A very pregnant Devon hosts a fundraiser with Jack as the object of the bachelor auction. Her college classmates attend; however, one by one, they fall victim to a murderer. Jack, Zymak and Deacon all work the angles of this case, with the evidence pointing firmly at Jack's new girlfriend.
Our man Billy Po is featured in this episode of racial tensions that are spawned in Little Italy. Billy is attacked after a date with his girlfriend, which leads Jack into an investigation of the death of a young Chinese immigrant.
The sudden death of Jack's surrogate father leads Jack and Deacon to investigate the policies of the nursing home in which he was residing. It turns out that once people move in, their stay is usually quite short.
Jack is offered a new job, which he considers as Devon prepares to sell KJCM and move to Tahiti with the father of her child. We are introduced to Nikki Malloy in this episode and the prospective new owners of KJCM. Jack and Devon deal with their imminent separation by arguing with each other every chance they can get.
Devon struggles with the sale of KJCM, wanting to ensure that her employees are well taken care of. She and Jack continue to lock horns, until push comes to shove in the delivery room! Jack has to decide whether to stay on at KJCM or move on to greener pastures.
Nikki shows who's the new boss by insisting Jack cover a prison riot near San Francisco. Jack arrives at the prison and becomes part of a chosen delegation to go inside and witness the atrocities the convicts are rebelling against. Unknowingly, Jack becomes the target of one of the inmates, who has a personal score to settle.
The convicts demand Jack broadcast their side of the story via KJCM, Deacon gets an interview with the prisoner on the outside, and Jack meets up with the prisoner with a bone to pick.
Jack tries to help out his radio hero from his youth by trying to convince Nikki to give him a job. Jack seems blind to the man's obvious faults and self-destructive actions.
A child of the Vietnam war, whose father was a U.S. serviceman, instigates a hostage situation into which Jack is drawn.
Jack tells Nikki about a situation he and Devon were trapped in a year ago, in which a vengeful ex-con and his gang kidnapped Devon in order to lure Jack to a payback situation.
Jack recognizes a woman who has been missing for years and in his pursuit of her he uncovers that she intentionally disappeared to avoid beatings from cop husband.
When Zymak's relationship with an immigration officer seems to be clouding his judgment in a murder investigation, Jack becomes involved at the request of one of the deceased person's relatives.
A former snitch seeks Jack's help in collecting his lotto winnings. He's in the witness protection program, and he's not a very popular citizen in San Francisco! When Jack isn't successful, the would-be millionaire approaches various familiar faces to attempt to retrieve the prize.
Jack and Nikki's tenuous friendship is tested when he questions her involvement with an ex-boyfriend, who has a substance abuse problem.
Jack struggles with his opinion of deadbeat dads and with giving his "Little Brother" a positive start with his father who is making an effort to reform himself.
A frequent caller to the show witnesses a murder; however no one believes her because the crime scene is cleaned up before the cops get there. She turns to Jack for help, protection, and comfort.
Jack's troubled young sister shows up on his doorstep. She and Deacon become emotionally involved and Jack struggles with the relationship.
KJCM's security guard is charged with murdering his son. Jack gets involved because the guard is suing KJCM for the advice he claims he received from Jack in how to deal with the drug problem in his family.
Jack and Nikki find themselves as proxies in a poker game; Jack's father's life is at stake.
The Castlemans are pressuring KJCM to take a stand in the upcoming election, Jack is greeted by his supposed daughter, and his high school friend is murdered.
Jack pursues the death of his friend, who had been homeless for many years. In his search for answers to Sonny's death he goes undercover on the streets and meets up with the hierarchy of the street dwellers. Jack's pursuits may cost him his job, as a young upstart in the Castleman dynasty covers his show without a problem.
Closing in on the answers to Sonny's death leads to connections to the candidates and the issue of the homeless, which in turn causes Jack to become the target of an assassin.