Yeah. Ultimately for the long-term future of the franchise, it's better that we won it under Theo/Jed than we would have been if we won a "lightning in a bottle" title under Hendry like the White Sox did, but there will always be a part of me that loves the 03 and 07/08 teams and wishes they would have won. That's actually kind of a rabbit hole I never thought of. How different the franchise would be today if the Cubs had won it in 03. Does the Tribune still sell the Cubs? If so, does the Ricketts family still buy them if they didn't have the historic drought anymore? Does the Trib Co authorize the spending spree that basically gave us 2 division titles in 07-08? Obviously its much less likely that Theo comes on board, etc etc etc You could make a fairly solid case that the Game 6 collapse was indirectly a net positive for the franchise. Because they got so close and lost an entire generation of Cub fans became thirsty for the elusive championship, attendance skyrocketed, increased fan interest and enthusiasm created the level of accountability that the Cubs didn't have to deal with as much in the past. (this is where it starts to become a stretch) There were a lot of other factors at play, but this increased demand probably played some small part in the value of the Cubs franchise increasing. Perhaps this value increase made it more attractive for the Trib to sell off when Zell and Co were going through bankruptcy, causing them to open the checkbook and bring a bunch of veterans in which led to 2 fun playoff seasons but no long term vision. Once that run ended the Cubs were baren of young talent leading to a situation where a large market team with a historic championship drought basically had to start from scratch. Enter Theo who was looking for a situation like the Cubs and the rest is history. You make it sound like losing game 6 caused attendance to go up. Attendance rises following playoff runs, because fans initially doubt the success as the year begins but the year after a run (99, 04, 08, 16) the excitement is there at the beginning and attendance goes up. There's no doubt in my mind that the Tribune still sells after WS victory. They were in a financial situation that demanded liquidation of non-core assets. The only question is if the new buyer would have held onto Hendry any longer and/or not gone after Theo & Co. I'd bet very heavily that a post 2003 WS appearing and maybe winning team would have been no better off by the time the team would have been sold, because of Hendry's terribly inefficient way of valuing hitting. They would have sold the team, the team would have been bad and the new owner would feel lots of pressure to make management changes. Losing game 6 didn't gain the Cubs anything.