Robert Taylor Walt Longmire Actor Lou Diamond Phillips Henry Standing Bear Actor Katee Sackhoff Victoria Moretti Actor Bailey Chase Branch Connally Actor Cassidy Freeman Cady Longmire Actor Adam Bartley The Ferg Actor Louanne Stephens Ruby Guest Star John Bishop Bob Barnes Guest Star Louis Herthum Omar Guest Star Karina Logue Susan Parkford Guest Star Zahn McClarnon Officer Mathias Guest Star Rey Gallegos Dan Estes Guest Star Irene Bedard May Stillwater Guest Star Nathaniel Arcand Avo Guest Star Austin Hébert Colton Guest Star Arron Shiver Billy Barnes Guest Star Paul Anthony McLean Garrett Driggs Guest Star Rio Alexander Charles Burnett Guest Star Kristen DeVore Rakes Female Bartender Guest Star Christopher Chulack Director Hunt Baldwin Writer John Coveny Writer