After losing out on a chance to get out of Toledo and into his dream job at a prestigious university in Season 1, disgraced Harvard philosophy professor Jack Griffin remains determined to get out of town and regain prominence in the academic world. To do this, Jack decides to begin work on a book detailing a new philosophical thesis. This thesis will require him to immerse himself in Toledo more than ever before while continuing to enlist the help of his students and friends at Whitlock - including Principal Durbin. Jack will also find himself intellectually challenged and charmed by a woman he meets in the last place he'd expect: the payroll department of Whitlock High.