Deputy U.S. Marshal Raylan Givens is a 19th-century style lawman in . He is a quirky, dedicated marshal who, having committed a justified killing in Florida (he shot a mob hit man who had just drawn a gun on him with intent to kill, although Raylan was hoping he would draw his weapon to give him an excuse to shoot him), has been re-assigned to his hometown in Kentucky.
Having grown up in Harlan County and having spent much of his life trying to escape from it, Raylan is not pleased to be sent back there. Ghosts from his past — including his ex-wife, a former friend now involved in criminal militia activity, a criminal father, and his own persistent anger management issues — all come back to haunt him. With the deaths of his father (Arlo), his step-mother (Helen) and mother (Frances), Raylan and his daughter are the only living members of the Givens family. He is portrayed by series star Timothy Olyphant.
Raylan Givens was born and raised in rural Harlan County, Kentucky, raised by his abusive, emotionally estranged father, Arlo Givens, his mother Frances Givens and his stepmother Helen Givens, Frances' sister. Raylan's childhood was turbulent, mainly due to his out-of-control father who was a career criminal and troublemaker. As a young boy, he would frequently run away and stay at his Aunt Helen's, who was the first person he knew with cable television. When his mother died, Helen later married Arlo. Raylan would become familiar with Kentucky's criminal element through Arlo, knowledge that would later prove useful.
In his late teen years, Raylan worked the coal mines with his childhood friend Boyd Crowder. Crowder's family was also heavily involved in Kentucky's criminal underworld. Raylan is portrayed in flashbacks to this period by actor Danny Wildman.
Motivated by an abusive childhood and an intense dislike of the corruption and crime run rampant through his home town, Raylan left Harlan to attend college using money is then aunt Helen had saved and hidden so that he could "get out". Many of Raylan's childhood friends and family acquaintances would later be the very people he would pursue. During his time with the Marshal's service, he was assigned to several different field offices across the U.S. (one of which was in Texas) and spent time sometime abroad before landing in Harlan. Raylan met and married an attractive court stenographer named Winona. An expert marksman with a handgun and an expert at the fast draw with any pistol as well as an expert with other weaponry, one of his assignments was firearms instructor at the U.S. Marshals' training center in Glynco, Georgia alongside Art Mullen, who would later become his boss. When Raylan was transferred to the Miami, Florida Field Office, Winona stayed behind to put their house up for sale. She then had an affair with the realtor, Gary Hawkins, and subsequently divorced Raylan and married Gary. Raylan spent six years in Miami hunting fugitives, and remains in this post when the pilot episode opens. During this time, he assisted in getting Daryl Crowe Jr. sent to the Florida State Prison.
Early in season 1 Raylan says that he's "been doing this 17 years", referring to law enforcement.
U.S. Deputy Marshal Raylan Givens gets run out of Miami for very publicly killing a cartel drug runner named Tommy Bucks. Out of desire to avoid scandal and fear for Raylan's safety, Chief Deputy Dan Grant transfers him to the Lexington Field Office in Kentucky where his former colleague and new boss Chief Deputy Art Mullen assigns him to investigate his childhood friend Boyd Crowder, now a white supremacist who's robbing banks and wreaking havoc.
Not one to play by the rules, Raylan gets involved with Boyd's former sister-in-law Ava Crowder, and risks compromising the case against Boyd.
Season 2 for Raylan starts off just a few minutes after the events from the season finale of season 1. In The Moonshine Wars, after Boyd pursues the drug lord's wounded niece, he eventually tracks her to the airport, and intends to kill her. Raylan arrives in the nick of time, and tries to talk Boyd out of killing her. Instinctively, Raylan and Boyd shoot the niece's two remaining henchmen, with Boyd being wounded in the process. Entrusting Boyd's safety to a passing trucker, Raylan takes the drug lord's wounded niece into her private jet and flies to Miami. Once in Miami, Raylan takes her to the drug lord's mansion, where he attempts to negotiate with the crime boss, telling him to call off his ordered hit on Raylan, or Raylan will kill him then and there.
Before anything else happens, Raylan's old boss, Dan Grant, swoops in and tells the Miami drug lord that if he doesn't call off the hit on Raylan, that he (Dan Grant) will personally come and kill the drug lord himself. With that settled, Grant offers Raylan his job back, which Raylan turns down, instead saying that he'll go home and sleep. Being forced to take on paper work back at the office, Raylan agrees to accompany fellow Deputy US Marshal Rachel Brooks to Harlan County to apprehend a convicted sex offender by the name of James Earl Dean.
After snooping around Raylan discovers that Dean is employed by the Bennett family, which forces him to talk to the Bennett's matriarch Mags Bennett. With the help of a Kentucky State Trooper, Raylan and Rachel track Dean to a gas station arresting him and saving the young Loretta McCready, who Dean kidnapped.
In The I of the Storm, Raylan is trying to deal with the possibility that his secret affair with Winona might be exposed after accidentally running into Tim Gutterson at a concert. While at the same time Raylan is investigating the robbery of a church tour bus, a front for illegal transportation for Oxycontin, only a few miles away from Bennett territory. It is during the course of the investigation that leads Raylan to Dewey Crowe, who previously robbed the high-jackers of the Oxy bus impersonating as Raylan.
In For Blood or Money, Raylan helps Rachel catch her recently paroled brother-in-law, and during the course of their hunt, Raylan tries to make sure Rachel's emotional involvement doesn't affect the case.
