Adam is assigned a term paper on a great person in history, and he decides to make a movie about his grandfather but finds all of Pop’s war stories mundane. Pops takes matters into his own hands and decides to tell more exciting stories based on an old television series. Meanwhile, Erica returns home to confront Beverly for over-mothering her. Murray insists Beverly teach Erica and Barry basic life skills, but she worries Erica and Barry will be too independent.

Erica tells Beverly she is going to spend the first night of Hanukkah with Geoff and his family; Beverly worries and starts a competition for who hosts the best Hanukkah party; Barry seeks advice from Pops on how to be cool.

The Goldbergs-inspired special event picks up at William Penn Academy in the 1990s as 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.