Longbaugh is a drug dealer who had been receiving protection from Boyd Crowder. After receiving a tip from Sheriff Tillman Napier, Quarles poses as a buyer and visits Longbaugh and Parker to rob them.
In "Measures", Quarles shows up posing as an interested buyer. Longbaugh, suspecting the man is a police officer, subtly holds a katana up to his neck in order to scare him. Quarles then begins to ask if the two men worry about leaving their drugs in the open. Longbaugh tells him that the cops come in to search, and no matter where they put drugs, they will find them. Quarles says that where he is from, dealers rip each other off all the time. Parker says that nobody ever steals from them, and Longbaugh quickly becomes annoyed with Quarles's questions and tells him that it's time to do his business and leave. Quarles distracts Longbaugh by asking him how to get the rust stain off his katana, and shoots Parker in the head. Longbaugh jumps onto him, but Quarles strikes him several times in the throat with the sheath of the katana and breaks his windpipe. Stunned, Longbaugh is then finished off with the katana sheath.
- Boyd Crowder: Business associate
- Parker: Fellow drug dealer
- Robert Quarles: Murderer, deceased
- Greta: Neighbor
- "Your questions are starting to get on my nerves brother." - Longbaugh to Quarles in "Measures".
- Longbaugh and his associate, Parker, are a reference to the real names of Butch Cassidy and the Sundance Kid.
|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|