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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.he later co-authored a book with Patrick called The Big Show about their experiences working at Sports Center; he also said that the short-lived ABC dramedy Sports Night was based on his time on Sports Center with Patrick, ABC having been co-owned with ESPN since 1985 (ESPN now produces all sports coverage on ABC, which is branded ESPN on ABC).
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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.
In the early-to-mid 1980s he was a sportscaster on the old WNEW 1130-AM radio station in New York City.
In 1984, he briefly worked as a sports anchor at WCVB-TV in Boston before heading to Los Angeles to work at KTLA and KCBS.
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.