Still, where some saw a brash breath of fresh air, others saw a self-righteous gasbag. And despite the show’s unprecedented success (Olbermann and Patrick were SportsCenter’s most popular duo), Olbermann was a world-class agitator. He began firing off thousand-word memos to management, lobbying on causes from saner hours for lowly production assistants to profit-sharing for ESPN employees who were helping the network generate billions. Along the way, he won a reputation as a miserable jerk.
“Of all the people I’ve known inside and outside of the business, he was the unhappiest,” recalls a SportsCenter staffer. “Sometimes, at the end of the night, I’d leave early just so I wouldn’t have to give him a ride home. And it wasn’t out of my way.”
In 1997, Walsh allowed Olbermann’s contract to expire, and Olbermann escaped to his NBC and MSNBC gigs. “I’d always wanted to do news,” says Olbermann. “But every time I had a chance to leave sports for news, I’d find a reason not to do it.”
In quintessential Olbermann form, he was ready to quit the show before it started. That Labor Day weekend found him in the Hamptons along with then–Today-show producer Jeff Zucker and Phil Griffin, a longtime Olbermann friend and soon-to-be producer of his MSNBC show. The weekend was going well until news came in that Princess Diana’s limo had crashed inside a Paris tunnel. According to a source familiar with the situation, Zucker and Griffin began dialing their cell phones furiously while Olbermann panicked, alternately chanting, “We’ve got blood on our hands” and “I’m not going to be able to do the show.” (Olbermann denies this characterization.)
Ultimately, Olbermann went ahead with the program. The Big Show was essentially a free-ranging forum for Olbermann’s edgy, quick-witted commentary and polymathic interests. But when the Monica Lewinsky scandal broke, the show morphed into an all-Monica-all-the-time format—a development Olbermann couldn’t stomach. “All the yelling on the show reminded me of a part of my childhood that I didn’t want to relive,” recalls Olbermann. “I just couldn’t deal with it.”
In May 1998, Olbermann gave the commencement address at Cornell. “There are days now when my line of work makes me ashamed, makes me depressed, makes me cry,” Olbermann told the assembled soon-to-be graduates. “About three weeks ago, I awakened from my stupor on this subject and told my employers that I simply could not continue doing this show about the endless investigation and the investigation of the investigation, and the investigation of the investigation of the investigation.” The speech, naturally, didn’t go over well at MSNBC. Olbermann stayed on through that fall, but in December, his contract was sold to Fox.
Olbermann moved to Los Angeles, doing baseball pregame shows and a quirky Sunday-night news show that was critically acclaimed and universally unwatched. But again, Olbermann was unhappy. He bought a house on the Pacific Coast Highway in Santa Monica, but found it too noisy and moved out after a week and a half. Then he moved into a posh Santa Monica hotel, but eventually left over a billing fight involving $16,000 worth of disputed phone calls. In May 2001, Fox canceled Olbermann’s show and took him off their baseball broadcasts, eight months before his contract was up—with no explanation. In June, Fox bought out the remainder of Olbermann’s deal.
That summer, Olbermann was a man without a broadcast. He moved back to New York, and was working on a novel when he had a dream in which JFK appeared before him on a bus, his head wound dressed with plaster of Paris. In the dream, JFK had just one question for Olbermann: “Why did you leave SportsCenter?” (The novel was never published.) That summer, Olbermann spent hours tending to his baseball-card collection, feuding with the L.A. hotel, and generally nursing grudges against the world. Even longtime friends Patrick and Griffin were at loose ends on how to help their friend.
Then 9/11 happened. “Please don’t say how my life changed on 9/11,” said Olbermann. “I didn’t have some epiphany. It trivializes people who really suffered.”
But something changed. After the towers fell, Olbermann began filing freelance dispatches from Manhattan for an L.A. radio station. They were surprisingly moving and heartfelt. For the first time, Olbermann seemed to have found a purpose.
By 2002, Olbermann was in full rebuild mode, penning a 3,000-word Salon piece, titled “Mea Culpa,” apologizing to ESPN for his years of churlish behavior. Olbermann wrote, “I have lived much of my life assuming much of the responsibility around me and developing a dread of being blamed for things going wrong. Moreover, deep down inside I’ve always believed that everybody around me was qualified and competent, and I wasn’t, and that some day I’d be found out.”