Bob was the reason Ricky had a rough childhood. He is also the reason that Ricky's birth mother, Nora, started doing drugs, leading her to go to prison (but she gets sober). In the episode The Father and Son, Bob gets out of jail but he is on parole. Bob was in jail for sexually abusing Ricky Underwood. However, he goes back to jail when Jack sees him violating his parole when he sees Bob buying drugs.