In this fourth book of Timmy Failure's memoirs, Timmy is forced to take his investigation into stolen charity funds on the road when his mother forces him to help her boyfriend move to Chicago. They are on the road in a cross-country trip that includes Timmy's mom, Total the polar bear, Doorman Dave, and criminal mastermind Molly Moskins. It's a world gone mad, where good becomes bad, and Timmy Failure is a condemned man.

Through a series of letters to his father, a private investigator, fifth-grader PJ "Clueless" McGee tells of his efforts to discover who stole macaroni and cheese from the school cafeteria.

While his mother and doorman Dave celebrate their wedding, Timmy visits Florida where he forges a new partnership with Dave's nephew, Emilio, when a surprise newcomer shows up and he encounters a thieving six-toed cat.