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.