It does not necessarily mean that. In this case, however, I think both happen to be true.
If not "small", at the very least, it's a shrinking fanbase. The incoming owner is going to have to figure out something to change the trajectory of this team's market share. Sure, winning absolutely MUST be part of that, but unless they can rattle off a bunch of pennants in quick succession, they'll still be struggling to make themselves relevant in a city were the Cubs are as dominant as ever.