For a 17-year-old (even a fairly-well-connected one) an Air is a pie in the sky request. If he had asked for a nugget of platinum or an Oscar, it would have been obvious that he was joking. As it was, he (probably) asked for something that to him WAS obviously joking, but to most of us is an easily-attainable object; that inequity easily leads to the current situation.
I'm not saying that's how it happened (also: I have no inside information or anything) but this is why I'm not prepared to burn the kid at the stake for it. A lack of experience led to a critical mistake; one that I don't think he'll make again. It sucks for him that his mistake is so public, but that's that's the way it goes.