Guest Stars Carolina Bartczak as Lily Kryger Jack Mulhern as Tyler Kryger Brian Markinson as Howard Udell Clark Gregg as Arthur Sackler, Sr. Sam Anderson as Raymond Sackler Ana Cruz Kayne as Brianna Ortiz Ron Lea as Bill Havens John Ales as Dr. Gregory Fitzgibbons Noah Harpster as Dr. Curtis Wright Tyler Ritter as John Brownlee John Murphy as Michael Friedman Cody Porter as Dr. Paul Goldenheim Joel Keller as Rick Mountcastle Austin Strugnell as Randy Ramseyer Co Starring Olivia Markowski as Toddler Kaylee Vivienne Markowski as Toddler Kaylee David Tompa as Conference Room Lawyer Jamaal Grant as Shawn Flowers Megan Vincent as Carol Brewster Krista White as Mary Jo White Emidio Lopes as 7-11 Cashier Ned Van Zandt as Rudy Giuliani Christopher Morris as Paul Pelletier Al McFoster as Bailiff Lia Luz as Courthouse Protestor #2 Frank Moore as Judge James Jones Stephen Sparks as Howard Shapiro Evan Sabba as Brad Andre Johnson as Courthouse Protestor #6 Randall Triggs as Dr. Triggs Michael Crawford as Courthouse Protestor #1 Linda Preston as Courthouse Protestor #3 Frank Schiavone as Courthouse Protestor #4 Leonia Thames as Courthouse Protestor #5 Gurnam Bhinder as Courthouse Protestor #7 Rosie Callaghan as Richard's Maid Vincent Canning as Junkie Paul Bulicek as Concerned Citizen