Ray's life is thrown into absolute turmoil when his father Mickey unexpectedly gets out of prison five years early, kills a priest, and arrives in LA, vowing to take revenge on Ray for framing him. Meanwhile, Ray's mentor, Ezra Goldman, and his law partner, Lee Drexler, need Ray to find a way to get a married action star out of a scandal with a transgender woman. Ray must also protect a beautiful singer from a stalker, but the case leads to tension between him and his wife, Abby.
Ray activates a plan to send his father Mickey back to prison. Meanwhile, Abby defies Ray and spends the day with Mickey and her kids. Ray handles two crises involving movie star clients: A-list actor Sean Walker receives a threatening message at home, and action hero Tommy Wheeler is blackmailed with a sex video.
Mickey spends time with Bunchy and Terry, insinuating himself back into their lives. Ray "buys" a talented hip-hop artist for his rapper neighbor. Ray's mentor, Ezra Goldman, holds a fundraiser in honor of his late wife, but he's haunted by the sins of his past. Meanwhile, Mickey is approached by an FBI agent with a Hollywood obsession.
Ray, Abby, and the kids visit Bel Air Academy, hoping Bridget will get into the prestigious school, but the day is interrupted when Ray has to take care of a case at a Beverly Hills hotel. Mickey, Bunchy and Daryll drive out to Palm Springs to visit Mickey's ex-girlfriend, Claudette. Terry starts a romance with his nurse, Frances. Ray finds out that the murder investigation against Mickey has been shut down.
Ray forbids Bridget from seeing Marvin but she visits him anyway and has a frightening encounter. Meanwhile, Ray flies to Boston to search for Sully. Abby and Deb commiserate over drinks and get themselves into trouble. Frank tries to shut down Van Miller's investigation. Mickey manipulates Sean into working with him on a movie project.
Ray, Terry, and Bunchy toast the anniversary of their sister Bridget's death. Frances shows up with a black eye, and Terry goes after her husband. Ray and Avi use force to get Bunchy's house money back. Mickey meets a former starlet at a spa. Meanwhile, Lena and Avi go after Van's investigations, and Lena has an altercation with her girlfriend.
Avi drives Sully from Boston to Los Angeles to meet with Ray. Conor wants to go to an awards show with Tommy Wheeler, but Ray has to get Tommy out of a situation that threatens his career first. Lena digs up Frank's secrets to get him to cooperate. Mickey works with the FBI to get incriminating evidence against Sean Walker.
Bunchy has a violent encounter with someone from his past. Ray is called to the Donovan Fite Club to handle a situation that has escalated in to a crisis. Ray meets with Ezra who pressures him about Sully, Mickey and the FBI. The police question Mickey about a recent murder. Ray sends Avi to protect Abby and the kids from Sully.
Just as Ray's life begins to return to normal, the FBI demands that he bring Mickey back from Mexico, where he is setting up a fight for Daryll. Abby, concerned that he won't face his abuse, forces Ray into therapy with her. Meanwhile Bunchy gets nervous about a job interview, Terry obsesses over his ex-girlfriend and Conor lands in hot water after assaulting a classmate.
Ray forces Mickey to return to LA and brings him to Ed Cochran, who holds a press conference taking full credit for finding and killing Sully Sullivan. However, Kate McPherson, a Boston reporter, doesn't believe the story and begins to investigate his death. In a desperate bid to control his father Ray corrupts a parole officer and has him take over Mickey's case.
Ray and Abby are eager to get Bridget into her dream school, but Ray's fractured relationship with movie producer Stu Feldman stands in their way. Mickey has a date with his old flame, Claudette - but first he has to find a way around Mr. Keith, his new parole officer. Kate McPherson heads to the Fite Club to try and get information out of Terry.
With her investigation in full swing, Kate zeroes in on Mickey. Meanwhile, the appearance of Tiny, a former member of Sully's gang, jeopardizes Ed Cochran's career. Plus, Mr. Keith sends Mickey to work at a Mexican restaurant, Abby meets a new friend at the gun range and Bunchy encounters a potential love interest at the bike shop where he has gotten a job.
