father-in-law). Olbermann's $7 million-a-year MSNBC contract, which had two years left on it, forbids him from going to any competing cable news outlet. Online was an option (Olbermann spoke to Yahoo), as were sports outlets (he spent 5½ tumultuous years at ESPN and another couple doing an ESPN Radio show with his SportsCenter co-anchor Dan Patrick). The announcement of his Current TV gig came as a surprise largely because one of TV's best-known personalities was heading to one of TV's least-watched channels. (Current's ratings are second-lowest only to ESPN Classic, which focuses on decades-old games). "It's been fascinating to see the assumption that this is some sort of bizarre move for me," he says. "I have achieved what I wanted to achieve. I'm better off at some sort of independent place where they not only like what I produce but also trust me to be the one to produce it."

But while Current touts independence from the competing interests that news organizations that are part of international conglomerates face, the appointment of the oft-polarizing figure also cements a partisan identity.

"We see ourselves as the only independent news and information channel on television," says Gore. "The point of view expressed by Keith Olbermann is one that I share more often than not. When he says something that I don't agree with and somebody asks me about it, I'm happy to say I disagree. But I will defend his right to speak independently and passionately."

Still, Olbermann isn't at 30 Rock anymore (or even on the ESPN campus in Bristol, Conn., where he got himself in hot water more than once). His Current show will originate from a studio in a decidedly unglamorous building on Manhattan's West 33rd Street between 10th and 11th avenues; Olbermann calls it "the fortress of isolation." As he did at MSNBC, Olbermann will serve as the leadoff hitter for a primetime lineup that eventually will include at least one more commentary show and event coverage including the 2012 presidential election. His Current show will look much like the MSNBC show, with multiple stories and a "worst persons" segment. He also reveals in our conversations that he has recruited as his primary substitute anchor David Shuster -- who last year was suspended from MSNBC when it came out that he had taped a pilot at rival CNN.

Olbermann has signed a stable of contributors including Rolling Stone's Matt Taibbi, Daily Kos founder Markos Moulitsas, comedian Richard Lewis and filmmakers Michael Moore and Ken Burns. Current is not paying many of them -- at least not in the traditional sense. Moore will be compensated via a donation to charity. Burns declined compensation. Moulitsas, who will appear regularly on Countdown, is receiving what he characterized as a "token amount." "I'm not a big fan of being on television," says Moulitsas. "But there are people I appreciate and so I like to do their shows, and Keith is one of those people."

In recent weeks, Olbermann hired David Sarosi -- who produced the "worst persons" segments on MSNBC -- as executive producer. Senior producers include Leslie Bella-Henry, who produced for Lou Dobbs at CNN; Bob Lilly, who worked with Olbermann at MSNBC; and Aaron Volkman, whom Olbermann poached from MLB Network. "I'm a natural management guy," Olbermann says. "I had forgotten that. And I forgot how much I hate it."

But if some of his contributors are doing this on a shoestring, Olbermann is not. He is drawing a salary of $10 million a year, says a source. (Current TV disputes the figure but adds it does not "disclose confidential, contractual details.") Meanwhile, Olbermann will continue to collect his MSNBC wage for another year and a half. At Current, where he is also chief news officer with an equity stake in the company, he is No. 4 on the corporate ladder behind Gore, Hyatt and CEO Mark Rosenthal, an MTV veteran who was on Current's board before being tapped in 2009 to re-invent the network's programming. Olbermann's equity has the potential to inflate his payday exponentially over the life of his five-year deal. Sources say that Countdown will cost about $15 million a year to produce, and the network is spending another $5 million upfront on marketing. All this for a cable channel that is only in 60 million homes in channel Siberia (versus MSNBC's 95 million with prime positioning). Says Rosenthal, "We will spend the money we need to spend to make Keith into even more of a household name than he already is."

"If they're trying to unseat MSNBC as the progressive voice at 8 o'clock every night, they're behind the eight ball when they start," says a veteran TV producer who has worked with Olbermann off and on for two decades. "It is kind of a David and Goliath story. But David wins every once in a while."

Olbermann believes he can lift Current out of obscurity. But for all the lip service paid to DVR-empowered viewers -- "We're not asking people to pass a bar exam to watch the show," says Olbermann. "We're asking them to remember three numbers" -- location still matters. "The three most important things in cable are carriage, carriage and carriage," notes Larry Gerbrandt, principal at Media Valuation Partners. "Programming comes in at No. 4. If you don't have carriage, programming literally doesn't matter."

