This is something to be worried about with Ainge. Rarely does he ever make a trade and you think, 'wow, he really got screwed on that one.' It is almost always the opposite. Inexperienced gms (like Jordan) may just be afraid to trade with Ainge thinking they are going make a terrible blunder.
Winslow was clearly the choice at #9, but pretend we had the 9th pick and we were ready to take Kaminsky, would anybody here be all that upset that we trade the pick for four firsts and decent 2nd rounders? We would be hailing Ainge once again. Jordan obviously overthought this one.