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 Kevin Dunn as Nathan Rey Michael O'Keefe as Agent Clasby Rory Culkin as Clay Roach James Remar as Richie Ryan 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 Grayson Eddey as Tony Ryan Nora Murphy as Marie Ryan Robert Wahlberg as Bernie Hannahan Jack Dunn as Keenan Cole Brandon Tabassi as Joe Nazzarin Kevin Kevin as Homeless Man Jason Iannacone as FBI Agent Nathaniel Beal as State Police Colonel Kyle W. Brown as Rookie Morgan Pereira as Jess Genovese