Current executives already are having conversations with distributors. And in the run-up to launch, Current is pressing all its promotional levers: print and online ads in ideologically congruent periodicals (The New Yorker, The Nation, The New York Times) and websites (Talking Points Memo, Daily Kos, Politico); national and local TV spots; and a robust in-house TV and online promotional campaign led by marketing chief Kent Rees. Gore, Hyatt, Rosenthal and Olbermann also will make a swing through Chicago for a private schmooze with affiliates and advertisers at the Cable Show, the annual media confab that runs June 14 to 16. "Distributors who have not yet become affiliates of Current will have to face a lot of subscribers who will say, 'Where can we get Keith Olbermann, and how quickly can we get him?' " says Rosenthal.

No one doubts Olbermann will attract attention -- good and bad. Even on hiatus, he remained a hot topic, guided by what he would likely characterize as his moral compass. Since his last broadcast, he engaged in a Twitter war with ESPN columnist Bill Simmons, who has 1.4 million Twitter followers, nearly five times as many as Olbermann, over a joke Simmons made comparing the John F. Kennedy assassination to the L.A. Lakers' playoff flameout. Both men are featured prominently in James Andrew Miller and Tom Shales' ESPN tell-all Those Guys Have All the Fun, where, it seems, ESPN employees lined up to trash their former marquee star. ESPN anchor Bob Ley: "We felt not so much relief when Keith left as unrestrained f--ing joy." ESPN chairman Herb Granath: "I was enraged by Olbermann. Guys like that just piss me off … because there's no loyalty. It's just me, me, me. There was no choice but to get rid of him."

Olbermann is working his way through the 784-page tome. "I naturally read the parts about me first to see if there were any forest fires. There were no forest fires. There are some funny things in it," he says, adding, "Honestly, hearing which executive thinks he was most responsible for the success of the place is probably not going to interest people who are picking up the book to find out how big of a jackass I am. Was I not a big enough jackass? Do I need to go back and jackass some more?"

But Olbermann has larger targets than ESPN (from whose campus it's rumored he is banned) -- like longtime "worst person" staple Murdoch. On Twitter, he attacked Murdoch after News Corp. dropped Current on Sky Italia. Olbermann excoriated Murdoch's "evil empire" and later vowed a fight: "Rupert, you have been warned." Olbermann also launched the FOK News Channel website and Twitter feed (FOK is an acronym for "Friends of Keith," and the logo is designed to ape Fox News Channel's "patriotic" red, white and blue emblem). The FOK site now redirects to Current's Countdown page, where Olbermann has been posting videos including "worst persons" segments -- which until last week he was recording in the den of his Upper East Side apartment.

But these recent playground skirmishes pale in comparison to his tenure at MSNBC. Olbermann's departure was the culmination of years of simmering tensions. Indeed, he admits the split was so bad he still has not spoken to onetime mentee Rachel Maddow: "There were lots of people who were forced to choose sides. And particularly in Rachel's case, I didn't want to add to the pressure on her already. The last thing I need to do is be calling her up and saying, 'How's that Michael Steele working out for you?' [He signed to NBC as a political analyst on May 23.] Which is exactly what I would do if I were in the office."

He left the network once before, in 1998 after a brief stint. NBC sold his contract to Fox Sports Net, where he lasted until 2001, when Murdoch fired him for reporting that News Corp. was looking to unload the Los Angeles Dodgers, says Olbermann.

This time, his tenure at MSNBC was longer and wildly successful. In 2003, its first year on MSNBC, Countdown averaged 350,000 viewers. The show peaked at 1.3 million viewers in 2007 -- during the wild and woolly 2008 presidential campaigns. When Olbermann left MSNBC in January, his show was averaging more than 1 million viewers. (O'Donnell's Last Word finished May averaging 1 million viewers.) But the scorched-earth theme is a recurring one.

"Every job he has ever had, he and the person he's working for end up hating each other," says a former MSNBC colleague who maintained a good relationship with Olbermann. "He grows more and more frustrated with not having complete autonomy until it becomes unworkable."

Still, Olbermann is undeniably smart and an engaging TV presence and thus has been irresistible to many a media CEO. In 2005, before CBS News wooed Katie Couric to the network, CBS Corp. president and CEO Leslie Moonves and former CBS News president Andrew Heyward spent two hours at Olbermann's Central Park South apartment exploring the possibility of his joining the news division as CBS Evening News anchor, according to Olbermann. Moonves, says Olbermann, "had that lust-for-talent look in his eyes. I saw it."

When asked about the meeting recently, Moonves visibly bristles: "It was an hour, and it wasn't for the main [anchor] job."

