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An overwhelmed cop brings the squad the case of a man who was murdered shortly after winning the lottery. They learn the man's winnings earned him a number of fair-weather friends. Meanwhile, Scotty encounters some trouble in his relationship with Frankie.
- 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
- John Bishop as Marty Bayer
- Taylor Cole as Nikki Atkins
- Mary Elizabeth Ellis as Shelly Reid
- Charlie Hofheimer as George Sweeney
- Sylva Kelegian as Pam Bayer
- Jeff Kober as Jack Dubinski
- Jack Laufer as Roger Weaver
- Louis Mustillo as Walt Strickland
- Zack Ward as Ed Dubinski
- Scotty is hesitant at first to join Vera's lottery pool, calling it "a chump's game", but in "The Hitchhiker", he says he plays the daily numbers every morning.
- Spoon "Underdog"
- The Fratellis "Chelsea Dagger"
- The Twilight Singers "Flashback"
- Cat Power "Lived in Bars"
- Ryan Adams "Two"
- Closing Song: Lucero "On the Way Back Home"