>>56117845I think he was the champion before Kieran, and his laidback and lazy attitude doesn't bode well with Kieran's arrogance and harsh leadership style.
So he gets close to the player knowing A: It will piss Kieran off & B: The player will be a more easygoing leader than Kieran if he beats him.
Drayton also mentions he liked Kieran better when his hair was down, implying he was close with Kieran or at least knew him by association with Carmine, so he probably want's his old little buddy back.