They have the resources to be #1 easily, so the fact that there can be a debate between 1-3 is an indictment in itself. And there is light at the end of the tunnel for the White Sox. It is going to take awhile, but it isn't out of the question that within 10 years, the White Sox have a better ownership group than the Cubs.
Even if the Ricketts family eventually sells the team, the value and assets involved all but assures we are going to get another Ricketts-like entity or worse. The chances of getting a fully invested owner whose primary goal each season isn't maximizing revenue are slim to none.