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In May and July 1999, Olbermann also guest-starred ten times on Hollywood Squares.

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 became frustrated as his show was consumed by the Monica Lewinsky scandal.

In 1998, he stated that his work at MSNBC would "make me ashamed, make me depressed, make me cry." Olbermann left MSNBC for Fox Sports Net shortly thereafter.

At one point in the show he referred to Bristol, Connecticut (ESPN's headquarters), as a "Godforsaken place".

this began a long and drawn-out feud between Olbermann and ESPN.

TBS later hired Dirk Hayhurst, Pedro Martínez, and Mark De Rosa to provide analysis.

Tom Verducci also joined the studio crew, as he was replaced by Rachel Nichols as a field reporter.

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.Between 19 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." In 2004 Olbermann was not included in ESPN's guest lineup for its 25th anniversary Sports Center "Reunion Week", which saw Craig Kilborn and Charley Steiner return to the Sports Center 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.Olbermann left the show prior to the start of the 2010 season.Shortly before rejoining ESPN, Olbermann signed a contract with TBS to host the studio show portions of its coverage of the Division Series and National League Championship Series.

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