When Raylan gets a tip from Dewey that the Bennetts are into something big, he further agitates the clan by looking into the fraudulent check cashing of the young Loretta's missing father during the episode "Cottonmouth".
Following his shooting in the second season finale "Bloody Harlan," Raylan has been admitted to the hospital at the beginning of the third season premiere "The Gunfighter.. Three weeks later Raylan is back on his feet. While testing his shooting at the range in the Marshal's office, it appears the injury has impaired his accuracy, and his ability to quick-draw. Later that day he questions Boyd Crowder about Mags Bennett's missing money and marijuana. Boyd demands an apology because Raylan did not bring Dickie back to him once he was done with him. They get into a fight and Boyd tackles Raylan through Art Mullen's office window. Boyd is dragged out of the Marshal's office. Art places Raylan on light duty due to his injury. Tim Gutterson asks for Raylan's help when one of Wynn Duffy's men, Fletcher "The Icepick" Nix is suspected of a double homicide.
They visit Duffy in his trailer. Duffy remembers that the last time they talked, Raylan threatened him saying there wasn't gonna be a conversation the next time. Duffy doesn't give them any information. Raylan learns that Nix and Emmitt Arnett will be meeting later that evening at a cab stand through Arnett's secretary Yvette. However, unbeknownst to Raylan, Robert Quarles was behind the information being planted. The marshal's capture Arnett's bodyguard but Nix uses a go-between to make the drop and escapes. When Raylan and Winona get back to his motel room they find Nix waiting for them with a gun. Nix orders Raylan to put his gun along with the holster on the ground. Nix likes to toy with his victims, forcing them to play a game. This involves Nix's gun being sat in the middle of the table and having a witness count down from 10, once the count reaches 1, they both go for the gun. Nix usually stabs the other player in the hand with an ice pick before taking the gun and killing them. Raylan sees through Nix's ploy and pulls the table cloth towards him once they reach 1, causing Nix to lunge and stab the table with the ice pick. Raylan then grabs the gun and shoots Nix in the shoulder.
In "Cut Ties" Raylan realizes that Boyd provoked the fight to get to Dickie in prison. He has the charges against Boyd dropped and moves Dickie into solitary confinement until Boyd is released. Art tells Raylan that Arnett and Yvette are missing and that the carpets in Arnett's office have been removed. Raylan investigates the murder of Deputy US Marshal Bill Nichols, working with his old colleague Karen Goodall, now an Assistant Director of the US Marshals. They discover that one of Nichols' clients in the WitSec program, Walter Vondas, was trying to return to his criminal life by selling information about other witnesses. They realize that he was behind the murder and act swiftly to protect the other witnesses in the program. Raylan moves into Winona's house, which she is trying to sell in order for them to get a new place together.
In "Harlan Roulette" Raylan is called to Harlan by Trooper Tom Bergen when federal fugitive Wade Messer is sighted. Raylan ties Messer to a scheme to exchange oxycontin for stolen goods and links this to Duffy and the Dixie Mafia. Duffy tries to have Raylan killed but his men end up killing one another. Raylan goes to warn Duffy that he will not survive if he makes another move against him. He finds Duffy meeting with Quarles and photographs Quarles using his phone. The case prevents Raylan from attending a property viewing with Winona.
In "The Devil You Know", Raylan and Rachel go to Trumbull where Lance lies to him, saying that Dickie and Dewey assaulted him before escaping in a coroner's van. Raylan believes that Dickie escaped to retrieve Mags's cash, so he pays Loretta a visit and she tips them off that Ellstin Limehouse holds it. Raylan and Rachel attempt to talk to Limehouse, but he refuses to give up any information about the money, and invites the Marshals to eat at the barbecue if they would like. Raylan soon visits Boyd, and tells him a story about how Frances went up to Limehouse's holler to escape from a drunken Arlo, and that Arlo went up after her and attempted to fight Limehouse, who ended up beating up Arlo. Raylan tells him that Limehouse had no recollection of it, and Boyd says that maybe Limehouse has beat up so many white men he doesn't remember Arlo. Raylan soon gets down to business telling him that Dickie and Dewey escaped from Trumbull and that he believes Dickie is after the money. Boyd tells him that he may want to check out Lance, the prison medic. While waiting outside of the motel, he spots Ash Murphy carrying coffee and take out food. The two stare each other down, and Ash attempts to shoot at Raylan, who runs Ash over and sends him crashing to the ground behind the car. Raylan spots Ash back up on his feet, disoriented and attempting to shoot again, and Raylan puts it in reverse and runs over him. Ash's men peel out in a van headed for Mags's store. Ash refuses to give up any information, but after Raylan creates a ruse saying he is unable to get a paramedic cause of no phone service, Ash tells him they are headed to Mags's old store to receive the money. Givens pulls up to Mags's store to find Dickie (seemingly randomly firing a shotgun), and the dead bodies of Combs and Junior. Dickie says that he is clearly the victim, and Raylan agrees.
