When budget cuts threaten to gut Whitlock and put his job in jeopardy, Jack recruits Mary, Stef, and Michelle to take down the Superintendent. Durbin plans an appeal to the heart, while the students plan an appeal to the soul.

Jack accidentally loses a significant amount of money and it falls in the hands of the students. As Principal Durbin and Helen investigate who stole the money, the students and teachers admit to other wrongdoings.

As the school prepares for winter break, Jack tries to record a lecture on Thoreau's transcendentalism as a way into the University of Wisconsin's philosophy department. Frustrated and unable to finish the video, he falls asleep and has nightmares.