When wealthy Tyler refuses to invite Orlando to his party and mocks Orlando's cheap sneakers, Nick must prevent a fight. He finds out that Orlando is sensitive about being from a poor family. But after promising to buy lunch for Orlando, Nick gets an urgent call for an audition and cancels the lunch. Since Orlando bragged about going to lunch with a teacher, the other kids now insult him for being abandoned. Orlando furiously stalks off. Later, the other kids inform Nick that Orlando barricaded himself in the school's boiler room. When Nick tries to get him out, he discovers that the room is full of electronic supplies and valuables that janitor Lloyd has been stealing for years. Lloyd appears and almost chokes Nick before a security guard takes him away. Nick tells the others that Orlando found the stolen materials and was able to run for help, thanks to his sneakers. Orlando becomes the school hero, and Nick realizes that teaching is rewarding.

Nick returns from summer vacation to discover that the middle school has become the Gerald R. Ford High School for troubled teenagers, and immediately locks horns with the new principal, brilliant Dr. Katherine Emerson. She is a college professor from the Midwest who has written a book about urban education but has yet to test her theories in real life -- and is unimpressed with Nick's unorthodox teaching style. Already at a loss over how to reach the older students, Nick suffers a bigger loss when Elana calls to end their relationship.