In "Thick as Mud", Raylan arrives home late to find Winona waiting up for him. She reminisces on the night she was reunited with Raylan when he scared Gary in her kitchen. Raylan says that she is seven weeks pregnant and asks if she is ready to move, and he hasn't lined up a place. Winona tells him she is angry, but she is done trying to change who Raylan is and pretending that she will ever feel the same about any other man that she does about Raylan. Raylan says that might be the sweetest thing she ever told him and they kiss. Raylan is soon called by Rachel, who reports that Dewey was seen fleeing from a motel, and stealing a car at gunpoint. Upon entering the hotel, they find that Lance is missing too. At a strip club, a stripper tells him that Dewey had two incisions on his lower stomach that looked as if he had a kidney transplant because her aunt had the same exact incisions in the same places when she had a kidney transplant. Raylan visits Ash in the hospital, believing him to be in on the plan. After taking Ash's morphine drip control and leaning back against his broken legs, Ash reveals that it was all Lance's idea to harvest Dewey's organs, saying that they would make $50 grand alone for livers and kidneys. Raylan has a conversation with Ash's nurse Layla who tells him that Dr. Boisneau, an arrogant transplant surgeon may have the answers about kidney failure that Raylan is looking for. Raylan successfully negotiates with Dewey, who has taken refuge in a storage room in a mini-mart. Raylan tells him that if he is able to urinate, he still has his kidneys. Dewey is able to urinate, and paramedics are called in to look at him. Raylan learns from Rachel that Ash has died, and re-visits Tyree. A receptionist tells him that Ash suffered from a post-surgery stroke, and she has no idea who Layla is when Raylan asks about her. Raylan visits Layla's house, and tells her he didn't know she was from a transplant center nearby and got her first shift as a nurse soon as Ash was admitted. Layla indirectly confesses to killing Ash by inserting an air bubble into his brain. During the conversation, Raylan is stabbed by Lance in the shoulder with a needle, leaving him unconscious. Lance persuades Layla into letting him harvest Raylan's kidneys. Layla shoots Lance in the chest, and he falls on top of Raylan, who is slowly regaining consciousness in the bathtub. Raylan shoots Layla in the chest through Lance's stomach when she attempts to shoot him. Layla says "I can't believe you shot me" before collapsing to the ground. Raylan expresses shock to Art over shooting a woman, something he has never done before. Raylan arrives home to find it empty with a letter presumably from Winona, and it appears to be bad due to Raylan's reaction.
In "When the Guns Come Out", Raylan is distraught after learning Winona has left him. While searching through Winona's computer in her office, he sees that she has been looking up flights to Costa Rica. The new court stenographer, Mabel, comes in and the two exchange barbs until Mike Reardon comes in. Raylan asks Mike if he has heard from Winona, but he tells him that he hasn't and advises Raylan to leave her alone until she sorts everything out because if he pokes into her personal life, he might find something that he will regret learning. Raylan then goes into the evidence locker where he finds that the money Winona stole in "Blaze of Glory" is missing. Raylan soon goes to his office where Art talks to him about a shooting that happened in Harlan, and he wants Raylan to stop it before it blows over. Raylan interrupts asking for time off due to his mind being scrambled by Winona leaving him. Art tells him that the shootout happened at Helen's old property on the Indian Line. Raylan reluctantly agrees to check it out. Tom Bergen tells him that they could not get any information from Arlo, who only said to direct any questions they may have to Raylan. Raylan visits his father, angrily wanting to know why their family name has been involved in the "clinic" massacre. Arlo tells him that he was only helping out Boyd. Raylan visits Boyd, and threatens him by saying that he doesn't care about Boyd's Oxy business, but the next time his family name is involved, he is going to lose his Marshal's star and come calling. Raylan visits Ava for information after Boyd instructs him to do so, and the two head to Delroy's trailer behind Audrey's to speak to Ellen May. Delroy soon comes in with a knife, and Raylan flashes his badge and gun and orders the reluctant man to wait outside. Raylan soon goes out, and punches Delroy in the face with his gun after he still threatens the Marshal. Raylan orders the man to not let anything happen to Ellen May, and he initially refuses until Raylan kicks the man again. Following Ellen May's lead, he heads over to the clinic that is run by Tanner Dodd. Tanner instructs his henchman, Gus to floor it once the Marshal is inside. Raylan tells him he fits the description of an eyewitness report that killed 3 people in a shootout. Dodd attempts to shoot Raylan, but Raylan grabs his arm, causing him to fire shots at the roof. A fight ensues between the two men with Raylan getting the upper hand until Dodd kicks him off into a table. Dodd attempts to retrieve his gun but Raylan climbs onto him and grabs his arm again, causing him to fire a shot that hits the driver, Gus, in the back of the throat, killing him. Raylan soon throws Dodd, and his gun, out of the car as it is speeding down the road. Raylan asks Bergen if he found anything about Winona from the BOLO. Bergen says he didn't, but tells Raylan the last time they located Winona it was outside of Louisville, so Raylan uses that lead to find Winona at her older sister Gayle's house. Gayle initially refuses to let Raylan see her until Winona tells her it's okay. Raylan suspects she stole the evidence money to go to Costa Rica, but she swears that she didn't. Winona reveals to him she left because she didn't want her baby to be raised in an environment where Raylan is killing criminals, and that if Raylan wanted to change his life around. Raylan realizes that Winona loves him and their child, but she's skeptical on the chance of their relationship lasting.
