I'd vote for my old high school principal Mr. Malthrope for the "Biggest Criminal in State Service" award. They hauled him away in my junior year for stealing coffee from the teacher's lounge. LOTS of coffee. 3 cans a day worth of coffee. He was reselling the stuff at area flea markets.
For the "Worst Combover" award, I'd vote for the principal at my junior high, Mr. Evans. His pate looked like a high wind in a wheatfield.