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Home to the Tribune Co., Chicago’s iconic but embattled media owner, the third-largest market is now on the front line of today’s media woes. Under crushing debt of about $13 billion, Tribune, owner of the Chicago Tribune, WGN-TV, WGN-AM, WGN America superstation and CLTV, filed for bankruptcy late last year.

Real estate mogul turned Tribune chairman and CEO Sam Zell recently admitted on TV that buying Tribune was a “mistake,” and has tried just about everything to turn business around.

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