Olbermann was born January 27, 1959, in New York City, the son of Marie Katherine (née Charbonier), a preschool teacher, and Theodore Olbermann, a commercial architect. He is of German ancestry. Olbermann and his younger sister Jenna (b. 1968), were raised in a Unitarian household in the town of Hastings-on-Hudson in Westchester, New York. He attended the Hackley School, a private Ivy League Preparatory school in nearby Tarrytown.
While at Hackley, Olbermann began his broadcasting career as a play-by-play announcer for WHTR. After graduating from Hackley in 1975, he enrolled at Cornell University at the age of 16. At college Olbermann served as sports director for WVBR, a student-run commercial radio station in Ithaca. Olbermann graduated from Cornell University's College of Agriculture and Life Sciences in 1979 with a BS in communication.
Early in 1997 Olbermann was suspended for two weeks after he made an unauthorized appearance on The Daily Show on Comedy Central with then-host and former ESPN colleague Craig Kilborn. At one point in the show he referred to Bristol, Connecticut (ESPN's headquarters), as a "Godforsaken place". Later that year he abruptly left ESPN under a cloud of controversy, apparently burning his bridges with the network's management; this began a long and drawn-out feud between Olbermann and ESPN. Between 1997 and 2007 incidents between the two sides included Olbermann's publishing an essay on Salon in November 2002 titled "Mea Culpa", in which he stated, "I couldn't handle the pressure of working in daily long-form television, and what was worse, I didn't know I couldn't handle it." The essay told of an instance when his former bosses remarked he had "too much backbone", a claim that is literally true, as Olbermann has six lumbar vertebrae instead of the normal five.
In 2004, Olbermann was not included in ESPN's guest lineup for its 25th anniversary SportsCenter "Reunion Week", which saw Craig Kilborn and Charley Steiner return to the SportsCenter set. In 2007, ten years after Olbermann's departure, in an appearance on the Late Show with David Letterman, he said, "If you burn a bridge, you can possibly build a new bridge, but if there's no river any more, that's a lot of trouble." During the same interview Olbermann stated that he had recently learned that as a result of ESPN's agreeing to let him return to the airwaves on ESPN Radio, he was banned from ESPN's main (Bristol, Connecticut) campus.
According to Olbermann, he was demoted by Fox when he asked for a slight reduction in duties for health reasons, and then was fired from Fox in 2001 after reporting on rumors that Rupert Murdoch, whose News Corporation owns Fox, was planning on selling the Los Angeles Dodgers. Olbermann characterized the demotion as "blackmail." When asked about Olbermann, Murdoch said, "I fired him ... He's crazy." In 2004 Olbermann remarked, "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."
After Olbermann left Fox Sports in 2001, he provided twice-daily sports commentary on the ABC Radio Network, reviving the "Speaking of Sports" and "Speaking of Everything" segments begun by Howard Cosell. In 2005, Olbermann made a return to ESPN Radio when he began co-hosting an hour of the syndicated Dan Patrick Show on ESPN Radio, a tenure that lasted until Patrick left ESPN on August 17, 2007. Olbermann and Patrick referred to this segment as "The Big Show", just as their book was known. Patrick often introduced Olbermann with the tagline "saving the democracy", a nod to his work on Countdown. On April 16, 2007, Olbermann was named co-host of Football Night in America, NBC's NFL pre-game show that precedes their Sunday Night NFL game, a position which reunited him in 2008 with his former SportsCenter co-anchor Dan Patrick. Olbermann left the show prior to the start of the 2010 season.
It was announced on July 17, 2013, that Olbermann would host his own one-hour nightly show on ESPN2. The two-year contract would allow him to deviate from the topic of sports into realms such as "pop culture and current events", as well as politics, which was a right Olbermann claimed he did not intend to exercise.
Olbermann was suspended by ESPN in 2015 for the week following Penn State University's annual philanthropy THON due to a Twitter exchange he had with Penn State supporters. THON is the world's largest student-run philanthropy, raising over $160 million for pediatric cancer research since 1977. In the Twitter exchange, Olbermann stated, "PSU students are pitiful." Later, prior to apologizing, Olbermann stated, "I'd like to thank the students and alums of Penn State for proving my point about the mediocrity of their education and ethics." Olbermann apologized on his program upon his return March 2, but noted, "I'm much more sorry about batting practice [i.e. trolling or cyber bullying]. So for me, batting practice ends."
In July 2015 ESPN announced that it would be Olbermann's last month with the network. ESPN said that it was a "business decision to move in another direction".
Olbermann left MSNBC for Fox Sports Net shortly thereafter. After leaving Fox Sports in 2001, Olbermann returned once more to news journalism. In 2003, his network won an Edward R. Murrow Award for writing on the "Keith Olbermann Speaking of Everything" show. In addition, Olbermann wrote a weekly column for Salon.com from July 2002 until early 2003, worked for CNN as a freelance reporter, and was a fill-in for newscaster Paul Harvey. Olbermann revived his association with MSNBC in 2003 briefly as a substitute host on Nachman and as an anchor for the network's coverage of the war in Iraq.
The first few stories shown were typically oriented toward government, politics, and world events; the segments ranked numbers two and one were typically of a lighter fare than the preceding segments. These lighter stories sometimes involved celebrities, sports, and, regularly and somewhere in the middle, the bizarre, in a segment he called "Oddball." Opinions on each were offered by Olbermann and guests interviewed during the segment. Olbermann had been criticized for only having guests that agree with his perspective. Former Los Angeles Times television critic Howard Rosenberg stated that "Countdown is more or less an echo chamber in which Olbermann and like-minded bobbleheads nod at each other."