In "Hole in the Wall", Raylan receives a call from Sharon Edmunds, a bail bondsman and former lover of Raylan's. Sharon offers him the task of bringing in Jody Adair, a man responsible for the murder of two men who recently jumped bail and fled back to Kentucky. Sharon offers him a cut of the profits if he is captured by Lexington officers. Raylan finds Jody at the house of his ex-wife, and captures him by shooting his air bag. Jody's constant talking annoys Raylan, and he puts Jody in the trunk of his car. Raylan soon gets a call from Constable Bob Sweeney about the vandalism in his house. In the wall, Raylan finds a mysterious canvas bag with a driver's license inside. The two teenage vandals, Roz and Benny, watch from afar as Raylan throws the bag into his trunk. At a hardware store, Roz walks inside and flashes Raylan to distract him long enough for Benny to steal his car. Raylan finds it at a junkyard, seeing that Jody and the bag of money are missing. Raylan finds Jody, Roz, and Benny in the office and Roz points a gun at him. Jody pleads for her to shoot him, and Raylan offers the teens a chance to plead only to car theft, if she hands him the gun. The scrap yard owner, Henry, has overpowered Bob and holds him at gunpoint in the room. While going to retrieve money from Raylan's wallet, Raylan hits him in the face, and Jody holds Roz hostage. Bob stabs Roz in the foot, and Raylan is able to subdue Jody by hitting him with a tire rim during the distraction. Back at Arlo's, Bob realizes that Raylan only needed his help because he was doing an off-the-book task, and Raylan tells him that he was trying to earn money on the side because he had a baby on the way. Raylan reminds Bob that he was able to save both of their lives. Raylan visits him in prison to question him about the mysterious canvas bag and its contents. Arlo denies knowing what any of it is, including a driver's license issued to a "Waldo Truth". Arlo also denies hiring the two teenagers, Roz and Benny, to raid his house in search of the bag. Arlo, however, slips up in his lie and mentions that Raylan should put the bag back in the wall (A fact which Raylan never disclosed in the conversation). Back at his motel room above the dive bar, Raylan hides his cash in a drawer.
In "Where's Waldo?", Raylan volunteers to sign off on some beer deliveries for Lindsey as the lay in bed after making love. A burly man comes into the bar. Despite Raylan's protest that the bar is closed, he helps himself to a beer anyway. After a brief standoff, the man leaves but throws a shoulder into Raylan in the process, and throws a stool onto the ground. At the Marshal's office, Art informs Raylan of the murder of Sam Porter at the hands of Arlo. Raylan says that the inmate saw Raylan when he went to visit Arlo with the mysterious bag. Raylan confides in Art the bag's contents. Raylan, Art, and Tim stake out the Truth residence, and give chase after Milo, the grandson, when he checks the mail. The whole Truth family comes out, armed with guns. The eldest son, Jud Truth, clearly has no respect for law enforcement. The whole family draws on the Marshals when they threaten to cut off their disability checks. Soon, "Waldo" enters the house and claims to be Waldo Truth, but has no knowledge of the bag or knowing who Arlo is. After being handcuffed, "Waldo" confesses that his real name is Harold Shawn, and that he agreed to keep providing the family with disability checks and that only pretended to be Waldo. Mother tells the Marshals that the real Waldo disappeared with a pilot named Drew Thompson 30 years ago and never came back. At the Marshals office, Art shows Raylan a file that confirms Waldo Truth was the same dead body from 30 years ago that parachuted into Harlan with cocaine as a scar found on his body matched up with a scar on the dead parachutist. Raylan wonders where Drew Thompson is if the dead body wasn't his. At the bar later that night while Lindsey and Raylan are kissing, the man from earlier shows back up. "Buddy, we are definitely closed!" Raylan yells. The man exclaims he is only there to talk to his wife, referring to Lindsey. Raylan is shocked at this revelation.
In "Truth and Consequences", Raylan and Lindsey discuss the recent appearance of Randall. Lindsey confides in Raylan that while her and Randall were married, they developed a scam where Lindsey would get close to a male, find out what he has valuable enough to steal, and that Randall would make his move and pocket the merchandise. However, Randall got too jealous of the attention Lindsey got, causing him to almost beat a man to death and get sent to prison. She reassured Raylan that she has reformed, and they continue making love. At the gym, Raylan meets up with Randall, and notes that part of Randall's probation requires him to stay in Florida. Raylan warns him to pack his things and head back to Florida by 6 PM. Randall challenges Raylan to a fight at that time, which he cooly accepts. Raylan and Tim leave to talk to Eve Munro, a psychic who is the ex-wife of Drew Thompson. The marshals tell her that Drew may not be dead after all. Before they can get any more information, a car belonging to FBI Agent Alex Barnes pulls up and Raylan tells her to hide in a room without a window, only to find her missing. Barnes announces that his organization will be taking over the Thompson case. "The best thing you fellas can do is stay out of my way," he finishes with a smile before exiting the office. Raylan is suspicious that something isn't right. Raylan goes back to the gym, to find that Randall has cleared out his locker and left, seeming to heed Raylan's warning. Outside the gym Givens runs into the FBI agent. Givens notes that the only people who knew he'd be at the gym are Art and Ms. Monroe. So how did the agent find him? "The only thing to do now is to tell us who your partners are before they kill her," Raylan says. The dirty FBI agent slowly raises his weapon. He has no intention of going to prison, or risking the wrath of his mystery employers. "You don't know these people," he tells Raylan. The FBI agent then tells Raylan where he can find Ms. Monroe—a nearby hotel—before putting his gun to his head and pulling the trigger. Later at the bar, Raylan has a talk with Rachel and goes upstairs to find his motel room is trashed, and his money from the Jody Adair task is missing.
