There is a very fine line between boneheaded and aggressive. As you mentioned, three people can watch the exact same play and come up with 3 different conclusions.
I think the general tendency is to think that a play is boneheaded if it doesn't work, and aggressive if it does work. It's the same thing with managerial decisions. If it doesn't work, it was a stupid decision. If it works, it was a good decision. It's human nature to judge things in hindsight.
It would be great if we could all give our opinions before the play happened and the outcome is known, but obviously, that's not possible.