On February 16, 2007, MSNBC reported that Olbermann had signed a four-year extension on his contract with MSNBC for Countdown which also provided for his hosting of two Countdown specials a year to be aired on NBC as well as for his occasional contribution of essays on NBC's Nightly News with Brian Williams.
In November 2008, it was announced that Olbermann had signed a four-year contract extension worth an estimated $30 million.
On January 21, 2011, Olbermann announced his departure from MSNBC and that the episode would be the final episode of Countdown. MSNBC issued a statement that it had ended its contract with Olbermann, with no further explanation. Additional reporting in the days immediately following suggested that the negotiations for the end of Olbermann's tenure at MSNBC had begun soon after the end of his suspension.
On February 8, 2011, it was announced that Olbermann had become the chief news officer for the public affairs channel Current TV and would begin hosting a one-hour prime time program on the network at 8 pm Eastern – the same time slot that Countdown had been on MSNBC. On April 26, 2011, it was announced that Olbermann's new show would debut on June 20 and would be named Countdown with Keith Olbermann. Olbermann was also heavily involved in the development of the rest of the network's news programming. The deal also included an equity stake in Current TV.
During the interim between shows, Olbermann launched an "official not-for-profit" blog called FOKNewsChannel.com, "FOK" being an abbreviation for "Friends of Keith". The blog featured political commentaries by Olbermann—including viral video versions of Countdown's "Special Comment" and "Worst Person" segments, as well as photographs of his outings at professional baseball games. On May 29, 2011, the FOKNewsChannel.com domain redirected to the Current website promoting the June 20 launch.
Olbermann was fired from Current TV on March 30, 2012. In a statement from Current TV, they stated that "Current was [...] founded on the values of respect, openness, collegiality, and loyalty to our viewers. Unfortunately these values are no longer reflected in our relationship with Keith Olbermann and we have ended it." Olbermann released his own statement, apologizing for "the failure of Current TV" and "that the claims against me implied in Current's statement are untrue and will be proved so in the legal actions I will be filing against them presently."
The two parties sued each other over Olbermann's firing. On March 12, 2013, it was announced that Olbermann settled his $50 million legal claim. In a joint statement, Olbermann and Current TV said: "The parties are pleased to announce that a settlement has occurred, and that the terms are confidential. Nothing more will be disclosed regarding the settlement."
According to Politico, Olbermann's professional reputation suffered greatly as a result of his dispute with Current, which accused Olbermann of making "material breaches of his contract, including the failure to show up at work, sabotaging the network and attacking Current and its executives." Purportedly, despite actively shopping other networks for offers, Olbermann was unable to find an outlet interested in hiring him. According to Politico, the fact Olbermann had been rendered unemployable as a result of the dispute, factored heavily during settlement negotiations between his attorneys and representatives from CurrentTV.
On August 1, 2022, Olbermann began producing and hosting a weekday podcast titled "Countdown with Keith Olbermann", for iHeart Media. It usually consists of a similar five block show from the TV days with three blocks changed out. The main, a dog in need, a headlines section, worst person, a sports rundown and the number one story either being a story of Olbermann's (usually his experience in the news media) or a short story from James Thurber on Fridays.
Olbermann has made several acting appearances either as himself or simply as a sports/newscaster, most notably as Tom Jumbo-Grumbo (a blue whale newscaster on the MSNBSea network) in several episodes of BoJack Horseman.
In October 2020, Olbermann called for supporters and what he described as "enablers" of Donald Trump, including United States Supreme Court nominee Amy Coney Barrett and conservative political commentator Sean Hannity, to be "prosecuted" and "removed from our society". Additionally. Olbermann labeled Trump "a terrorist" and called his supporters "a blight that will be with us for generations", further saying that Trump's "only barely-human delight comes from the morons in the crowd."
Olbermann is a dedicated baseball fan and historian of the sport, with membership in the Society for American Baseball Research. In 1973, when he was 14 years old, The Card Memorabilia Associates (TCMA) published his book The Major League Coaches: 1921–1973. The September issue of Beckett Sports Collectibles Vintage included a T206 card that depicted Olbermann in a 1905-era New York Giants uniform. He argues that New York Giants baseball player Fred Merkle has been unduly criticized for his infamous baserunning mistake.[dead link] He contributed the foreword to More Than Merkle, a book requesting amnesty for "Merkle's Boner". Olbermann was also one of the founders of the first experts' fantasy baseball league, the USA Today Baseball Weekly League of Alternative Baseball Reality, and he gave the league its nickname "LABR". Olbermann wrote the foreword to the 2009 Baseball Prospectus Annual. In March 2009, Olbermann began a baseball-related blog entitled Baseball Nerd. He has also written a series of articles on baseball cards for the Sports Collectors Digest.
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"Keith Olbermann". IMDb.com. Archived from the original on March 22, 2009. Retrieved October 30, 2008. https://www.imdb.com/name/nm0646021/
"Trump is Finished". YouTube. November 27, 2017. Retrieved November 28, 2017. https://www.youtube.com/watch?v=xmkXR7EL_RY&t=8s
"Keith Olbermann to Host New Podcast on iHeartMedia". The Hollywood Reporter. July 25, 2022. Archived from the original on September 7, 2022. Retrieved September 7, 2022. https://www.hollywoodreporter.com/business/digital/keith-olbermann-to-host-new-podcast-on-iheartmedia-1235185676/