I feel Tails would probably takes over a villain base later on. Whether it is the Battle Bird Armada or the Dark Legion I feel that he charge of one of them. I feel that when he defeats the Battle Lord he will take over as leader. As for the dark legion he gave them the eye that I am guessing that he is a chair person in the future.
The Dark Legion was in control of Lien-da and Shadow but I feel that he may some authority on them or an army that can be a threat like Robonik’s robot army or the Ixis mages.