Keith Olbermann

Based on Wikipedia: Keith Olbermann

The Man Who Couldn't Stop Burning Bridges

Keith Olbermann has been fired from nearly every major network in American broadcasting. Sometimes twice from the same one. He's been called crazy by Rupert Murdoch, suspended for insulting college students on Twitter, and once left ESPN after calling their headquarters a "Godforsaken place" on national television. And yet, somehow, he keeps getting hired back.

This is the story of a broadcaster who turned bridge-burning into an art form—and whose talent was so undeniable that networks kept building new bridges just so he could set them ablaze.

A Baseball Kid from Westchester

Born in New York City on January 27, 1959, Olbermann grew up in Hastings-on-Hudson, a small village in Westchester County about twenty miles north of Manhattan. His mother Marie was a preschool teacher and a lifelong Yankees fan. His father Theodore worked as a commercial architect. The family was German-American and raised Keith and his younger sister Jenna in the Unitarian tradition—a liberal Protestant denomination known for welcoming skeptics and freethinkers.

His mother's passion for baseball proved contagious. By his teenage years, Olbermann wasn't just watching the sport—he was writing about it for baseball card collecting magazines. This was the mid-1970s, when trading cards were experiencing a renaissance among collectors who were beginning to treat them as investments rather than bubble gum premiums. A 1979 reference book called the Sports Collectors Bible, written by the legendary boxing writer Bert Sugar, mentioned the young Olbermann by name. He was already becoming known in hobbyist circles before he'd finished high school.

Olbermann attended the Hackley School, an elite preparatory academy in nearby Tarrytown that feeds students into Ivy League universities. There he discovered something that would define his life even more than baseball: broadcasting. He started calling play-by-play for the school's radio station, WHTR. The combination of sports knowledge and verbal performance clicked immediately.

He graduated from Hackley in 1975 and enrolled at Cornell University at just sixteen years old. At Cornell's student-run commercial radio station, WVBR, he became sports director—not bad for a teenager surrounded by upperclassmen. He graduated in 1979 with a degree in communication from the College of Agriculture and Life Sciences, an unusual home for a broadcasting major but one that reflects Cornell's quirky land-grant heritage.

The ESPN Years: Making SportsCenter Cool

Olbermann's early career followed the standard trajectory for ambitious young broadcasters: local stations, wire services, small networks. He worked for United Press International and the RKO Radio Network before landing at CNN in 1981, when the cable news pioneer was still finding its footing. He covered the 1980 Winter Olympics at Lake Placid, including the "Miracle on Ice"—the improbable victory of the American hockey team over the Soviet Union that became one of the most celebrated moments in sports history.

Through the 1980s, he bounced between radio and television in New York, Boston, and Los Angeles. His work in California earned him eleven Golden Mike Awards and the California Associated Press named him best sportscaster three times. But the job that would make him famous was waiting in Bristol, Connecticut.

ESPN hired Olbermann in 1992 to anchor SportsCenter, the network's flagship highlights show. What happened next transformed sports television.

Paired with Dan Patrick at the eleven o'clock hour, Olbermann helped reinvent what a sports broadcast could be. The two anchors brought wit, irony, and pop culture references to what had traditionally been a straightforward recitation of scores and highlights. They coined catchphrases. They made obscure jokes. They treated viewers like they were in on something. SportsCenter became appointment television for a generation of fans who wanted their sports served with a side of sophistication.

The partnership worked because the two men had complementary styles. Patrick was the laid-back straight man; Olbermann was the verbose intellectual always ready with an elaborate reference. In 1995, Olbermann won a Cable ACE Award for Best Sportscaster—these were the Emmys of cable television before the Academy of Television Arts and Sciences absorbed cable into its main awards.

The duo later wrote a book together called The Big Show, documenting their time at SportsCenter. Olbermann has also claimed that the short-lived ABC comedy-drama Sports Night, created by Aaron Sorkin, was based on their experience at the show. Given that ABC and ESPN have been under the same corporate umbrella since 1985, the connection seems plausible.

