In "Harlan Roulette", He is recruited by Johnny Crowder to help the Crowders take control of crime in Harlan County. He poses as a customer in Buck Mulligan's bar. When Boyd Crowder comes to extort ownership of the bar from Mulligan he provides back-up and disarms Mulligan's men when they draw their weapons.
In "Measures", he accompanies Boyd when he vists Tillman Napier and assists Boyd in forcing Napier to help them trap Quarles after Quarles kills Parker and Longbaugh (two drug dealers that Boyd had been offering protection, and Quarles had killed after a tip from Napier). After Boyd manages to lead Quarles into a trap and tase him unconscious, Boyd orders Jimmy to chain Quarles to the bed.
In "Coalition" Jimmy goes into the back room at Audrey's to find a high Quarles, Cat, and Minerva. Jimmy says that there are customers waiting, but gives the women and Quarles five more minutes after Quarles pleads. Cat finds herself with Quarles's chain around her neck, and Quarles orders Minerva to call Jimmy inside. Quarles escapes, but bonds the three of them together. Raylan Givens soon discovers the three who have no idea where Quarles is headed, and Raylan leaves the three of them chained together after saying that they are better off that way.
In "Hole in the Wall", Colt comes into the bar looking for Boyd. Both Johnny and Jimmy deny knowing who Boyd is. Colt, however, notices that Jimmy is a bad liar just from reading his eye movements (something he learned from his days as a military police officer).
In "Truth and Consequences", Jimmy and Colt are sent to Billy's tent after Cassie rejects Boyd's bribe. The two hear hissing, and Jimmy is ambushed by several of Billy's snakes, once of which latches onto his cheek. Colt takes Jimmy back to the bar, with the decapitated head of the snake still attached to his cheek. A doctor is called to check him out.
In "Peace of Mind", Jimmy and Colt argue over what should be handled first: Johnny's betrayal or the search for Ellen May. Later, he is keeping guard at the bar when Raylan and Rachel Brooks arrive. Raylan punches him in the stomach and forces him to call Boyd, but Boyd ends up calling anyway. Raylan and Rachel overhear that Boyd is headed to the church where Ellen May is via speaker phone.
In "Ghosts", Jimmy helps Boyd retrieve a body from the cemetary to swap out with Delroy Baker's to avoid incarceration. While on the way to dispose of the body with Ava Crowder, she makes him get out and he heads back to the bar.
- Boyd Crowder: Boss
- Johnny Crowder: Boss
- Arlo Givens: Criminal associate
- Devil: Criminal associate, deceased
- Rip Bell: Criminal associate, deceased
- Buck Mulligan: Extortion victim
- Shitkicker: Rival thug
|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|
|Season four appearances|
|Hole in the Wall||Where's Waldo?||Truth and Consequences||This Bird Has Flown||Kin|
|Foot Chase||Money Trap||Outlaw||The Hatchet Tour||Get Drew|
|Decoy||Peace of Mind||Ghosts|