In "This Bird Has Flown", Raylan and Rachel visit Joe Hoppus for questioning, and learn that Randall planned on using the stolen money to manage a cock-fighting ring. Raylan and Rachel then visits Patterson Gaines, who was paid to organize a cock-fighting package for Randall. While there, Raylan checks his voice mail and gets a message from Lindsey, where he traces it back to the gas station. The pummeled store clerk, Alvin, IDs the couple and says they were heading for a nearby farm. Before leaving there, Rachel hands Raylan a shotgun filled with bean bag rounds. Raylan finds Lindsey and Randall, and shoots Randall in the stomach with one of the rounds. While Raylan talks with Lindsey, Randall tackles him to the ground and a scuffle ensues. Raylan gets the upper hand, but is shot by Lindsey. Randall is then shot three times before being knocked out by the butt of the shotgun. Lindsey tells Raylan that his money is in the back of the van, but Raylan finds only chickens instead. Randall is handcuffed to the back of the van, where the state troopers will arrive to pick him up. Raylan shoots Randall in the leg after failing to heed his warning. With no place to go, Raylan heads back home where he collapses onto the bed.
In "Kin", Winona meets Raylan before one of her doctor's appointments. He tells her that he is in charge of one of the biggest cases that the Marshal's office has seen, but she doesn't seem too impressed. Raylan leaves before the appointment when he has to deal with work. On his way into the Marshal's office, Barkley confronts him and accuses him of being behind the Drew Thompson case being turned over to the Marshals. Barkley also accuses him of being dirty, to which Raylan replies "Kiss my ass". Raylan is angered to learn that Vasquez is offering Arlo a deal: His freedom in exchange for the location of Drew Thompson. Raylan meets Bob and finds Roz in his car. Roz tells him that she was hired by Josiah Cairn, her step-father, to retrieve the bag from Arlo's house. Raylan visits Josiah, and handcuffs the man to his car, until he talks about Drew. Raylan calls Tim in for backup in case something goes wrong. Raylan walks through the woods to the hills, and holds up his hands when he suspects all is too quiet. Raylan is captured and held hostage in a room along with Boyd, who was also looking for Drew. Raylan and Boyd manage to subdue their captors, but are re-captured when the group's leader arrives with a loaded gun. He plans on executing the two in an abandoned mineshaft, but Raylan temporarily halts him when he says he is related to Mary. Daniel, one of the hills people, fetches Mary, who immediately recognizes Raylan and protests for the hills people not to go through with killing him. Raylan comes in for Boyd's defense when she decides to stick with killing him, saying that if anybody gets killed he'll have to report it all to his bosses at the marshal's office. Before departing, Raylan handcuffs Boyd to a tree and tells Colt his location and to bring a saw. Raylan revisits Josiah and finds his ankle bracelet on the porch. Raylan realizes the man has cut off his foot when he sees blood and Josiah's severed foot on the ground.
In "Foot Chase", Raylan is at the Cairn residence and he is called by Art, who lets him know that they haven't heard back from Arlo's attorney, Sonya Gable regarding the deal. Before departing, Raylan notices a bloody footprint belonging to Roz. Raylan visits Benny and attempts to get him to contact her, which he refuses. Shelby Parlow shows up and resolves the situation, and they find her at the residence of an Indian man named Teddy. Roz denies cutting off Josiah's foot, and when Raylan threatens to expose her sexual relationship with the older Teddy, which would get him arrested for statutory rape, Roz confesses that Josiah made her hide when men arrived, and remembered them calling him "Drew Thompson" before he screamed. Raylan learns that Roz and Teddy were going to kill the men as revenge. Raylan downplays the significance of “Drew Thompson” to Shelby, believing the sheriff to be in Boyd’s pocket, but Shelby protests that he wishes to get out from under Boyd’s thumb, and participate in the Drew Thompson case given Josiah falls under his jurisdiction. Shelby drags a handcuffed Boyd into his office to find a waiting Raylan, and questions him about Josiah Cairn’s kidnapping and severed foot. Boyd denies any involvement given the predicament Raylan left him in earlier by the hills, but Shelby threatens him with investigating another case, such as the missing Ellen May. Raylan and Shelby arrive outside of the Gable residence, observing a Dixie Mafia SUV rolling by, as inside Josiah attempts to delay taking a torch to his foot. Raylan and Shelby enter guns drawn and quickly assume command of the situation. Raylan learns that Josiah had tried to kill him because he wanted to find Drew himself, and he was going to enlist the help of former Harlan sheriff Hunter Mosley to do so. Raylan and Shelby then bond over their newfound trust for one another.
In "Money Trap", Art wants Raylan to offer Arlo a deal in order to learn the location of Drew Thompson, much to his chagrin. He soon learns of the murder of Sharon Edmunds, and heads to the home of Jody Adair's ex-wife, Katrina, for questioning. Instead he finds Jackie Nevada, Katrina's sorority sister. Unknown to him, Jody and his associate, Kenneth, are peering through the window. They were there to retrieve Katrina's stash of money. Raylan takes note of the license plate on Kenneth's car as he goes to leave. Raylan later drops Jackie off back at her home, before noticing the same car from earlier in the driveway, and pulls back in when he realizes something is up. Raylan enters the house to find Jody holding Jackie at knifepoint. Jackie steps on his foot and breaks the hold, but Jody jumps out the window before Raylan can stop him. Jody lands on the roof of Kenneth's car and they speed off. After learning that Kenneth is the owner of the car he noticed, he heads there to find a video from Jody, ominously warning him that he is going to kill him. Raylan heads back to the High Note bar, pulling the fire alarm and orders Kent Chilobeck to send the patrons out, where he sees Jody lying in wait in a booth. Jody believes that Raylan is bluffing and won't kill him as they attempt a draw off. Raylan quickly draws out his gun and shoots Jody to death before he can fire back at him in self-defense. Raylan later sits in Jackie's home and talks to Art when he calls. Raylan visits Arlo at Trumbull to offer a deal to send him to a country club jail if he tells him where Drew is located. Raylan also informs him that Boyd Crowder is helping Theo Tonin locate Drew, and that if they find him first, the deal is nullified. Arlo refuses the deal, telling Raylan to "eat shit". Before departing, Raylan tells Arlo he will be glad when he hears the news if Arlo dies in prison.