Ray gets compromising information on Cochran. Avi follows Kate as she investigates, but Ray will need to give her a new story. Meanwhile, Abby tries to have fun with her prospective new neighbors, and gets closer to Jim, her cop friend. Marvin takes Bridget to a party at the house of ex-con/hip-hop mogul Cookie Brown. And Conor apologizes to Alex - but it doesn't go well.
Ashley asks Ray to go to bat for her friend Steve Knight, a self-help guru who beat up a waiter. Avi and Lena help Ray make contact with Volcheck to seek his aid in taking down Cochran. Mickey gets a stipend from Ray, but hopes for a bigger payday when he meets with movie exec Debra Gerson. And Bridget argues with Ray and Abby about a gift from Marvin.
It's Conor's birthday - and both Abby and Ray forgot. When Conor demands a party with Terry, Bunchy and Mickey in attendance, tensions run high as the whole family gathers at the Donovan house. Meanwhile, Ashley's stalker is back, and Ray comes face-to-face with Cookie Brown when the ex-con/hip-hop mogul shows up to take Bridget for a night out.
Lee Drexler returns from his honeymoon, only to be confronted by Cookie Brown, who demands the rights to Marvin's music. Ray arranges the deal, but then Lee reneges on it. Peggy Shaughnessy plants a seed of doubt in Kate's mind about the story that she published; Kate reopens her investigation but is threatened by a pair of Southie thugs on the street.
Ray tells Bridget how she needs to lie about where she was during the shooting, for her own safety - but Abby brings Jim over to tell her just the opposite. Lee and Ezra are convinced to give Cookie the rights to Marvin and Rekon's music, while Mickey starts to plan a pot store robbery with Shorty. Confronted with Patty's son, Bunchy struggles with his fears. And Kate visits a Walpole inmate to find out what went wrong with her article.
Ashley's stalker is back and making trouble again for Steve Knight - but when Ray intercedes, he learns that Steve is actually the dangerous one. Cochran gets a call from the President, nominating him for the FBI directorship - and vows to take the necessary steps to protect himself from the vetting process. Kate confronts Ray over the truth about his past, Abby tries to overcome her anxiety for Bridget's safety, and Mickey starts gathering the team for his robbery.
Ray starts to make arrangements in case he gets arrested when Kate publishes her story. Meanwhile, Cookie gives Ray a million dollars to track down a stalkerazzi video of the shooting. Mickey's robbery doesn't quite go as planned when Terry gets left behind - and arrested. Plus, Shorty's oxygen tanks explode while Conor is waiting in the SRO, leading to a confrontation between Ray and Mickey. And Ezra tells Ray and Avi that Kate needs to be stopped.
Ray is in recovery mode in the aftermath of the shootout, striving to reconnect with his family and repair his relationship with Bridget. Meanwhile, Bunchy and Teresa face impending parenthood together as Abby receives a medical diagnosis that threatens to upend the Donovan family. Hiding out in Nevada, Mickey plots a heist as Detective Muncie closes in on his trail.
Ray helps Hector handle a person from his past who risks unearthing a secret that could ruin his career. As Bunchy attempts to please a very pregnant Teresa, Abby offers him a lesson in marital compromise. Meanwhile, an act of petty larceny leads to a renewed sense of purpose for Terry - and Detective Muncie uses evidence against the Donovans to force Ray's hand.
An intruder breaks into the Donovan household, forcing the family closer together as Bridget struggles to maintain her independence. In Primm, Mickey schemes to rob a casino with the help of a lounge singer and a man named Ed. Meanwhile, with a baby due at any minute, Bunchy and Teresa navigate their marital woes under lockdown, and Ray visits Belikov in prison to strike a deal.
Looking for leverage to get the Russian mob off his back, Ray pays a visit to a Hollywood power-player and unearths a secret Ezra shared in the past. Lena and an ex-girlfriend take Abby for a night on the town to help her confront her fears over a recent health diagnosis. After returning from Primm to see his new grandchild, Mickey offers his boys a job prospect while trying to assimilate back into the family.
