A former San Francisco police detective suffering from an extreme case of obsessive-compulsive disorder is called in to investigate an apparent assassination attempt of a mayoral candidate in which one of his bodyguards is killed.

With an introduction to Monk's talent, his phobia's, and need for an assistant, Monk investigates the murder of the candidate bodyguard and a political worker. He determines the candidate was not the intended target.

When billionaire software magnate Sidney Teal is shot dead by ex-cop Archie Modine after allegedly turning mugger and another policeman mysteriously flees the scene, Stottlemeyer calls in Monk to investigate. Meanwhile, Sharona threatens to quit (this time for sure) when her paycheck bounces, and Stottlemeyer is hounded by reporters demanding information on "Fraidy Cop."