- Carolyn's past becomes Raylan's present; Mansell puts a plan into action.
- Raylan (Timothy Olyphant) wakes up, discovering that he slept with Carolyn (Aunjanue Ellis-Taylor) last night. Carolyn states that they will not mention the event, saying their status quo has not changed at all. As he walks out, he meets Jamal (Amin Joseph), who takes a dislike to Raylan. Mansell (Boyd Holbrook) meets with Sweety (Vondie Curtis-Hall) to discuss any potential targets in the Judge's book. Sweety suggests Burt Dickey (David Cross), a real estate agent in Bloomfield Hills, which Mansell accepts. They visit Dickey and blackmail him into giving up money to have his name removed from the book. Sweety asks for $30,000 but settles for $10,000, infuriating Mansell. That night, Mansell breaks into Dickey's house to retrieve an expensive painting. As the Judge's case has barely made any progress, Downey (Marin Ireland) states that they need to go back to the beginning. Raylan and Wendell (Victor Williams) check on the crime scene but won't find anything through the witnesses and they are unable to reach Detective Raymond Cruz to know more about Mansell. Raylan and Carolyn dine in a restaurant, until their date is interrupted by Jamal, prompting Carolyn to walk out. She later visits Jamal at his house and they appear to reconcile. However, Carolyn discovers that Jamal is dating a woman, which means she no longer has to provide alimony to him. She states that she paid the tax lien and does not want to get involved with him ever again. She then visits Sweety at the Tavern, asking to see the book, willing to cooperate with him to get the position of Judge. Sweety allows her, but tells her not to do anything before informing him. At the bar, Raylan meets with Cruz (Paul Calderon), who claims there is not much information beyond what was found in the file and Raylan asks him what's missing on Mansell, that he "ain't gonna sleep at night that SOB wins." Cruz then tells him a story about a case he solved -- an old case where he went after a criminal who then visited him at home to "have a drink" of beer together. When the criminal was reaching down, Cruz killed him. He was actually reaching for a bottle opener, but the incident was deemed as self-defense, and Cruz says "and I sleep just like a baby."
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