While serving as County Prosecutor, Masconi became partners with Cannavaro and would frequent his clubs to have sex with teenage girls. One of his and Cannavaro's clients was Judge Daniel Dolan, who would have sex with girls aged as young as twelve. In 2010, Masconi and Cannavaro trick Dolan into sleeping with an underage trafficked girl named Miyako Nara. Masconi then blackmailed Dolan into bribing local assemblymen and the Governor, under the guise of campaign contribution, to get his political cronies in power and ensure that Masconi remained in power. In 2012, Masconi set up a fake public relations firm under his mother-in-law's name to launder the kickbacks he got from a juvenile facility called Knollwood. To this end, Masconi had Dolan stop writing checks and instead send every juvenile delinquent that came into his courtroom to Knollwood so Masconi would get more kickbacks. Once convicted, the girls would be forcibly drugged and be physically and sexually abused, as well as neglected.
One night in 2014, Masconi went to one of Cannavaro's strip clubs, where Cannavaro let him hang out in the VIP room. Masconi got drunk and said he didn't like any of the dancers because they were slutty. He sent Clare Wilson, an underage waitress, to serve Masconi drinks. Masconi started groping Wilson while Cannavaro's bouncers turned a blind eye. Wilson told him to stop, but Masconi becomes enraged and rapes her. After raping Wilson, Masconi and Cannavaro leave her in an alley. When Wilson is sent to the hospital to have a rape kit done, she refused to speak with Sergeant Benson and Detective Rollins and went home. When Rollins and Detective Fin find her and bring her to the hospital for a drug overdose, she tells them that she was raped. When Masconi hears from Cannavaro that the SVU detectives are investigating her rape, he charges her with fraud and has her arrested so she couldn't testify against him. A.D.A. Rafael Barba meets with Masconi and tries to convince him to release Wilson so she could testify against Cannavaro, but Masconi refuses.
At trial, A.D.A. Gina Masconi, Bobby's wife, asks Dolan to deny bail, and Wilson is remanded to a juvenile facility. Afterwords, Masconi uses his connections to have her transferred to Knollwood to make it harder for the SVU detectives to get Wilson back in their jurisdiction. Eventually, the NYPD raid Cannavaro's strip club and arrest him, after which Assistant U.S. Attorney Connie Rubirosa has Wilson released from Knollwood. Later, Benson and Detective Amaro go to question Masconi about his ties to Knollwood, and he says that it is a good place to send juveniles. When they confront him about the abuse and neglect that happens at there, Masconi claims that they are being lied to by Wilson and that they believe everyone is a victim. After the detectives question Dolan, Masconi sends Dolan a picture of him with an underage prostitute to blackmail him into quitting, after which Dolan commits suicide. Eventually, Barba and Amaro get Cannavaro to admit that Masconi raped Wilson and that he was covering for him. Afterwards, he was arrested and is brought into the precinct, where he is shown nervous after realizing he was exposed. Wilson identifies him as her rapist and he is promptly charged.
At trial, Masconi was defended by an upset Gina. It can be presumed she couldn't avoid an acquittal for Bobby's crimes, and after the public scandal and smearing legal corruption, Gina likely resigned or was forced to retire, while presumably divorcing Bobby to avoid further shame.