With the World Series victories of the Boston Red Sox and Chicago White Sox earlier this decade, the Chicago Cubs now stand alone as baseball’s historic example of poor management, baseball ineptitude, and postseason futility. Sure, teams like the Pirates and Royals are more laughably inept now, but only the Cubs prove that such awfulness can last for centuries.
Cubs fans had hoped this was changing recently with the 2007 sale of the Tribune Company to angry munchkin Sam Zell. Unfortunately, anyone who has actually worked for Sam Zell could have told them not to get their hopes too high; predictably, the Cubs have underachieved under Zell’s brief ownership (of course, he’s been trying to sell them the entire time). And now, the sad-sack story of the Cubs has reached new heights/depths with the news that the team - one of the most valuable properties in all of sports - may be filing for bankruptcy.