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Looking at those Forbes lists that come out and show who's making all the money, it is extremely, extremely rare that any major league baseball team is willing to lose money, whether they are chasing a pennant or not.  The only time I've seen a team come out in the red, even slightly, is the Detroit Tigers.  I think the Tiger fans should be happy for their ownership: they always seem willing to spend money to bring in talent, and are willing to take a loss in doing so.  But it's a very minor loss.
Local sportswriters like Steve Kelley talk all the time about how local owners need to step up and take a loss for the local sports fan.  I don't know what he's smoking, because it's a pipe dream.  Nobody ever does it.  Heck, our local owners would rather move to another city before taking a loss.