No, it is not wise at all. You are very unlikely to win a pissing contest with the school board unless you belong to some protected status group. However, Political Correctness, Zero Tolerance policies, and Bureaucratic Paranoia have created an environment where trivial, harmless and benign activities or statements can result in serious consequence.
That isn't the harm I was thinking of. I meant the harmful effect of teaching the kid that the rules don't apply to him, that the school has no authority, that he is untouchable and his parents will fight the school if they try.
Those parents are going to be called to the school a LOT. And the poor kid will make a lousy student, and a lousy employee.