The generated wealth of these franchises is tied to the debt associated with purchasing them. While Rickets and Cohen have greater wealth then Reinsdorf, I think teh SOx and Bulls generated more wealth for JR then the other two at this point in time.
I am guessing on the Rickets Balance Sheet the cubs and surrounding projects in that area are a major drag. The investment into buying the team, rehabbing the stadium and surrounding area is not covered by the operations of the team and entertainment entities.
JR shouldn't have an issue in the world when it comes to his team's fiscal status and he's sitting $4B in invested assets with the Bulls and Sox free and clear of any debt.