But Olbermann's time at ESPN also revealed the personality trait that would define his career: an inability to coexist peacefully with management.

Bridge Number One Goes Up in Flames

Early in 1997, Olbermann made an unauthorized appearance on The Daily Show, then hosted by his former ESPN colleague Craig Kilborn. During the appearance, he called Bristol, Connecticut—ESPN's headquarters—a "Godforsaken place." ESPN suspended him for two weeks.

Later that year, he left ESPN entirely under circumstances that remained murky but clearly acrimonious. The network's management was furious. Olbermann was unrepentant. For the next decade, the two sides engaged in a cold war of slights and snubs.

When ESPN celebrated its twenty-fifth anniversary in 2004 with a "Reunion Week" that brought back former anchors to the SportsCenter set, Olbermann was conspicuously absent. Craig Kilborn was invited. Charley Steiner was invited. The man who had arguably done more than anyone to make SportsCenter culturally relevant was not.

In a 2002 essay for Salon titled "Mea Culpa," Olbermann offered a partial explanation. "I couldn't handle the pressure of working in daily long-form television," he wrote, "and what was worse, I didn't know I couldn't handle it." He recounted how his former bosses had once told him he had "too much backbone"—a claim that, he noted, was literally true. Olbermann has six lumbar vertebrae instead of the normal five, an anatomical quirk that causes chronic back pain.

It would take years before ESPN and Olbermann reconciled, and even then, the peace was always fragile.

The Fox Sports Interlude

After leaving ESPN, Olbermann landed at Fox Sports Net in 1999. The fledgling network was trying to challenge ESPN's dominance with its own nightly highlights show, Fox Sports News Primetime. They made Olbermann the star anchor.

The show failed to dent SportsCenter's ratings, and Olbermann eventually transitioned to a weekly Sunday evening program called The Keith Olbermann Evening News, where he served as both anchor and executive producer. He hosted the 2000 World Series for Fox Broadcasting and called the network's baseball Game of the Week. He even made ten guest appearances on Hollywood Squares in the summer of 1999—a gig that says something about his comfort level in front of cameras and his willingness to embrace the absurd.

But Fox Sports ended the way ESPN had: badly.

According to Olbermann, he was demoted after asking for a reduction in duties for health reasons. Then, in 2001, he was fired after reporting on rumors that Rupert Murdoch—whose News Corporation owned Fox—was planning to sell the Los Angeles Dodgers. Olbermann called the demotion "blackmail."

Murdoch's response was characteristically blunt. Asked about Olbermann, the media mogul said simply: "I fired him. He's crazy."

Olbermann got in the last word, as he usually does. In 2004, he dismissed his time at Fox: "Fox Sports was an infant trying to stand [in comparison to ESPN], but on the broadcast side there was no comparison—ESPN was the bush leagues."

The Pivot to Politics

After Fox Sports, Olbermann returned briefly to radio, reviving segments originally created by the legendary Howard Cosell. But his career was about to take an unexpected turn—from sports to politics.

In 2003, MSNBC gave Olbermann his own show. Countdown with Keith Olbermann debuted on March 31, taking over the eight o'clock evening slot that had previously been held by Phil Donahue. The format was straightforward: rank the five biggest news stories of the day and count down from fifth to first, with the most important story theoretically saved for last.

In practice, the show was something else entirely. Olbermann brought his ESPN style—the verbal flourishes, the obscure references, the barely concealed contempt for anyone he considered an intellectual inferior—to political commentary. And he found a target-rich environment.

The show launched just as the United States was invading Iraq. President George W. Bush had declared the end of "major combat operations" under a banner reading "Mission Accomplished" on May 1, 2003. For the remaining years of the Bush presidency, Olbermann closed every show by announcing how many days had passed since that declaration—a running counter that highlighted the gap between the administration's rhetoric and the grinding reality of an ongoing war.

He would then crumple up his notes, throw them at the camera, and sign off with "Good night and good luck"—the famous closing line of Edward R. Murrow, the CBS newsman who had helped bring down Senator Joseph McCarthy in the 1950s. Olbermann acknowledged the homage was "presumptuous" and a "feeble tribute," but he kept doing it anyway.

