Winning would both help and hurt the franchise... the Trib would get most of the $$ for all the World Series Championship merchandise. Certainly there would be a bump in everything short-term with all the bandwagoners hopping aboard, and there's no reason you couldn't make even more money in the short-term. What would hurt the value is the new owner wouldn't get the fame of being the owner when the Cubs win it all (statue in Chicago, etc). I think that's worth quite a bit of money. You also couldn't keep revenue at what it is after a win if you fielded a poor team, so that means less revenue for those who want the Cubs just to make tons of money off the fans' loyalty.