From 2001-03 he starred as James Mooney in the CBS legal drama series, The Guardian. Whitfield later guest-starred on CSI: Miami, Castle, The Game, Private Practice, White Collar, Rizzoli & Isles, Body of Proof, Law & Order: Special Victims Unit, The Good Wife, and "Scorpion". He also had the recurring role of Agent Henriksen in The CW series Supernatural from 2007 to 2008, and co-starred in the number of television pilots. Whitfield also featured in Ubisoft's first-person shooter, Far Cry 3 as Dennis who helps Jason Brody throughout the game.