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 Jordan Lage as Young Leander Whitlock Madeleine Rose Yen as Gillian Darmody (Younger) Ryan Dinning as Elias "Eli" Thompson (Younger) Sean Bell as Skip Sean Stanco as Bodyguard Ryan Johnson as Althea Ashley Wren Collins as Hotel Maid Shaun O'Hagan as Mr. Glass Matt Bailey as George Raft Max Von Essen as Paul Muni Bill Cwikowski as tbd Eric Leviton as Boardwalk Barker Ginger Kearns as Irene