Jimmy's plan to help his brother Kevin out of gambling debt with a truckload of stolen designer shirts backfires, forcing the two to kidnap local mob boss Sal Minnetta's nephew Louie. When Sal's right-hand-man Nicky Cottero decides to take the matters into his own hands, it's up to Tommy, the brainy one of the Donnelly brothers, to choose between fighting for his family and life as an honest man.

While Jimmy is sitting in a holding cell, Tommy and Kevin visit him without any remorse for what they did to avenge their brother and protect their family. After everything, Tommy decides that it's the time to confide his feelings for Jenny Reilly, which ultimately leads to more than friendship.To cover their back, the brothers dispose of the body. Meanwhile, Nicky Cottero seizes control of the Italian mob while the murder investigation begins.

When Sean loses his health coverage, the hospital moves him to the mental health unit.

Tommy is shocked that Kate asks him to host the murdered ringleader's wake at the Firecracker. But the brothers rapidly find out that they don't have enough alcohol to host the event. Kevin and Joey Ice-Cream must find lots of alcohol, and fast. Meanwhile, Jimmy puts himself and his brothers in a bad situation when, while under drugs, he appears to pay his respects to Huey's brother, Dokey.

Tommy realizes that the new mob-boss means business about collecting his debt when he threatens the boys' mother (Kate Mulgrew); Tommy steals a box that Dokey wants.

Tommy involves himself in Jimmy and Kevin's bookmaking scheme when he realizes the guy about to get busted is his friend Maxwell (John Lavelle); Jenny learns about her father's (Kevin Conway) medical condition when the diner receipts go missing.