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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.
As a teenager he often wrote about baseball card-collecting and appeared in many sports card-collecting periodicals of the mid 1970s.
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 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.He was a sports correspondent for CNN and for local TV and radio stations in the 1980s, winning the Best Sportscaster award from the California Associated Press three times. From 1998 to 2001 he was a producer and anchor for Fox Sports Net and a host for Fox Sports' coverage of Major League Baseball.From March 2003 to January 2011 Olbermann hosted the weeknight political commentary program Countdown with Keith Olbermann on MSNBC.