Ray goes to New York to arrange an illicit surgery that will hopefully save Smitty, as Season 5 ends. Sam agrees to help, but only if Ray commits a brutal act. Meanwhile, Daryll struggles with his loyalties as Mickey tries to get himself out of jail by turning the tables on Ray.
Ray searches for Frank Barnes in an attempt to get Bridget out of jail. In New York, Terry deals with the return of Damon's father and takes care of Smitty at Bridget's request. Back in Los Angeles, Teresa makes a confession to Bunchy.
Ray and Terry put their differences aside to try to fix Bunchy's problem. Jay asks for a secret meeting with Daryll to decide the future of the movie and their relationship. Bridget's last effort to save Smitty puts her in an unexpected place. In the wake of a tragedy, Ray turns on Sam.
Natalie's fame puts Ray's career in jeopardy when he becomes the story for the very first time. Mickey and Daryll celebrate getting the greenlight on their movie. Terry prepares to leave the Fite Club behind for good. Bunchy gets in over his head. Bridget takes Smitty's problem into her own hands. Ray hunts down the source of Sam's problems.
Ray is forced to step in and save Mickey from himself; Terry returns to L.A. with a devastating confession; Daryll and Mickey butt heads over the direction of their movie; Bunchy helps out a fellow inmate, on the condition that he'll help retrieve the settlement money; one Donovan goes to extreme measures to protect the family.
Mickey's screenwriting dreams stall out until he's pulled into a gruesome fix for Daryll's movie star client; Abby starts construction on the new bar while Ray searches for a solution to their problem; Terry tries to win back Maureen one last time; Bunchy's quest for financial independence gets derailed; Bridget tells her boyfriend who her father really is.
Ray cleans up the mess left after Natalie shot her husband. At home, Ray struggles to reconnect to his family and complete anger management. Meanwhile, Terry visits Conor at military school; and Frank Barnes visits Mickey and it threatens to sink him back into a life of violence.
A flashback to Ray and Abby's 21st anniversary when they went to Las Vegas to see Damon's first televised fight. In the present, movie star Natalie James hires Ray to protect her from her abusive husband, which draws him deeper into Sam Winslow's web. Meanwhile, hopes for a beautiful day are dashed at Terry and Maureen's wedding when tensions flare between the Donovans and the Dohertys.
Season 5 begins with Ray beginning court-ordered anger management after a family tragedy sparks a bar fight. Meanwhile, Mickey, Bunchy and Daryll prepare for Terry and Maureen's wedding; Bridget looks up a mysterious acquaintance in New York; Conor grows accustomed to military school; and Sam Winslow, a powerful new employer, comes into Ray's life.