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City contractor Tony Rosatti is killed in a professional hit. Briscoe and Green's main suspect is the victim's wife Sherri. He was planning to divorce her for cheating on him, so she wouldn't receive any money under the terms of their pre-nup. But now she has inherited a large estate including a $3m life insurance policy. A $50,000 payment from her account is traced to a hitman named Jamie Astangura. He is in jail and couldn't have killed Rosatti himself. Jamie says he doesn't subcontract murders, and someone else must be the killer.

Sherri's boyfriend Randy Porter is arrested after the detectives find a burner phone in his home that was used to contact Jamie. Randy says he doesn't know where the phone came from and thinks Sherri is framing him. He suggests her father, a retired police officer, knows how to hire a hitman. In turn Sherri says Randy could have forged her name on the transaction. With no evidence as to who actually killed Rosatti, [=McCoy=] charges Sherri and Randy for conspiring with Jamie Astangura.

But then [=McCoy=] finds that two payments of $50,000 were made to Rosatti by his friend "Bobby Vig" Vignerelli. Bobby Vig calls Rosatti's lawyer Austin Foster - saying that Rosatti left instructions to do this if Bobby Vig were threatened with prosecution. Foster produces an unopened parcel Rosatti sent before his death. It contains a videotape in which Rosatti says he wanted to die, so he hired a hitman to kill him and framed Sherri and Randy. A clause in Rosatti's will says that if he commits suicide, Bobby Vig inherits everything; Branch anticipates an unpleasant legal battle.

!!!This episode contains examples of:
* AffablyEvil: Jamie openly enjoys being a professional killer, and talks about it cheerfully as if he did any normal "job."
* AwfulWeddedLife: Both Rosatti's wives describe their marriages to him as this.
* FrameUp: Randy accuses Sherri of this, but it's the victim who was framing both of them.
* GoldDigger: Sherri is at least perceived as this, although she insists she's not and Rosatti was heavily in debt.
* GoOutWithASmile: Tony Rosatti metaphorically went out this way. He set up his own suicide, but as his video message insinuated, he had immense pleasure knowing that his wife would suffer greatly for it and that he went out peace of mind, something he wanted for years.
* ManipulativeBastard: Tony Rosatti managed to play everyone, including close friends, in his ploy for revenge against his cheating wife and her lover. When he revealed on his last video message about his plan, he knew that if it was being played, then the plan failed, but knew that whatever happened beforehand would be enough to ruin his wife's life. He got under law enforcement's skin because of this, as Jack had no one to blame for his death other than Rosatti himself and tried pinning blame on Vignerelli, which falls flat immediately due to Rosatti's lawyer backing him up as well. The kicker? Rosatti's prenup stipulated that if his wife cheats on him, she gets nothing in the divorce, and in his will, if he were to commit suicide, Vignerelli gets everything, potentially leading to one nasty legal battle, that of which Mrs. Rosatti could lose, either out of exhaustion from the whole ordeal, or Rosatti's lawyer using the evidence against her already violating the prenup. He made damn sure his wife suffers as much as possible.
* MayDecemberRomance: The detectives refer to this trope by name; Sherri is middle-aged and Randy in his 20s.
* NeverSuicide: Subverted. Tony's death actually ''was'' a suicide intended to frame Sherri and Randy.
* OutWithABang: The victim's first wife comments that she would have expected Sherri to choose this method of killing him.
* ProfessionalKiller: Jamie Astangura is one, and Tony hired ''another'' professional killer since Jamie wasn't available.
** The way Rosatti's body is found leads Briscoe and Green to figure out that a professional killer was involved: no bullet casings, no messy job and no stolen possessions means no apparent personal motive and a lot of experience with murder.