Guest Stars Clark Gregg as Arthur Sackler, Sr. Jack Mulhern as Tyler Kryger Brian Markinson as Howard Udell Sam Anderson as Raymond Sackler Ron Lea as Bill Havens Ana Cruz Kayne as Brianna Ortiz Carolina Bartczak as Lily Kryger John Ales as Dr. Gregory Fitzgibbons Noah Harpster as Dr. Curtis Wright Tyler Ritter as John Brownlee Johnny Sneed as Dr. Tim Cooper John Murphy as Michael Friedman Cody Porter as Dr. Paul Goldenheim Trenna Keating as Deborah Marlowe Stuart Hughes as Tony Maddy Hillis as Molly Dover Co Starring Olivia Markowski as Toddler Kaylee Vivienne Markowski as Toddler Kaylee David Tompa as Conference Room Lawyer Laura Cilevitz as Richard's Secretary Tara Samuel as Diane Shnitzler Megan Vincent as Carol Brewster Kathryn Bellamy as Tanya Billy Smith as Sheriff Wayne Carson Durven as Scoop Tatiana Deans as Young Rep #2 Kip Weeks as Jack Errol Gilmour as Dealer Bethany Jantzi as Reporter at Cooper's Kayla Gallimore as Young Rep #5 Jaylen Roberts as Young Rep #4 Kyla Dewey as Young Rep #3 Dallas Chorley as U of C Recruit #5 Sonya Goertzen as U of C Recruit #4 Sarah Curd as U of C Recruit #3 Aurelie Renout as U of C Recruit #1 Joe Wynne as Roger Anthony Jhade as Sheriff Baker Timm Zemanek as Hershel Scott Wickware as Kenny Lexie Galante as Young Rep #1 Anthony Gerbrandt as Sheriff Dickerson Joanette Connell as Scoop's Ex Regan Elizabeth Brown as Sheriff Austin Kayleigh Shikanai as U of C Recruit #2