Guest Stars Theo Rossi as Jean Carlos 'Juice' Ortiz Dayton Callie as Chief Wayne Unser Ryan Hurst as Harry 'Opie' Winston William Lucking as Piermont "Piney" Winston Drea de Matteo as Wendy Case Emilio Rivera as Marcus Alvarez Taylor Sheridan as Deputy Chief David Hale Ally Walker as Agent June Stahl Lela Cortines as Ellie Winston Dendrie Taylor as Luann Delaney Tory Kittles as Laroy Wayne John Abendroth as Kenny Winston Olivia Burnette as Homeless Woman Julie Ariola as Mary Winston Sprague Grayden as Donna Winston Ashley Monique Clark as Eviqua Michaels Bjørn Johnson as Doctor Keir O'Donnell as Lowell Harland, Jr. Derwin Jordan as Agent Smith