The 2004 case of a teenager who died while serving time in a juvenile detention boot camp is reopened after new evidence suggests his death wasn't an accident. Scotty had intended to serve as a character witness at the boy's hearing but arrived too late, something he always regretted. Stillman is ordered by his new boss, Deputy Commissioner Pat Doherty, to drop the case and must pay a price when he doesn't. Meanwhile Lilly enlists help from her old flame Eddie Saccardo in her feud with Moe Kitchener.
- Kathryn Morris as Lilly Rush
- Danny Pino as Scotty Valens
- John Finn as John Stillman
- Jeremy Ratchford as Nick Vera
- Thom Barry as Will Jeffries
- Tracie Thoms as Kat Miller
- Jerry Hernandez as Alex Caceres
- Steven Culp as Evan Price
- James Earl III as Ray-Ray
- Christopher H. Fisher as Michael Rogers (2009)
- Miguel Perez as Judge Harold Alvarez
- Adina Porter as Laticia Myers
- Keith Szarabajka as Deputy Commissioner Patrick Doherty
- Becky Wahlstrom as Marci Rich
- Cress Williams as Jimmy Clarke
- Jeremy Ratchford does not appear in this episode.
- Although he does not appear in this episode, Moe Kitchener's first name is revealed to be short for Maurice.
- The revelation of a judge taking bribes to impose unusually harsh sentences on young offenders at a privately-run youth detention facility was inspired by the 2008 "Kids for cash" scandal, in which two Pennsylvania judges were indicted over kickbacks to send young defendents to such facilities.
- Scotty Valens was already in Homicide back in 2004, and not in Narcotics as the episode had showed. Before 2003, he was in Narcotics over at West.
- This is the least watched episode, it averaged 7 million viewers.
- The show started 51 minutes late.
- Moby "In This World"
- Paul Wall "Luv N My Life"
- Talib Kweli "Get By"
- The Roots "Don't Say Nuthin'"
- Solomon Burke "None of Us Are Free"