John Taylor Gatto won the New York State teacher of the year award in 1991 (New York state's education website). His ambition to be a great teacher led him to the realization that the system itself is broken and he was so disgusted with it that he resigned.

This pattern matches to the standard failure mode where exceptional individuals assume that others are more like them and therefore more competent than they actually are. This causes them to conclude that institutions are more flawed than they actually are.