Dylan's estranged mother, Iris, returns to Los Angles which resurrects old family hostilities for she doesn't trust Jack with handling Dylan's trust fund, as does Jim. Brandon continues gambling and splurges his winnings on skis and a new car stereo. Meanwhile, David and Steve meet with the eccentric Icon Records Company president Curtis Bray, who tells David that he will give him a recording deal only if he fires his personal manager Steve. Brenda spends the entire weekend in her bedroom moping about her lost relationship with Dylan, while dreaming evil dreams on doing physical harm to Kelly whom she unfairly blames for her and Dylan's breakup. Also, Andrea goes to a luncheon for Yale acceptances where meets her old friend Jordan Bonner.

After Jack is killed in a mob-related car-bombing, Dylan struggles with his inner self urging him back to old drinking habits before he learns the shocking truth about his father's parole and true colors from Christine who revealed to be FBI agent. Meanwhile, Kelly continues to be obsessed with losing weight and begins starving herself, while she becomes uncomfortable when Jim asks Dylan to stay at the Walsh house for a while to avoid reporters following his every move. Steve turns down giving any more recording advice to David who struggles with meeting with Curtis Bray and Serge Menkin for a recording session on the day of Jack McKay's funeral. Also, Brandon's losing streak continues as his betting continues.

Gambling addict Brandon multiplies his addition by hiring a school bookie, Jeff, in order to pay off $1,500 of losses to Duke who's now out to get Brandon. Meanwhile, David finally realizes the true nature of the music industry when Serge continues to ignore his hip-hop material and forces him to record a repetitive, syrupy ballad. David goes along with it, but Curtis Bray does not like the new tune and outright terminates David's recording contract. Finally seeing the egotistical, two-faced shark that Curtis Bray really is, and the self-serving hack Serge is, David leaves Icon Records and goes back to apologize to Steve for the way he treated him. Kelly's eating disorder worsens when she starts taking diet pills. Also, Andrea tries to ease Dylan's depression over his father's murder by asking him if she can do an editorial on him.