Dempsey is a detective for the Lexington Police Department.
In "Watching the Detectives", he first comes in contact with Raylan when he pulls up to his and Winona's house where Gary's dead body lies. Dempsey had been unsuccessfully trying to reach Gary and Winona, but Raylan sees Gary's body and says "I thought you said you couldn't track him down". Dempsey suspects that Winona may have been the murderer because exes are the most likely perpetrators in homicide cases. Later, Dempsey and Detective Gerrity show up at the Marshals office after the fingerprints on the bullet casing in Gary's body turn out to match Raylan's. Raylan explains to the two men that the night he met up with Robert Quarles and Wynn Duffy, he disloged a bullet from his handgun and threw it at Duffy's chest. Dempsey says that Raylan throwing a bullet at Duffy and saying "The next one's coming faster" may be the coolest thing he has ever heard in years. Dempsey tells Raylan it's a shame they have to lock him up, and Gerrity leaves to confirm the story with Quarles and Duffy. Dempsey then checks Raylan's handgun for ballistics. Both men deny the story of the "bullet" scenario, and Duffy makes his story seem that he was savagely beat up by Raylan because they couldn't locate Gary, rather than because he knew Duffy called a hit on him. Later, Dempsey informs Raylan that the ballistics wasn't a match, but he is not closing the file.
- Detective Gerrity: Colleague
- Raylan Givens: Deputy US Marshal, suspect
- Wynn Duffy: Interogatee
- Winona Hawkins: Interogatee
|Season three appearances|
|The Gunfighter||Cut Ties||Harlan Roulette||The Devil You Know||Thick as Mud|
|When the Guns Come Out||The Man Behind The Curtain||Watching the Detectives||Loose Ends||Guy Walks Into a Bar|