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.

As the Donnellys learn Sean's condition, Jimmy stews in a holding cell. Tommy finds comfort in Jenny Reilly. Nicky Cottero seizes control of the Italian mob.

After losing his health coverage, Sean is transferred to the psych ward. Jimmy convinces Kevin to bail him out. Tommy deals with guilt over taking the lives of Sal and Huey.

Hoping to collect the Donnellys' debt, Nicky threatens their mom, Helen. Sean comes home; Jimmy and Joey collect Louie Downtown's payments; Tommy takes a bribe.

Tommy gets pulled into Jimmy and Kevin's bookmaking action when he realizes the guy about to get busted for not paying is his friend Maxwell.

As Jimmy protects Sean, Tommy joins forces with Kevin to collect vig. Jenny struggles to maintain the family's diner and watch over her ailing father.

Emerging as head of the 'hood, Tommy gets scammed while trying to evict drug dealers. Jimmy demands payment from Jenny; Nicky learns the Donnellys are behind Louie Downtown's disappearance.

Kate helps Tommy get a job at an art studio. Nicky proposes a partnership with the Donnellys, but he'll only deal with Tommy, which infuriates Jimmy.

Dokey tests his partnership with the Donnellys by asking them to clear out a building of junkies. Forced to come to Kevin's rescue, Tommy inadvertently commits murder.

Reilly asks for help after he's ordered to vacate his building, prompting Tommy to uncover hidden family history. Meanwhile, Jimmy and Joanie struggle to situate Whitey's body.

Tommy makes a deal with Nicky for the identity of his father's killer. When Dokey humiliates Jimmy, Tommy and Kevin retaliate. Jenny finds closure concerning her missing husband.

Tommy and Jimmy have two different ideas on how to save the Donnellys. Tommy hatches a plan to get the family, along with Jenny and Joanie, out of town.