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Principal Herbert Hickey is a recurring character in Pepper Ann and the principal of Hazelnut Middle School.

If it wasn't for the first amendment to the United States Constitution, Principal Hickey would have outlawed freedom of speech in Hazelnut Middle School years ago. Unfortunately for him, the first amendment stands, and he has to put up with whatever odd statements the students dish out.

Principal Hickey doesn't seem to have anything against Pepper Ann personally, only against what he calls her "crazy misadventures". He can't see into her mind or predict when they're going to happen, but he gets away from them as much as possible. Once, he even sent her as an alternate on the Quiz Bowl team so that, for one week, he wouldn't have to "deal with any of her crazy misadventures". When her yearbook picture cost him the "School Yearbook Award", Principal Hickey could only say one thing. After muttering to himself the number of days until Pepper Ann graduates, he finished his statement with, "I think I'm going to be sick." Watch out, Hickey; Pepper Ann's here to stay!

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