Guest Stars Matthew Del Negro as Chris Caysen Zoe Margaret Colletti as Benedetta Rohr Catherine Wolf as Rose Congemi Gloria Reuben as Eloise Hastings Sarah Shahi as Rachel Benham Kathryn Erbe as Sue Stanton Michael O'Keefe as Agent Clasby Kevin Dunn as Nathan Rey Samantha Soule as Michaela Freda Rory Culkin as Clay Roach Scott William Winters as Todd Hastings J. Bernard Calloway as Captain Shag Lewis Anna Uzele as Adrienne Bullock Hamish Allan-Headley as Parole Officer Chip Zien as Adam Corso Co Starring Blake Baumgartner as Kick Ryan Nora Murphy as Marie Ryan Grayson Eddey as Tony Ryan Kevin Interdonato as Tony Suferin Charlene Almarvez as Yvette Kaishek Akim Black as Leonard Jensen Eric Scott Ways as Ziba Pippin Tara Westwood as Andrew Goodwin Michael Sean McGuinness as Oliver Rawls Lenore Wolf as Greta Roach Jesse Sharp as Foreman Katie Bowler as Party Girl Becca Q. Co as Haley