When the warden (guest star Toby Huss) asks Jake to investigate Romero's (guest star Lou Diamond Phillips) drug smuggling operation, Jake and Caleb (guest star Tim Meadows) find themselves caught between the loyalty Jake has sworn to both of them. Meanwhile, Amy is offered a deal by a local mobster who claims he can prove that Hawkins (guest star Gina Gershon) is guilty, but Holt and the rest of the gang think they have a safer plan.