In "Outlaw", Raylan visits Hunter at Trumbull, offering him the same deal he gave to Arlo. Hunter is surprised that Raylan is willing to offer him the deal, considering he tried to have him killed. Back at the Marshal's office, Raylan sits with Eve as she goes over DMV photos to identify Drew. Art informs Raylan of his father's stabbing. Raylan visits him in the infirmary, and questions him one last time about Drew's whereabouts. Arlo whispers "Kiss my ass" to Raylan. Later, Raylan stops by Johnny's bar where he sees the Tonin Hitman dressed in the Harlan County Deputy uniform and Boyd in handcuffs. Raylan knows that Shelby gave no such order and guns the man down, killing him when he tries to draw on Raylan. Art tries to give Raylan a week off when he learns of Arlo's death, but Raylan refuses, only wanting to have two days off.
In "The Hatchet Tour", Raylan is in charge of escorting Hunter to a supermax prison by Nelson Dunlop, which angers Art. Raylan reassures Tim that he is only looking for information and that he won't hurt Hunter. Raylan drives to Duffy's motorcoach and questions him, believing that he had Hunter initiate the hit on Arlo, but does inform Duffy that Hunter may be the only person alive who knows Drew Thompson, which interests him. Duffy denies any involvement in Arlo's death. While driving down the road, Hunter jumps out of Raylan's car and attempts to commit suicide by being in the pathway of an oncoming tanker truck, but Raylan pulls him out of the way. Raylan punches the man three times. Shelby soon accompanies Raylan when he leaves to talk to Lee Paxton and Gerald Johns. Both men, however, deny having hired Hunter to kill Arlo also. Raylan learns from Bob that Shelby took the fall for Hunter when Hunter went to look for Henry Crowder so that Hunter could retain his job as Sheriff, and that it was around the same time that Shelby was in mine security. This crucial clue helps Raylan realizes that Shelby is indeed Drew Thompson and that Hunter was protecting him. Raylan, along with other Marshal, wait in Shelby's home for him to enter. Boyd, however, enters the house and is held at gunpoint by the Marshals. It soon dawns on Boyd also that Shelby is really Drew Thompson. Hunter and Raylan have a talk while he is in police custody. Hunter tells Raylan that if he listens to what Frances taught him, he might turn out alright.
In "Get Drew", Raylan, Rachel, and Nick Mooney stake out an airport in hopes of catching Shelby. Shelby, however, suspicious of a stakeout when Ellen May spots a light turned on, orders her to just drive by. At the roadblock, Raylan puts two and two together and realizes that Ellen May is with Shelby after seeing ladies underwear at his house. Raylan and Rachel head to Audrey's to talk to Johnny, who is willing to tip off the Marshals about Shelby's location in hopes that Boyd is incarcerated and out of the way. Raylan, Rachel, Art, and Tim drive to the meeting point and take Shelby into custody.
In "Decoy", Raylan, Rachel, Art, and Tim (along with Shelby) are held up in Arlo's house. Art and Tim soon leave to go to the meeting place for Shelby's transfer, and the remaining three head to the old high school after Art calls Raylan and warns him to leave after coming to the set-up. Raylan, however, rushes back to the house when Bob comes there and finds him brutally beaten on top of Yolo's dead body, and helps him to the old high school. Soon, Boyd and Picker arrive and Raylan refuses to hand over Drew, but urges them to come back with reinforcements (Raylan does this as a way to buy time for Shelby to escape Harlan). Raylan and Bob soon hide in the Principal's office when Boyd, Picker, and the backup return. They learn that Drew has left a while ago while they were gone.
In "Peace of Mind", Raylan talks to Winona on the phone as she wants him to sign paperwork before the birth of their unborn daughter. Raylan walks into the Marshals office, where he is lauded for his capture of Drew Thompson. Raylan and Art learn that Shelby refuses to go through with his deal for WitSec until he knows for sure that Ellen May will be safe and protected as well. Art still shows interest in suspending Raylan, but Raylan argues that he wants to finish what he started and wants to look for Ellen May. Raylan, Tim, and Rachel head to Limehouse's holler where he denies Ellen May is anywhere on the property and dares them to search the property. Raylan orders Tim to stand guard while he and Rachel head to Johnny's bar to look for Boyd. Raylan finds Boyd's associate, Jimmy, and punches him in the stomach and forces him to call his boss. Boyd, however, calls and Raylan tells Jimmy to put it on speaker phone. Raylan and Rachel learn that Boyd is headed to the church where Ellen May is. Raylan arrives after the shooting and takes Ellen May into custody, where he reunites her with Shelby at the Marshals office.