In late 2006 to early 2007, former CNN president Jon Klein also tried to recruit Olbermann for the 8 p.m. slot. Says Klein: "I'm not alone in thinking Keith is a natural, gifted television performer who creates a sense of must-watch. And that is rare." On the CNN opportunity, Olbermann muses: "What would have happened if I had gone over to CNN and taken my then-nascent guest host Rachel Maddow with me? Different world."


With a presidential campaign that delivered more drama -- and personalities -- than any in recent memory, 2008 should have been a banner year for Olbermann. But the summer began with a terrible shock. NBC News' Tim Russert, someone Olbermann viewed as a friend, died suddenly June 13. Olbermann says it was a turning point for him at MSNBC, where Russert was long one of his network allies. NBC's Washington bureau chief and host of Meet the Press had a prosecutorial mind but a knack for diplomacy that, it's safe to say, eludes Olbermann. "Tim knew how to play them," he says. "He managed to do that with every faction, with every complaint from the Republican side, with every complaint from the Democratic side, with every complaint from a staffer. He knew how to turn it into a conversation that ended in laughter. Tim, for the noblest of causes, could bullshit very well. And I admired him for it. It seems to sap my creative voice."

Then, in September, Olbermann and Chris Matthews were bumped from lead anchors to analysts on MSNBC's election coverage, underscoring the network's identity crisis as a news organization whose biggest stars were openly partisan.

In 2009, Olbermann was discovering he had few allies left at NBC and then-corporate parent General Electric. His pointed jabs at Fox News, its executives and personalities -- especially Bill O'Reilly and O'Reilly's crusade against GE chairman and CEO Jeffrey Immelt -- prompted then-NBCUniversal CEO Jeff Zucker and News Corp. executive vp Gary Ginsberg to attempt to broker a detente. But, say those who have worked with Olbermann, such "tweaking" and Olbermann's "inability to stop going after Fox even when corporate people asked him to" only ratcheted up the tension. Says one former MSNBC executive: "He's the kind of person that the higher the rank of the person who asks him to stop doing something, the less likely he is to comply. He has a pretty serious authority issue."

On his reputation, Olbermann says: "I'm difficult for management. That's why I have the reputation because nobody challenges management." He adds that his run-ins are simply out of good conscience: "I stand up to people. I do not believe that simply because I signed a contract that that gives people the right to make [unilateral] decisions. As part of the process by which you hire me, you hire me. You just don't hire an hour of me to do a performance."

The following summer, Olbermann was yanked from NBC's Sunday Night Football preshow, a move that clearly still irks him. Until then, he had a hand in NBC Sports' football coverage dating to 2007. Company executives said he was removed from Football Night in America because it interfered with his day job on Countdown. But internally, he was  criticized for lacing his commentary with political references, a no-no in the apolitical arena of televised sports. And Olbermann contends Zucker was personally punishing him.

"You are not allowed to disagree with him, or he will exact vengeance," says Olbermann.

The particular transgression that got him booted? Olbermann says he was caught gossiping about Zucker's fate at the company after Comcast had announced its bid to merge with NBCUniversal. "There was a lot of speculation about what would happen," he says. "One surprisingly accurate bit of speculation on every floor of the building was, 'I betcha they don't keep Jeff.' And apparently he heard that I had said this. I was there, and I was a convenient punching bag, and everybody would believe everything they said about me. And so off I went." (Zucker did not respond to repeated e-mails seeking comment.)

Shortly thereafter, Olbermann parted ways with longtime agent Jean Sage -- with him since he was a 24-year-old sports wunderkind -- in favor of Hollywood agency ICM and Ted Chervin and Nick Kahn. Olbermann characterizes the breakup as mutual.

"The amount of interference that I needed run on my behalf exceeded Jean's capacity," he says. "And she agreed with me. When you get a little bit bigger than that, you've got to have a bunch of sharks."

Among colleagues at MSNBC, Olbermann developed a particular reputation. His blistering sarcasm and habit of icing people by simply not communicating could leave some devastated. "I have sometimes been curt or standoffish with people who work below me on the food chain," he admits. "But it's usually an issue of, 'I have no time.' It's like: 'I've got to get on the air. Where is this? Help me! Jesus, just get me the tape!' It's not personal. I don't yell at people -- downward. I yell at people upward. It's not always OK. But the point is that's what will get you the reputation faster than anything else."

