This Goldbergs-inspired special event picks up where the Goldberg family leaves off at William Penn Academy in the 1990s as former teacher and now Head of School John Glascott leads a faculty of teachers with wildly different views on how to mentor students and recruits his tough-as-nails-sister Lucy to join his staff and enroll her teenage daughters Felicia and Gigi as new students. Lucy is desperate to ensure they avoid the social pitfalls of high school and finds herself torn between Glascott's nurturing and communicative approach to parenting and Coach Mellor's tough-guy belief that physical competition brings out the best in students. Even Beverly Goldberg comes to visit the school's staff despite all her kids having already graduated and can't help but meddle one last time.

Adam loves director Steven Spielberg so much and decides to film an original script he wrote about Indiana Jones and his passion for directing is called into question. Meanwhile, Murray and Barry make a bet about whether or not a cheesesteak sandwich in New Jersey is the best one ever.