When Tommy attempts to divorce himself from the mob world and become a painter, Huey's widow (Molly Schaffer) helps him land a job at an art studio. Elsewhere, Nicky decides to partner up with the Donnellys---but he'll wheel and deal with Tommy only, enraging Jimmy.
Tommy, who seems to be emerging as the head of the neighborhood, helps a woman drive away drug dealers from her building, but he may get conned in the process. Meanwhile, Jimmy makes power moves to take over the area, demanding payment from Jenny and her father; and Nicky scrutinizes the disappearance of Louie Downtown.
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.
New Italian mob kingpin Nicky Cottero (Kirk Acevedo) shows his no-holds-barred style by threatening the Donnelly boys' mother (Kate Mulgrew). Meanwhile, Tommy is forced to accept Dokey's bribe; Sean continues his recovery; and Jenny deals with the consequences of bedding Samson (James Badge Dale). Dokey: Peter Greene.
Tommy is plagued with guilt when Kate (Molly Schaffer), widow of Irish-mob kingpin Huey, asks him to host her slain husband's wake. Meanwhile, Kevin and Joey go on a quest to find booze for the wake; Huey's brother (Peter Greene) begins to suspect that drug-addled Jimmy may be his sibling's killer.
As Sean's fate becomes clear to the Donnelly siblings, an antsy Jimmy stews in a holding cell. Meanwhile, an unsettled Tommy finds comfort in Jenny as their friendship begins to morph into something more serious; Nicky grasps control of the Italian mob.
Kevin's gambling debts pile up, prompting Jimmy to kidnap Kevin's mob-affiliated bookie, but one of the four Donnelly siblings may suffer the consequences of Jimmy's actions. Meanwhile, a responsible Tommy makes difficult family sacrifices.