In "Ghosts", Raylan shows up at Winona's house to find Cobb, Lex, and Dominic there. The three men have taken Winona hostage to use her as leverage so that Raylan will help them get to Drew. Raylan manages to dispose of the three men. Art warns Raylan to not bother coming into work if he goes after Nick Augustine since the case is personal due to the threat to Winona. Raylan and Augustine later have a meeting in his limo. . Raylan offers Augustine a deal: Turn himself in and promise that he will leave his family alone. Augustine accuses Raylan of making cop threats that he can't carry out, and that once he kills Sammy in Detroit, he will return to kill Raylan's family. Raylan, however, is one step ahead of Augustine and has called Sammy down personally to Harlan. Sammy has his men, along with Picker, execute Augustine by shooting up his limo. Raylan later plasters over the hole in the wall of Arlo's house before departing outside to drink a beer while looking at Arlo, Helen, and Frances's graves.
In "A Murder of Crowes", Art sends Raylan back to Miami in order to investigate Elvis Machado and the missing Coast Guard Simon Lee. Raylan and his partner on the case, Greg Sutter, make a deal with Daryl Crowe Jr. to clear him of his parole if he agrees to hand over Machado to them. Daryl holds up his deal by telling Raylan where to find Machado after he kidnaps Wendy. Machado tries to pull out his gun when the two Marshals corner him about to depart on a small motorboat, but Raylan and Sutter gun him down in self-defense. Later that night, he talks to Winona and the baby on a video chat.
In "The Kids Aren't All Right", Raylan is called down to a police station where Loretta has been calling for him. She was arrested for attempting to sell marijuana to the son of a police officer. Raylan refuses to bail her out, brushes off her pot dealing boyfriend Derek Waters, but meets Loretta's social worker Alison, who he's instantly smitten by. Later that night, Loretta shows up at the Marshals office, asking Raylan what he did because Derek is missing. They find Derek digging holes looking for the money that Loretta hid for Roscoe and Jay, who are both aware Loretta pulled a fast one on Derek and he has no idea where the money is. Before they can kill him, Raylan knocks Roscoe to the ground with a shovel and subdues both men. Raylan finds out Loretta got herself and Derek mixed up with Rodney Dunham. Raylan meets with Dunham and his enforcers, telling them to stay out of Harlan and let go of their foolish beef with the two teenagers. Dunham seems unimpressed by Raylan’s threat, until Raylan reminds them that growing up with Arlo taught him to be ready for anything, and that he could legally shoot down four of Dunham’s men before they even cleared their holsters. Afterward, Raylan drops Derek off at a bus stop, while Loretta opts to remain in the car. By the time they reach Loretta’s home, Raylan realizes that she played him into solving her problem with Dunham after she moved the money without Derek’s knowledge, though she insists Raylan would have helped her anyway. Raylan shares a glass of wine with Alison in his new estate (the former home of Detroit mob accountant Charles Monroe).
In "Good Intentions", Raylan and Alison prepare to make love when the car alarm on Charles's car keeps going off. Raylan goes to check it out to find a man wielding a bat (Henry Granger Sr.) leaning against the car. Raylan believes that he was a goon sent by Monroe to spook him out of the estate, and tells him that the best case scenario for him is jail and to tell Monroe that he didn't scare. At the Marshal's office, Raylan questions Monroe about the goon, which he denies sending anyone to scare Raylan. Art assigns Rachel to stay at the estate with Raylan because of Henry's visit, much to his chagrin. Later, Raylan tells Alison the truth about the man, which she identifies for him by a shamrock tattoo on his neck. Raylan visits Henry, who claims that Alison planted crystal meth in his house to set him up, and took his son, Henry Jr. away. Raylan assaults him with a bat and threatens him to leave Alison alone. Rachel also spins her theory that Henry and Alison could have worked together that night (with Henry being a diversion and Alison robbing something), and that she could be a criminal. Raylan laments that it wouldn't be the first time. Gloria (Monroe's maid and lover) visits the house, and the two marshals catch her trying to steal gold from the office safe. Raylan has Gloria call Monroe and tell him that the safe was empty. He heads out to Duffy's motorcoach and warns him that Monroe is trying to kill him, which surprises Duffy that Raylan of all people would be concerned for his safety. Outside the motorcoach, shots are heard and Mike (Duffy's bodyguard) has gunned Monroe down outside (although he survives).
In "Over the Mountain", Raylan and Tim are assigned by Art to look for Wade Messer when he goes missing, as Messer is a confidential informant giving the authorities info on Boyd Crowder. At Messer's house, they are attacked by a Mastiff belonging to Danny Crowe, who says that Messer is not there and he has been living with him since his flight from Florida. Raylan visits Boyd and questions him about Messer, and Boyd helps Raylan by writing down the number to Messer's burner phone, where Raylan and police officers trace the call to a local bed and breakfast where they find Messer's lifeless body. At Audrey's, Raylan arrives and has a square down with Daryl, ordering them to leave Kentucky but Daryl refuses to do so. Raylan detains Kendal by law for being a minor working at a bar, and Kendal surrenders, despite the protests from his family members.
