I herby decree that all future small market title winners receive an asterix next to their rings.

There is a constant battle within each side.
Within the players' side, the mid-class want to earn their pay checks while the superstars want to dictate where they can play.
Owners side have to deal with small markets crying to large markets. Small markets want to handcuff large markets so the small markets can "compete".
Small markets are most likely going to get more of the profits from the large markets through revenue sharing, but they also want to hold the power to keep their players on a leash.
So if it were not for greed, when a small market team wins a title in the future, they won it because of a handicap.