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