Gary is in danger after preventing a spa worker from being shot in the sauna. Turns out that the people who were going to kill him are mobsters and the spa worker is actually an FBI agent working on a case to bring the mobsters down.

Crumb is about to publish a manuscript about police corruption in Chicago, when he becomes the target of someone who doesn't want the book to come out. Gary and Crumb then narrowly escape a drive-by shooting, and Federal Agent Brigatti, who recently transferred to the Chicago detective squad, takes on the case and attempts to track down Crumb's potential killer.

As Brigatti carries out her plan to entice the thief with an expensive diamond pendant, her relationship with Gary grows more personal since they are forced to spend several days and nights together. When it appears that the case has been solved, Gary reads that the diamond will turn out to be a fake -- putting Brigatti's career in jeopardy. Armed with tomorrow's news, only Gary can save Brigatti's job by finding the true thief and returning the diamond to its owner.

When Frank Scanlon, a Chicago Sun Times columnist famous for his exposes, meets Gary during one of his daily saves, Gary piques the interest of the reporter, who believes that the rescues are more than coincidental. Intent on investigating Gary further, Scanlon demands that Sun Times cameraman Miguel Diaz hand over the confidential file he's been collecting on Gary. Meanwhile, when Gary reads in the paper that Scanlon is about to be murdered, he rushes to save him but the paper lists the wrong time of death - leading Gary to be found at the scene by police and subsequently arrested. Mounting circumstantial evidence even has Detective Toni Brigatti convinced of Gary's guilt. After escaping his arraignment, with Marissa's help, Gary becomes a fugitive desperate to find Scanlon's murderer.

When Gary's own investigation leads him to one of Scanlon's informants, he learns that at the time of Scanlon's death, the reporter was about to break a story on a murder-for-hire ring. With the help of Sun Times photographer Miguel Diaz, Gary obtains a printout of Scanlon's notes for his story that identifies six murders that were made to look like accidents. Meanwhile, Detective Brigatti uncovers some evidence of her own, which proves Gary's innocence and implicates someone with whom she works closely in the department. When Brigatti is subsequently taken hostage and about to be murdered, Gary must save her before the real killer sets him up a second time.

When Chuck returns to Chicago to get married, Gary recognizes Chuck's bride as Amber, a jewel thief. She is now calling herself Jade. Gary confides in Marissa who tells him that he must inform Chuck. Gary confronts Jade, who tells him that she truly loves Chuck and that she is really Jade. He decides not to tell Chuck what he knows. The next morning's paper says that a large diamond will be stolen from an auction. Gary and Marissa throw a private rehearsal dinner for Chuck and Jade to keep Jade there while the theft is suppossed to happen. Jade hires two female strippers to handcuff both Gary and Chuck. She then leaves and steals the diamond. When she returns to her apartment Gary confronts her. Jade tells Gary that she had to steal the diamond because it was once a national treasure of her country. Gary doesn't believe her story. He takes the diamond from her and puts it into the curator's mailbox with a letter warning them to tighten security.