Yeah, "winning" is rather broad. I remember thinking to myself when he gave that interview on ESPN Sweet 16 week and commented on Warren Buffet being in his late 80's being still able, etc. Jim stated all he has to do is "talk" and it's not as if he needed to physically exert himself. I remember thinking, hmm, maybe these players of his that he is just "talking" to when coaching, would actually like/prefer their head coach to be able to get in the mix, demonstrate, hands on, etc.
Additionally, when he stated he'll coach until "he can't win anymore" I thought to myself, that's interesting, because what has Syracuse "won" recently? When was the last time Syracuse won a regular season confference title or conference tournament title? Or, for that matter, even been close to "winning" one? What actually defines "winning?"
In any event, that was just my thinking when I heard the interview.