New Italian mob kingpin Nicky Cottero shows his no-holds-barred style by threatening the Donnelly boys' mother. Meanwhile, Tommy is forced to accept Dokey's bribe; Sean continues his recovery; and Jenny deals with the consequences of bedding Samson.
As Jimmy tries to protect Sean, Tommy joins forces with Kevin to collect payments. Meanwhile, Jenny supports her ailing father while trying to keep the family business afloat; and a look back at Kevin's childhood reveals the genesis of his gambling passion.
Joey tells Father Dufelt how Tommy caused Jimmy's horrible leg accident. Both have trouble trying to establish themselves as the neighborhood's criminal boss. Sean and Kevin bicker. Tommy is suckered into helping another 'innocent' female. Jimmy's extortion now extends to Jenny's father's bar.
Tommy finally pursues his dream: art, as the assistant to Kate's friend, painter Munst. He seems to treat Tommy as a gopher, proves a good teacher but demands priority commitment. Nicky finds out that Jimmy stole Louise's business, but decides to seek a more lucrative deal rather than bloody revenge. Councilman Jack Trevor demands Dokey restores order, or no building deals. Jimmy refuses to involve Tommy, but Sean tells him anyway, in time for an offer to replace Dokey. Dokey finds out about Whitey. Jenny reports her dad missing.
Tommy agrees to help Jenny's father keep their restaurant, which Dokey has managed to get declared 'unsanitary'. Joanie discovers that addict Jimmy stabbed Whitey to death, and helps him dispose of the body. Jimmy's creditor Jonesy, a corrupt ex building department employee, tells the boys to talk to their late father's friend Franny Kenny. However the the paper trail goes cold. Trish explains to Nikey about the Travis-Dokey-Alo real estate connection. Ma Donnely asks the boys to change their ways in order to avoid risking the same fate as their dad. Kevin has a Greek...
Joey is stabbed while in protective custody. Jimmy goes behind Tommy's back and tries to re-negotiate Tommy's deal with Dokey. Tommy and Kevin kidnap buildings inspector Anthony Lino who has been condemning the buildings on the block including the Diner. Elsewhere, Nicky tells Tommy that Dokey was involved in his father's death.
Since Tommy has no evidence that would put Dokey in prison, Frank advices Tommy to leave town with his brothers and mother. Sean refuses to leave because he wants to marry Nadine, but Tommy talks him out of it. Tommy asks Jenny to come with them, but she says she can't. Jimmy is planning to kill Dokey with Joey's help. They see Dokey's men, but no Dokey, so they follow them... Alo summons Nicky to tell him about Tommy, confident that he's one step ahead of Nicky.