With the Russian mob threatening his family, Ray finds himself on a road trip with Mickey to Primm, in hopes of recovering money stolen from a local casino owner. Bunchy and Bridget take turns looking after baby Maria when Teresa withdraws to her family's house. And Terry gains confidence as a trainer.
Ray finds himself in a holding pattern, waiting to see if Belikov will be released from prison. An art dealer invites Ray to a breast cancer benefit where he encounters some former clients. Teresa spirals into postpartum depression. Meanwhile, Mickey goes to great lengths to convince the DA that he was the one behind the Minassian massacre.
Searching for a way to get Mickey out of prison, Ray turns to an old opponent to secure a bartering chip in the form of a less-than-wholesome family comedy star. A long-buried scandal leads Ray to an unexpected confrontation with a slick Hollywood agent and a former fixer of Ezra's. Meanwhile, without the protection of the Russians, Ray must help Mickey secure his own safety and gain admittance to the secure K6G prison wing.
After a public declaration from Marisol, Hector's rematch with Whittaker is cancelled. However, Ray enlists the help of Lena and Daryll to ensure the match proceeds. Meanwhile, an angry neighbor confronts the Donovans about Conor's reckless behavior. And Teresa's worsening depression causes her family to have her committed to a mental hospital.
When the head of the Russian mob arrives to find out what really happened to Belikov, Sonia and her daughter take refuge at the Donovan's, throwing her and Abby into close quarters. As both Avi and Lena question Ray's loyalty to Sonia, he must decide whether to help her or put the lives of his family and friends in jeopardy. Meanwhile, Mickey returns to Primm - in search of stolen money, Sylvie and vengeance.
Confronted with a crisis involving one of their own, Ray and his team strategize on how to use art from the Kovitzsky gallery as leverage. Meanwhile, after Hector's wife informs him that she and their daughter are moving to escape the incest scandal, he reaches a breaking point and enlists Ray's help in fixing the situation.
Ray's latest attempt to save Avi and square his debts to the mob takes a hit when FBI agent Frank Barnes nabs him before he can pull it off, so Ray must send Mickey to Las Vegas to place a hefty bet on the boxing bout between Hector and Whittaker. Later, in exchange for Federal protection, Barnes offers Ray a chance to turn informant against Dmitri.
Season Finale. Ray, hoping his deal with Hector will be his family's salvation, learns that Sonia has turned over incriminating evidence to FBI agent Frank Barnes. Ray is forced to wear a wire, but decides to play the Russian mob off the FBI, but things take a dangerous turn. Meanwhile, Mickey's attempt to cash in on the big fight leads him to a discovery that could help Ray against both sides.
Ray begins court-ordered anger management after a family tragedy sparks a bar fight. 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. Sam Winslow, a powerful new employer, comes into Ray's life.
Ray cleans up Natalie's mess, but at home he struggles to reconnect with his family and complete anger management. Unable to reach Maureen, Terry visits Conor at military school. A surprise visit from Frank Barnes threatens to sink Mickey back into a life of violence. Bunchy happens upon the business opportunity of a lifetime to provide for Teresa and Maria.
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; and Bridget tells her boyfriend who her father really is.
Ray's therapy is at odds with the high-stakes power struggle between Sam and her opponents. Mickey - at Frank's behest - seeks out an old friend of the Donovan's. Meanwhile, Terry takes Damon to New York to train for a fight; Bunchy is confronted by sins from the Donovan past; and Bridget tries to reconcile with Smitty - until a major crisis forces them together.
Abby makes a shocking decision that reverberates throughout the family. Ray runs interference for Natalie, while Sam shows him the lengths she'll go to protect her empire. In his attempt to free Bunchy, Mickey finds himself caught in the middle of someone else's war. Terry visits with Bridget and discovers a truth that shakes him to his core.
For Bunchy's sake, Ray is forced to step in and save Mickey from himself. Terry returns to LA 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. And one Donovan goes to extreme measures to protect the family.
