Ordinarily, I wouldn't worry about Ainge wasting a draft choice on the airliner full of baggage that is Upshaw.
But Ainge loves him some tall stiffs - Robert Swift, Yi (Why?), Patrick O'Bryant, Fab Melo, etc.
But I do find some humor in the miscast notion above that money cures character flaws - when the facts are quite the opposite. Money exacerbates flawed character, because it serves as an enabler. The idea that Upshaw would respect the pro game because of his paycheck is categorically rejected here.
The answer to the OP - absolutely not at 16, and probably not at 28.
I personally hope we don't use either pick, sending them out for immediate help.