Special Comments and Worst Persons

Countdown developed several signature segments that became lightning rods for both fans and critics.

The "Special Comment" was Olbermann's editorial response to events he found particularly outrageous. These monologues could run for ten minutes or more—an eternity in cable news—and they pulled no punches. Olbermann excoriated the Bush administration, conservative commentators, and anyone else he felt deserved public condemnation. The segments were theatrical, verbose, and unabashedly partisan. They also drew enormous viewership.

"Worst Person in the World" was a lighter feature that named and shamed three people each night for various offenses. The tone was satirical, but the targets were real, and being named "Worst Person" by Olbermann became a badge of honor among some conservatives who considered the segment proof of liberal media bias.

Critics accused Olbermann of creating an "echo chamber" where he only interviewed guests who agreed with him. Howard Rosenberg, then the television critic for the Los Angeles Times, wrote that "Countdown is more or less an echo chamber in which Olbermann and like-minded bobbleheads nod at each other."

Olbermann rejected the "liberal" label that was constantly applied to him. "I'm not a liberal," he would say. "I'm an American." The distinction seemed meaningful to him, even if it struck many observers as semantic gymnastics.

The Label Question

Was Keith Olbermann liberal? The question gets at something fundamental about American political media.

By any conventional measure, his views aligned with the Democratic Party and the progressive movement. He opposed the Iraq War. He criticized the Bush administration relentlessly. He advocated for healthcare reform and against corporate influence in politics. These are liberal positions in the American context.

But Olbermann seemed to object to the tribal implications of the label. Calling yourself a liberal, in his view, suggested you were part of a team, bound by ideological loyalty. He preferred to see himself as an independent truth-teller who happened to reach conclusions that aligned with the left. Whether this distinction was meaningful or merely self-flattering depends on your perspective.

The opposite of Olbermann's approach would be someone like a beat reporter who strives for neutrality, presenting facts without editorial judgment and letting readers draw their own conclusions. Olbermann had no interest in that model. He believed some things were simply wrong—factually, morally, or both—and that a journalist had an obligation to say so clearly.

This put him in the tradition of advocacy journalism, which has a long history in America but fell out of fashion during the twentieth century's brief experiment with "objective" news coverage. By the time Olbermann launched Countdown, that experiment was already collapsing. Fox News had demonstrated that partisan commentary could draw massive audiences. MSNBC was positioning itself as Fox's liberal counterweight. Olbermann was their answer to Bill O'Reilly.

The MSNBC Breakup

In February 2007, MSNBC announced that Olbermann had signed a four-year contract extension. He would continue hosting Countdown, produce occasional specials for NBC, and contribute essays to NBC Nightly News with Brian Williams. He also served as co-anchor for MSNBC's coverage of major news events, including the death of Tim Russert in June 2008.

During the 2008 presidential election, Olbermann co-anchored MSNBC's coverage alongside Chris Matthews. But the arrangement proved contentious. Both men were opinionated personalities who struggled to maintain even a pretense of neutrality during the historic Obama-McCain race. In September 2008, MSNBC replaced them with David Gregory after complaints that their commentary had become too partisan for anchor duties.

Olbermann remained at MSNBC until January 2011, when he abruptly departed. The circumstances, once again, were murky. Olbermann's final show gave no indication that it would be his last. He simply signed off, and the network announced he was gone.

Current TV, Round Three at ESPN, and YouTube

Olbermann's post-MSNBC career became a dizzying carousel of departures and returns.

From 2011 to 2012, he served as chief news officer at Current TV, a small cable network co-founded by Al Gore. He launched another version of Countdown there, but the relationship quickly soured. He was fired in March 2012.

In 2013, ESPN—the network he had left in such spectacular fashion sixteen years earlier—brought him back for a late-afternoon show on ESPN2. The program, called simply Olbermann, was supposed to focus on sports but gave him latitude to discuss "pop culture and current events." He claimed he didn't intend to use the political opening, but given his history, the promise seemed optimistic.

