In "A Murder of Crowes", Roscoe and Jay rough up a fellow henchman who got stiffed in a weed deal by two teenagers. Their boss, Rodney Dunham, orders Roscoe and Jay to kill the man and he sends them off to find the teenagers and the money. They break into Derek Waters's house and prepare to interrogate them until Raylan Givens arrives. Later that night, they kidnap Derek and have him dig up the money that him and Loretta McCready, his girlfriend, buried but it becomes clear that Loretta moved the money behind Derek's back when he can't find it. Before they can execute him, Raylan intervenes and subdues Roscoe with a shovel. Both men warn Raylan that he better leave before Dunham arrives.
In "Shot All to Hell", Roscoe is seen playing poker with Jay and Johnny Crowder when Dunham comes in. Dunham tells them that he's heard Boyd has another shipment coming in, this time from the Mexicans and suggests they hijack that shipment too. Dunham reveals that he heard it from Boyd, and Roscoe and Jay turn their guns on a shocked Johnny, as Dunham apologizes. However, Roscoe and Jay turn their guns on a shocked Dunham as Johnny reveals that he split the money from the first robbery between the three of them, calling it "people power".
In "Raw Deal", Roscoe is briefly seen alongside Jay when he calls Johnny.
In "Wrong Roads", Roscoe and Jay are seen at Dunham's compound when Alex Miller, Raylan and Henkins arrive, looking for Dunham. Roscoe and Jay tell the men that they haven't seen Dunham either, but Miller leaves Henkins to sit on Roscoe and Jay as they leave to find Dunham since he doesn't believe either Roscoe or Jay. The men attempt to mess with Henkin's head by assuring him he is just Miller's lackey, and he tells the men about Boyd Crowder murdering Dunham's men down in Mexico, where they were found with heroin near their bodies. Roscoe and Jay, using the "hammer and anvil" technique, knock Henkins unconscious and chain him up to the ceiling so that they can get to Kentucky. Roscoe and Jay interrogate Boyd's bartender, Caleb, who tells them that Boyd is at Audrey's. Roscoe and Jay interrupt the meeting between Ethan Picker, Wynn Duffy, Boyd and Daryl Crowe Jr.. Once Raylan and Miller arrive, Roscoe begins reciting King Lear before he is unlawfully shot down by Miller.
- Rodney Dunham - Former boss
- Derek Waters - Associate, deceased
- Loretta McCready - Associate
- Johnny Crowder - Fomer boss, deceased
- Ali - Fellow henchman, deceased
- Jay - Brother, associate
- Marcus - Associate
|Season five appearances|
|A Murder of Crowes||The Kids Aren't All Right||Good Intentions||Over the Mountain||Shot All to Hell|
|Kill the Messenger||Raw Deal||Whistle Past the Graveyard||Wrong Roads||Weight|