George is upset that a younger pro football player has been signed to do the morning sports report. Webster suggests that he cover his hockey team's charity game as a human interest story. The station agrees, and George's report goes over so well that he starts to get more children's sports stories, which distresses him. Webster is upset when he overhears him saying so, but his spirits pick up when he and Rob audition for the job of covering kids' sports at the station.
Rob spends the night with Webster after he and his mother have dinner at his house. The next morning, his Dad comes to pick him up in his two-seat convertible. Webster doesn't see anything wrong until George and Katherine explain to him that Rob's parents are divorced and have been fighting over custody; they believe his father may have tried to kidnap him.
Ever since his sister was diagnosed with leukemia 10 years ago, Jerry has volunteered as a hospital clown for children with leukemia, and he invites the family to join him. George refuses to go because he saw too many dying children during his football career and can no longer handle it, but Katherine and Webster go with him. At the hospital, Webster befriends Mark, a boy from Wisconsin who is in remission from leukemia, and invites him to stay the night. At the house, he gets more activity and fun than his overprotective mother allows him to have.
Webster visits "Uncle" Jake Tyler, a collage classmate of George and Travis. Jake is a country music singer who, after his son died and his wife divorced him, has chosen a new career path: taking care of foster children. When one of their mothers comes back to pick him up, he has trouble letting go.
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.