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 cuddle, Ray finds his work with his therapist threatening to unravel. Meanwhile, 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, and 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 all, while Bunchy grapples with the consequences of his drugstore violence, and Terry struggles with the realities of his illness.

After Feratti's display of force, Ray and Terry travel to Coney Island to track down Ray's missing car. Mickey, Daryll, and Sandy continue their quest for the truth about the 1977 heist. Bunchy uses a few tricks he learned at the pharmacy to make some quick cash, and Smitty seeks revenge on Adam Rain.

Things heat up between Molly and Ray, but their families get in the way when Bridget, Bunchy, and Jim Sullivan all need Ray to fix their problems. Terry and Smitty help Ray with some detective work and Ray struggles to stay on Mickey's trail, while at the same time keeping Detective Perry off of his own.

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.

Gary O'Malley seeks justice from the Sullivans, while Ray and Smitty must cover for their own actions. Daryll calls Jasmine with an opportunity that lands them face-to-face with Declan Sullivan. Terry and Bunchy head back upstate to settle some unfinished business with the Shaman.

With his back against the wall, Ray turns to Judge Scholl to clear his name with Detective Perry. Daryll is pushed to the edge by the Sullivan family. Mickey continues to chase Jim's money. Smitty tries to justify his betrayal to Bridget. Terry makes an unexpected friend at physical therapy.

Ray finally learns the truth about his sister Bridget's passing. Terry reckons with the passing of a friend and his own mortality. Mickey's quest for the money he's owed comes to a head with a deadly face-off between the Sullivans and the Donovans.