Rick Kaplan, president of MSNBC during Countdown's early days, occasionally butted heads with Olbermann. But, he says, "If he were so horrible to work for, I would have had someone come to me and ask to be taken off his show. And in the [two and a half] years that I was there, not one person ever did. They knew he was prickly. But he was also incredibly smart and talented and loyal. And his staff loved him."

Still, Olbermann's behavior was erratic, a little careless, in the months preceding his exit. He pulled his "worst persons" segment in response to Jon Stewart's Rally to Restore Sanity, begging for civility in news, only to reinstate it three weeks later. More significantly, in November, he was suspended for two days -- a Friday and a Monday -- for not disclosing campaign donations made to three Democratic candidates for Congress (including Gabrielle Giffords, who was shot Jan. 8 in Tucson, Ariz., and is recuperating). "It seemed like this huge thing externally," he says. "Internally, it was like, 'OK, put that on the list.' "

One source who knows Olbermann characterized the campaign donations as the proverbial last straw. "At that point, I think they [MSNBC management] were looking for the straw that would break the camel's back," says this source. "I don't know what's less than a straw, a thread, an eyelash? He apologized. He took a suspension. It wasn't a big amount of money. It wasn't a big newsmaker that he made the donation to. It was a fairly minor infraction. But I think they were looking for some reason to end the relationship." (MSNBC declined comment, though neither side will confirm the reported existence of a non-disparagement pact.)

Olbermann's former MSNBC colleague Joe Scarborough endured his own suspension for donations to Republican candidates and seemed to suggest recently on-air that MSNBC management, like their Fox News counterparts, also had warned hosts not to pour gasoline on the political firestorm that erupted after the Tucson shootings. But in a Countdown special comment days after the shootings, Olbermann tore into Sarah Palin, O'Reilly and Beck, asserting that it was "time to put the guns down" and "put the gun metaphors away permanently." He also offered an apology if his own rhetoric had ever "encouraged violence."

"Frankly, I knew before Gabby Giffords got shot, several weeks beforehand, that the NBC experience was coming to a close," Olbermann says now.

His colleagues at MSNBC might have surmised that his days were numbered. ("I think the smart ones suspected something was up, because every night I was leaving with various objects from my office," he says.) But as Olbermann went on air at 8 p.m. EST on Jan. 21, his staff did not know it was his final broadcast. Olbermann had prepared two endings for the show; one with two readings from James Thurber and another with a Thurber reading and his farewell to viewers.

"As far as anybody knew," says Olbermann. "I was doing the two Thurber stories."

Meanwhile, huddled off-camera at Countdown's Studio 1A-Up, above the Today show's Studio 1A, were Olbermann's representatives (Chervin and Kahn from ICM and Michael Price, Olbermann's manager) and MSNBC president Phil Griffin and an NBC lawyer. As the long 8:30 p.m. midbreak began, a negotiation for Olbermann to be let out of his contract -- a negotiation that had dragged on all week and into Friday evening -- was finally complete.

Olbermann was hoping to tell the staff before the show began, he says, but "once we got past 7 o'clock, I'm not going to hold a staff meeting at seven and say: 'OK, this is the last show everybody. Have a good one. I've got to go over to makeup now. Bye!' "

Olbermann recalls breaking the news to his staff as the commercials rolled: "I said, 'There will be a special announcement that this will be the last show.' That was unfortunately the first time everybody knew about it."

After the broadcast, Olbermann headed to Gramercy Tavern restaurant with his team to celebrate and regroup as the Twitterverse and websites exploded. The next day, a Saturday, Gore called.


Now Olbermann, the ultimate stand-up-to-management bad boy, is management himself. He has to figure out how to do a comparable show to his last one but this time without an international news operation behind him. (Current has become a client of the CBS News affiliate service Newspath, which provides national, international and sports feeds.) While the network has a small cadre of journalists who work for its highly regarded investigative franchise Vanguard, there are no foreign bureaus or Washington correspondents. Olbermann brushes off such logistics. But the fact remains: He is now at a small network, one that he himself characterizes as a "startup." At the promo shoot, when a computer glitch causes a three-minute delay in production, he barks, only half-joking: "Speed it up! This costs money."

But at Current, he may have found in Gore and Hyatt a couple of managers who are willing to let Keith be Keith.

"Keith's problems," says Hyatt, "I think historically stem in part from the confines of being within a huge conglomerate-owned news operation."

His new office is on the second floor above the studio. It overlooks New York's train graveyard. But Olbermann contends it is a better view than the one he had at MSNBC, smack in the media corridor of Manhattan's 6th Avenue. "I like trains," he says. Unable to resist a jab, he adds, "It's better than looking out the window and seeing Fox News."