Guest Stars Domenick Lombardozzi as Ralph Capone Margot Bingham as Daughter Maitland John Ellison Conlee as Commodore Louis Kaestner (Younger) Paul Calderón as Arquimedes "Archie" Ortiz Louis Cancelmi as Mike D'Angelo Travis Tope as Joe Harper Maya Kazan as Madel Jeffries-Thompson Marc Pickering as Deputy Sheriff Enoch "Nucky" Thompson Dagmara Dominczyk as Dinah Linehan Co Starring Mike Massimino as Capone Entourage Member Madeleine Rose Yen as Gillian Darmody (Younger) Jordan Lage as Young Leander Whitlock Ryan Dinning as Elias "Eli" Thompson (Younger) Ryan Johnson as Althea Sean Stanco as Bodyguard Sean Bell as Skip Shaun O'Hagan as Mr. Glass Matt Bailey as George Raft Ashley Wren Collins as Hotel Maid Max Von Essen as Paul Muni Bill Cwikowski as tbd Eric Leviton as Boardwalk Barker Ginger Kearns as Irene