When Katherine discovers that a bully is extorting lunch money from Webster and his classmates, she enlists the crime-prevention dog McGruff to talk to the class.
George is so obsessed with Webster winning a derby that he builds the car without him, hurting his feelings since Webster wanted to build the car together.
Web's school, Franklin Cooper Elementary, is about to be renamed for his late father, until Cooper's nephew (Ron Reagan) steps forward to preserve the name of his uncle.
With the holidays approaching, George is elated after being chosen to play Santa in the Chicago Downtown Christmas Parade. However, when the parade is able to land a much bigger celebrity, Webster and Karen must break the news to George.
Webster feels guilty that his success as a dog-walker comes at the expense of his predecessor; and the expense of home repairs spurs Katherine (Susan Clark) to try to fix things herself.
The seniors dance Katherine (Susan Clark) promised to attend is on the same night as the Four Tops concert George bought tickets for as an anniversary gift. The Four Tops play themselves.
Katherine is in charge of an auction. One of the items is signed by a celebrity. Katherine thinks it was accidently donated, but Webster knows the truth. Guest star: Mike Tyson.
Katherine takes over the role of scout leader for Webster's scout troop. Another male leader doesn't like the idea of a woman scout leader. When an injury calls for quick thinking, Katherine comes to the rescue.
Webster gets an A++ for his essay about his parents. He then feels guilty that he wrote about his adoptive parents instead of his deceased birth parents.
Webster tries to buy friendship to fit in with the two coolest kids in his school, Joey and David. George finds out he's supposed to speak at a ceremony for Gloria Steinem.
