I think Theo is doing it right from the business perspective.
Most teams would need to spend 80-100 mil to be close to .500 during a rebuild in order to draw fans. However, as long as the cubs keep the "experience" high, they will still draw close to 3 million fans.
The difference in those 250k fans is probably less than the difference of a gutted payroll, ESPECIALLY if they can move high priced players like Soriano.
While there is no such thing as a sure thing, we can't argue it both ways. The excuse for a pathetic White Sox farm system has always been "Because we always finish about .500, we do not get premium picks". Well okay, the Cubs are playing for Premium picks, fine.
But because of the size of their fan base and the location of their ball park, the Cubs are going to keep turning a good profit, be able to save up their resources and attack foriegn scouting while selecting top level prospects in the draft. When they are ready to spend, they will have some extra money saved up.
It would never work for the White Sox because they would only draw 5,000 people to the game. But the Cubs are the Cubs and they will be fine doing it this way.
If it will work, no one knows, but they won't be in a bad position because of it.
They also have a smart marketing department. They are lowing non-premium seats in the ball park and have consistently pushed the message of "we are new, be patient with us, we will build this up right". Loyal fans ARE going to buy into that.
I think its pretty telling the Cubs are marketing a complete tear down better than the White Sox are marketing are near division championship. I hope Brooks is ashamed of the job he did this year.