Natalie's fame puts Ray's career in jeopardy when, for the first time ever, he becomes the story. 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; and Ray hunts down the source of Sam's problems.
Ray and Terry put their differences aside to try and fix Bunchy's problem once and for all. Meanwhile, Jay asks for a secret meeting with Daryll to decide the future of the movie and their relationship; Bridget's last-ditch effort to save Smitty lands her in an unexpected place; and in the wake of a tragedy, Ray turns on Sam - consequences be damned.
Ray being pulled from the East River by Police Officer Sean “Mac” McGrath. Taken over the bridge into Staten Island, Ray finds a chance at a new life, but the peace he comes to find is interrupted when Sam Winslow comes calling. With the ghosts of his past returning, and his father Mickey plotting something in prison, Ray may not have a choice but to return to his roots.
No matter how much he wants it to go away, Ray isn’t done cleaning up the fallout from his jump. People are asking questions, and there’s a witness willing to give answers that could rock Mac and Ray’s worlds. Across the country, Mickey’s heart attack behind bars forces the family to wrestle with what could be their father’s final days.
Ray is officially back working for Sam, and with Anita behind in the polls, they have to make a splash at the first mayoral debate. Darryl struggles with his leading man on the set of Mr. Lucky. Terry discovers a brutal new gym hidden in a warehouse in Brooklyn. And three generations of Donovans make their way from California to New York. Mickey’s coming, and no one knows what he has planned for his sons who betrayed him.
Mickey kidnaps movie star Jay White, and Ray has to get 3 million dollars from Sam Winslow to get Jay back in one piece. Mickey and Bunchy plot a future for themselves. Mac finds himself backed into a corner as Internal Affairs comes after him. Terry steps into the ring for the first time in twenty years. Smitty has to confront the secrets of his past and ends up calling on his future father-in-law for help.
Hoping to make up for lost time, Ray plans a day with Conor in New York before he ships out overseas with the Marines. Sam and Ray put together a fix to give Anita a bump in popularity. Sam tries to strike a deal with Mayor Ferrati. Mickey devises a radical plan to recoup his losses. Bunchy asks Terry for a favor.
A masked intruder with ties to the mayor makes a threat on Sam’s life. In looking for answers, Ray uncovers more than he bargained for. Now he’s got a target on his back and a friend whom he doesn’t know if he can trust. Searching for their ticket out of the country, Mickey and Bunchy board the Hampton Jitney. Bridget babysits her baby cousin, as Terry can’t stay away from his chance to fight again.
Ray brings Mickey to the FBI to turn himself in. Four months later, when one of the police officers’ heads turns up and Ray and his family are implicated in the murder, Ray finds his work with his therapist threatening to unravel. Mayor Feratti is back to his corrupt ways with increasingly unsavory jobs for Ray, including blackmailing a powerful family from the Donovans’ Boston past.
Ray must find a new way to get Detective Perry off his trail while reckoning with a personal loss. When Bunchy’s pharmacy is under attack, he takes matters into his own hands and is catapulted into the public spotlight. Daryll’s isolation mounts as he struggles to find his place in the Donovan family.
Ray gets closer with Molly Sullivan when he realizes their family connection. Claudette comes to New York and discovers that Daryll is on Detective Perry’s radar. Bunchy tries to leverage his heroism for a pay raise. Bridget gets closer with her music producer boss. Terry goes on a trip with his new spiritual guide.
Mayor Feratti ups the ante in his negotiations with the Sullivans, and Ray must step in to finish the deal. Bridget and Smitty are called in to fix Jonathan Walker Hanson’s unsavory publicity scandal. Claudette offers Daryll an opportunity to leave the Donovans once and for al. Bunchy grapples with the consequences of his drugstore violence. Terry struggles with the realities of his illness.
Mickey finally learns the truth about the botched heist, and he’s out to get his fair share of the money. Ray reflects on his early memories of Jim Sullivan while he and Molly track down Sandy and Mickey by any means necessary. Smitty is questioned by the police and confronted with the consequences of his actions.