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Season 2 ends with Mickey hatching a new plan that sends him to the races to bet big. Meanwhile, Abby becomes torn between her two potential protectors, Ray and Jim.
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 runs afoul of a corrupt FBI chief, gets too close to a nosy reporter from Boston who is trying to expose him, and becomes the hired fixer for a sadistic self-help guru; Mickey is forced to go on parole and schemes to make it big; Abby meets a man who is willing to do almost anything for her; Bridget's clandestine relationship with teen rap sensation Marvin Gaye Washington takes a surprising turn; Terry wants to sell the Fite Club; Bunchy struggles to find love.