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In 1984, Olbermann briefly worked as a sports anchor at WCVB-TV in Boston before heading to Los Angeles to work at KTLA and KCBS.

His work there earned him 11 Golden Mike Awards, and he was named best sportscaster by the California Associated Press three times.

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.

In 1998, Olbermann joined Fox Sports Net as anchor and executive producer for The Keith Olbermann Evening News, a sportscast similar to Sports Center that aired weekly on Sunday evenings.

Back in 2008 he and reporter for WNBC in New York, Katy Tur.