The peace lasted until 2015, when Olbermann was suspended after a Twitter exchange with Penn State University students. The controversy centered on THON, Penn State's annual dance marathon that raises money for pediatric cancer research. It's the largest student-run philanthropy in the world, having raised over $160 million since 1977. Whatever triggered the exchange, Olbermann called Penn State students "pitiful" and added: "I'd like to thank the students and alums of Penn State for proving my point about the mediocrity of their education and ethics."

He apologized on air when he returned, but the damage was done. ESPN announced in July 2015 that the network was moving "in another direction." Another bridge burned.

Olbermann returned to politics with a web series for GQ magazine covering the 2016 presidential election. Originally called The Closer, it was renamed The Resistance after Donald Trump's victory. The show ran until November 2017.

In January 2018, ESPN hired him back again—his third stint at the network—for occasional SportsCenter commentaries and some baseball play-by-play work. In October 2020, he resigned to launch a political commentary program on his YouTube channel. In August 2022, he relaunched Countdown as a daily podcast with iHeartRadio.

The James Thurber Connection

One of the more unexpected elements of Olbermann's broadcasting career is his devotion to James Thurber, the mid-twentieth-century humorist and New Yorker cartoonist. On his current podcast, Olbermann regularly reads from Thurber's works—short stories, essays, and fables that combine gentle absurdism with sharp observation of human folly.

Thurber is an interesting choice for a broadcaster known for righteous anger. His humor was subtle, often self-deprecating, and rarely political. But perhaps that's the point. Thurber provides a counterweight to the fury, a reminder that the world is often ridiculous rather than evil, and that the appropriate response to absurdity is sometimes laughter rather than outrage.

Or perhaps Olbermann simply loves good writing and wants to share it. Not everything requires a deeper explanation.

An Extra Vertebra

That detail about Olbermann having six lumbar vertebrae instead of five is worth pausing on. Most humans have five bones in the lower section of the spine. Having six is uncommon but not rare—it occurs in perhaps one to five percent of the population. The condition, called lumbarization, typically causes no problems but can contribute to lower back pain and complications if surgery is ever required in the area.

Olbermann has mentioned his chronic back pain as a factor in some of his career difficulties, including his request for reduced duties at Fox Sports that allegedly led to his demotion. It's a reminder that behind the combative persona is a physical human being dealing with physical limitations—something easy to forget when watching someone perform on television.

The Pattern

What do you make of a career like Keith Olbermann's? He's been hired by every major sports and news network in America, often multiple times. He's been fired or departed acrimoniously from most of them. He's won awards and attracted huge audiences. He's also been called crazy by one of the most powerful media executives in the world and suspended for insulting college students on social media.

One interpretation is that Olbermann is simply too talented to ignore and too difficult to employ. His verbal abilities are genuinely exceptional—the elaborate sentences, the historical references, the theatrical delivery. When he's on, he's compelling television. But that talent comes packaged with a personality that seems constitutionally incapable of institutional harmony.

Another interpretation is that Olbermann represents something about American media itself. The same industry that rewards confrontation and controversy also demands that its employees play nice with management. The contradiction is built into the system. Someone like Olbermann exposes it by being exactly what the audience wants and exactly what the executives can't handle.

A third interpretation is simpler: some people are just difficult, and Olbermann is one of them. No deeper meaning required.

The Current Chapter

As of his most recent incarnation, Olbermann hosts a daily podcast called Countdown with Keith Olbermann through iHeartRadio. The show features his trademark segments—the Special Comments, the Worst Persons in the World—along with the Thurber readings that have become a signature of his later career.

He's sixty-six years old now. His hair has grayed but his opinions haven't softened. Whether you find him brilliant or insufferable—and there seem to be very few people who feel anything in between—Keith Olbermann remains exactly who he has always been: a man with too many words, too many enemies, and just enough talent to keep finding microphones to speak into.

The bridges keep burning. The networks keep building new ones. And somewhere in the background, James Thurber's gentle absurdism provides a quiet counterpoint to all that righteous fire.