Guest Stars Matthew Del Negro as Chris Caysen Zoe Margaret Colletti as Benedetta Rohr Blake Baumgartner as Kick Ryan Catherine Wolf as Rose Congemi Sarah Shahi as Rachel Benham Kathryn Erbe as Sue Stanton Michael O'Keefe as Agent Clasby Kevin Dunn as Nathan Rey James Remar as Richie Ryan Rory Culkin as Clay Roach KeiLyn Durrel Jones as Andre Benjamin Cathy Moriarty as Dottie Ryan Cody Kostro as D.J. Joye Sharon Washington as Shirley Hanlon Derek Klena as Tow Lot Guy Merissa Czyz as Annie Melendew Co Starring Nora Murphy as Marie Ryan Grayson Eddey as Tony Ryan Robert Wahlberg as Bernie Hannahan Jack Dunn as Keenan Cole Brandon Tabassi as Joe Nazzarin Jason Iannacone as FBI Agent Nathaniel Beal as State Police Colonel Kyle W. Brown as Rookie Kevin Kevin as Homeless Man Morgan Pereira as Jess Genovese