Where did his feelings of inadequacy come from? “My frustration has been over many years of never being able to be an irresponsible kid,” says Olbermann. “I’ve always felt like I was the designated driver 24 hours a day.”
In late 2002, Phil Griffin brought Olbermann back to MSNBC as a guest host on the Jerry Nachman program. With the network foundering in a distant third place to CNN and Fox News, Griffin gambled and gave Olbermann a second chance.
Olbermann has had his bumps in his current gig. It took time for Countdown to find its audience, and Olbermann, despite having significantly mellowed by most accounts, has again had run-ins with colleagues. In December, when Dan Abrams, a former MSNBC talking head and now the network’s general manager, offered praise for Olbermann’s show, Olbermann repaid him for the favor by saying, “I don’t know what Dan has to do with [my show], frankly. We’ve never had a conversation about the direction of the show.” And he once told a viewer via e-mail that MSNBC reporter Rita Cosby is “nice, but dumber than a suitcase of rocks.”
Still, four years in at MSNBC, Olbermann is probably about as happy as he can be. With his newfound success came a fresh contract, reportedly worth $4 million a year, and the promise of prime-time Countdown specials. Once a recurring “Page Six” figure for his dating escapades, Olbermann recently moved in with his girlfriend, Katy Tur. Yes, she’s a 23-year-old 2005 graduate of the University of California, Santa Barbara, but the relationship marks his first attempt at cohabitation. For the moment, anyway, Olbermann seems to have achieved a measure of peace. “It takes some people a long time to find their happiness,” says Olbermann’s friend and producer, Griffin. “Keith has that now.”
At the end of The Candidate, Robert Redford turns toward a crony at his victory party and says, “What do we do now?” Post-2006, Keith Olbermann is facing the same problem. With Bush headed toward irrelevance, Olbermann’s favorite target is passing from the scene. What’s a W. basher to do?
Olbermann insists he’ll slam whoever deserves slamming, and that that strategy will serve him fine. Unlike his sworn enemy, O’Reilly, who proclaims almost nightly how he will use his program to hold presidential candidates accountable, Olbermann is reluctant to say how Countdown will cover the 2008 election. “I hesitate to plan stuff,” says Olbermann. “Then you get away from it being organic.”
Not that Olbermann lacks opinions on the candidates. A few weeks ago, on another ride out to Secaucus, I toss out names like clay pigeons for him to blast down.
Giuliani: “He had a great finish, but the rest of the time he was a schmuck.”
Hillary: “When I interviewed her, she didn’t seem preprogrammed. It was like she had gone to Hillary boot camp: ‘Don’t answer like that. Smack! Answer like this.’ If she doesn’t Alex Rodriguez everything, she may get through.”
Obama: “At the end of our interview last October, he asked me who I thought was going to win the World Series, the Cardinals or the Tigers. I told him the Tigers. And he said, ‘Yeah, I think they’re going to beat them fairly easily.’ At that point, I realized, ‘He’s from Illinois, and downstate Illinois is Cards territory.’ He was willing to pick against the Cardinals on national TV. He’s willing to say, ‘You’re not going to agree with everything I say.’ The politician who can do that is the one who is going to cut through. I don’t think that’s going to be Giuliani. I don’t think it’s Mitt Romney or McCain.”
Earlier, for the sheer sport of it, I had asked him about O’Reilly: “It wasn’t until I left MSNBC in December of ’98 that Bill took second place. Seeing what he did with that and the perversions of television he’s created, I felt bad about it. I might have been able to stop this. It must be like the way Gore or Kerry wake up in the middle of the night thinking, I could have stopped this. I carry that around with me.”
By now we’re at the studio, in a makeup room, and Olbermann starts in on Anderson Cooper. The CNN anchor, Olbermann notes, recently told a Men’s Journal writer that he wouldn’t talk about his private life. “Don’t tell me you don’t want to talk about personal life when you wrote a book about your father’s death and your brother’s death,” says Olbermann. “You can’t move this big mass of personal stuff out for public display, then people ask questions and you say, ‘Oh, no, I didn’t say there was going to be any questions.’ It’s the same thing as the Bush administration saying, ‘We’re going to war, but you really aren’t allowed to know why.’ ”