Yahoo sports ranks the Bears owners as the 30th worst in the NFL. The Bengals & Raiders round out the list. The Lions are ranked 29th.
Here is the Bears excerpt:

30. Chicago Bears – Virginia McCaskey (Michael McCaskey, Ted Phillips): From a business perspective, no franchise in sports underachieves like this one. The Bears have a storied history, the NFL’s second-largest market all to themselves and, for the first time in forever, a saleable franchise quarterback in Jay Cutler(notes). The brand should be booming; sponsorship revenues should be raining down upon Halas Hall like M.J.’s fadeway jumpers in the mid-’90s. “They could take that thing and run it to the moon,” one owner says. “But they get less for what they’ve got than any team in our league.” The Bears also react cautiously to league-level proposals for increasing revenue. On a positive note, Michael McCaskey, as chair of the NFL’s Super Bowl committee, does a thorough and comprehensive job of reciting the rules before bids are considered. I can’t imagine where his peers would be without him.

http://sports.yahoo.com/nfl/news?slug=ms-ownerrankingspartone09020&prov=yhoo&type=lgns

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We don’t have a trillion-dollar debt because we haven’t taxed enough; we have a trillion-dollar debt because we spend too much. — Ronald Reagan