I'm not bashing anyone but there must be some observations made obvious.

He's lived in Chicago, the Bulls comment makes sense. Appealing to his home town.

"NOT BAD" - do you REALLY think he knew to say that or do you think someone prompted him?

There are very smart people that control his speeches, people behind the curtains, to get the maximum appeal from the audience in which he is speaking to. Everything is scripted ever so carefully. Always keep this in mind. He's trying to win you over, for your vote.