Boyd survives the shot to the chest and claims it is a sign from God that he should change his ways. Raylan hesitates to believe him, but Boyd is soon sent to prison, where he spends his time reading the Bible and preaching to convicts.
Season two deals with the criminal activity of the Bennett clan. The matriarch of the family is Mags Bennett, who runs a general store and serves as a local power broker. She uses her sons Dickie, Coover, and Doyle to do her dirty work, such as growing marijuana and intimidating rivals.
She also takes in Loretta McCready, a teenage girl whose father she murdered. Raylan gets involved in the Bennetts’ affairs when he tries to protect Loretta from their influence and uncovers a decades-old feud between the Bennetts and the Givens.
Season three introduces a new villain, Robert Quarles, a Detroit mobster who comes to Kentucky to set up shop and compete with the local criminals. He is ruthless, cunning, and unstable, and has a history of torturing and killing male prostitutes.
He also has a secret weapon: a sleeve gun that allows him to shoot people without drawing his weapon. Quarles allies himself with Wynn Duffy, a slick and sarcastic crime boss who works for the Dixie Mafia. Raylan has to deal with Quarles’ threat while also facing personal issues, such as his divorce from Winona and his strained relationship with his father Arlo.
Season four focuses on a mystery that dates back to the 1980s: the disappearance of Waldo Truth, a fugitive who was involved in a drug heist that went wrong. Raylan finds out that Waldo was part of a group called the “Drew Thompson case”, which involved a parachutist who fell from the sky with bags of cocaine and was never identified.
Raylan tries to find out who Drew Thompson is and why everyone is looking for him, including Boyd Crowder, who wants to use him as leverage against the Detroit mob.
Along the way, Raylan encounters new enemies and allies, such as Constable Bob Sweeney, an eccentric lawman who idolizes Raylan; Colt Rhodes, a former military sniper who works for Boyd; and Ellen May, a naive prostitute who becomes a key witness.
