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At his expulsion hearing, Van points out that he's only eighteen credits short of graduating from Coolidge, so proposes the alternate punishment - Instead of expulsion, he has to graduate from Coolidge. Mr McDougal points out that no matter what, they'll be rid of Wilder, so why not see what he's made of. Wilder then proceeds to get passing grades in all of his classes, despite not attending one all year & cramming everything he needed to know into a few weeks.
In Freshman Year, Van goes up to the militarian Dean Reardon, gives a "The Reason You Suck" Speech before challenging him to War Games, the loser leaving Coolidge; which leads to this exchange:
Dean Reardon: Prepare for a good old fashioned ass kicking, son.
Van Wilder: If I were your son, I'd kick my own ass.
Moral Event Horizon: The dean in Freshman Year crosses it when he tries to shoot Van and his dog near the end.