Guest Stars Zoe Margaret Colletti as Benedetta Rohr Catherine Wolf as Rose Congemi Michael O'Keefe as Agent Clasby Kevin Dunn as Nathan Rey Rory Culkin as Clay Roach Chuck Cooper as Judge Rolf Harper Co Starring Blake Baumgartner as Kick Ryan Grayson Eddey as Tony Ryan Nora Murphy as Marie Ryan James Michael Cummings as Tommy Hayes Charlene Almarvez as Yvette Kaishek Robert Wahlberg as Bernie Hannahan Charles MacLean as Scott Hook Lucas Van Engen as Sheik Sheehan Brandon Tabassi as Joe Nazzarin Ben Hansen as Guard Lenny Clarke as A.D.A. #3 Alan J. Paratore as Heartbreaker's Date Patrick S. Hayes as Off-Duty Detective #2 Patrick M. Walsh as Armored Car Driver Diane Boudreau as Marilyn Tom Driscoll as Man in Bar Gene Amoroso as Baliff Rick Burtt as Cop Colleen Kelly as Woman in Hall Chris McGinn as Court Clerk Julia Hsia as Madam Kaishek David Neal Levin as Mourner #1 Michael Malvesti as Brinks Guard #1 Brian A. White as Off-Duty Detective #1 Emilio Cuesta as A.D.A. #2 Lewis D. Wheeler as A.D.A. #1 Owen Burke as Stevie Burke Lance A. Williams as Dealer Kate Avallone as Liz Imperi Susanna Frazer as Widow Thomas Rhett Kee as Brinks Guard #2 Anna Rizzo as Heartbreaker