Story of the character
Jack Hess who has a master's degree in education and who taught six years at boarding schools on the East Coast, is the new Dean of Discipline at Harbor High. He is responsible for the measures to be taken after the gunshot incident, even though no criminal charges were filed.
He wishes to punish Marissa Cooper who shot Trey Atwood in the back to save Ryan's life, but is only able to expel her. When Ryan Atwood punches him in the face at the kickoff carnival after he brought Marissa as his date, Jack uses that to have expelled Ryan as well.
He gives Seth two months detention when he and Summer steal a tiki hut, which was a prop in Taylor's play, so Ryan and Marissa can have sex in the hut on the beach. He is also responsible for Summer losing the social chair to Taylor by tricking her to admit that she helped Seth steal the theatrical set.
At the end of summer dance, Summer sees Taylor and Jack sharing an intimate tryst and Sandy uses the information to blackmail Jack into leaving Harbor to save his career and get Ryan back into Harbor.