A mountain of debt at Wrigley

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The Setup

When Tom Ricketts purchased the Cubs at the end of the 2009 season, he spoke openly about how important it was for him to bring a championship to the north side of Chicago. (It's been a few years.) That's certainly possible, but previous moves by general manager Jim Hendry have handcuffed the team on a nearly unprecedented level. The contract situation Ricketts inherits is among the worst in baseball history, and with so many immovable players on the roster, rebuilding will not be an option in the near term. That, in effect, means if the Cubs are going to get to the World Series for the first time since 1945, it's going to have to be with this group.