In "Shot All to Hell", Raylan arrives at Child Protection Services to oversee Kendal's transfer back into Crowe custody. Raylan threatens to reinstate Daryl's parole in order to force Daryl and his associates out of Kentucky. Wendy brushes off the threat, believing Raylan is messing with Kendal's head and that she will file enough injunctions so that Daryl can go wherever he wants. Alison also chastises Raylan for using Kendal in his vendetta against the Crowes. Raylan manages to coerce a detained Picker into giving up the location of Elias Marcos. Raylan and Art head to a shipping warehouse, where Marcos ambushes them with a machine gun. When Marcos reloads the gun, Raylan sneaks behind crates, and catches Marcos off-guard, shooting him in the chest. Raylan, Art and the Marshals also find Theo Tonin hiding out in a crate, succumbing to a gunshot wound to his abdomen. At the Marshals office, Raylan, Art and David have a drink. David congratulates Art on his apprehension of Theo and jokingly calls Raylan a dick. Before departing, he tells Art and Raylan the story about the Kentucky lawman being present at the time of Augustine's murder, and tells them that Picker revealed the lawman was corrupt FBI agent Jerry Barkley. Raylan tells Art for a fact that Barkley was not the one present when Augustine was killed, leaving it open ended as to whether or not Raylan is confessing.
In "Kill the Messenger", Raylan finds Art drinking at a bar and confronts him. Art, not saying a word, coldly stares down Raylan before punching him in the face and departing. At the Marshal's office, Raylan learns that Alison was ran off the road by Danny and he (along with Rachel) set out to find Danny. Raylan arrives at the Crowe residence looking for Danny, and Wendy denies that Danny is present, reminding Raylan that he needs a genuine reason to enter the home and search, before Raylan reluctantly agrees to find Mike, the owner of the house. Raylan learns from Mike at the hardware store that there was a hunting lodge that was a part of the deal. Raylan and Rachel arrive at the hunting lodge, where Rachel subdues Danny and they find Carl inside. Carl lies to the Marshals, claiming that he and Danny are S&M lovers and that there wasn't a kidnapping situation going on. Out on the road, Raylan insinuates that Rachel tagged along so she could brag to Art that she kept Raylan in check, though Rachel counters that she instead hoped Raylan would open up about what caused the two to come to blows. Raylan apologizes, admitting he thinks the world of Rachel, but won’t divulge what happened with Art, given what it might bring down on all of them.
In "Raw Deal", Raylan learns from Nelson that Art has placed Raylan for morning walk-ins. A man named Larry Salmeron comes in the Marshals office, requesting his $250,000 from backgammon winnings that were seized by the Marshals when they arrested Charles Monroe. Raylan reviews the website and informs Salmeron that the Marshals did not seize the website as Marshals was spelled with two L's instead of one. Raylan is later sent to track down T.C. Fleming, the hacker behind the seized screen showing up. Fleming escapes by sliding down a light pole, where he flips off Raylan. Later that night at a bar, Raylan learns from Alison that Wendy had her suspended for two weeks over misconduct with her cases, and that she was asking intimate questions about Raylan. Raylan learns that his credit cards were canceled, and Fleming calls Raylan, revealing that he was the one behind it. Fleming hacks the phones, making the calls seem like they were placed from Kemp's apartment, where Kemp is arrested and Candace is freed. Candace informs the Marshals of Fleming's location, due to his disrespect for her computer skills and his sexist comments. At the Marshal's office, Raylan learns from Rachel that his request to have Daryl's parole reinstated was denied, and Raylan talks to Art and demands to be treated like a US Marshal and is tired of Art giving him shit. Raylan requests to be transferred from Kentucky as soon as he comes back from visiting his daughter in Florida.
In "Whistle Past the Graveyard", Raylan buys Alison lingerie and a bikini, asking her to accompany him to Florida when he goes to visit his daughter, although she is wary of being around Winona. Wendy calls Raylan, asking for him to help her find Kendal who left with his father, Jack Anderson, who is also being pursued by a bad man. Wendy offers to have Alison's suspension lifted and tell Raylan everything about her brother's involvement in Mexico. Although reluctant, he helps her at the persuasion of Alison. Raylan and Wendy find Jack, after he calls her admitting he screwed up by fleeing and leaving Kendal alone with Michael. Raylan decides to use Jack as bait to retrieve Kendal, but assures that nothing will happen. Once Michael and Jack meet, Raylan tries to resolve the situation peacefully, until Michael lunges at Jack, forcing him to overpower both men. After Michael and Jack are arrested once Wendy and Raylan find them, Raylan gives Kendal the $2,000 he had been planning to use on his trip to Florida, giving Kendal a motivational speech that in a few years, he can make his own way outside of his troubled family, much like he did with his own father. Wendy thanks Raylan for his assistance, and admits that she knows nothing about her brother's involvement in Mexico, and that she lied so that Raylan would keep helping her, which leaves him appalled. Later, Raylan visits Alison, saying he gave away the money to charity and that once he gets more money, they can take that trip to Florida, but Alison says no and breaks up with him.
In "Wrong Roads", Raylan uses his vacation time to head to Tennessee, where he partners with DEA Agent Alex Miller in his investigation of Rodney Dunham. At the compound, they find Roscoe and Jay, who claim that they are looking for Dunham also, although neither men buy their stories. They eventually find Dunham, who is dying from a gunshot wound, but managed to kill one of his henchman who was holding him hostage by stabbing him in the neck with a pencil. Raylan overhears a conversation between Miller and Dunham, and while suspicious, Miller tells Raylan that Dunham was a confidential information for him for 15 years, tipping him off with information about his rivals in the pot business. Raylan and Miller head back to Kentucky and to Audrey's, where they find Roscoe, Jay, Boyd, Picker, Jimmy, Mike, and Daryl. After the situation is diffused when Miller guns down Roscoe and Jay is arrested, Raylan and Miller part ways. Back at the Marshals office, Raylan and Art once again butt heads over Art's growing hostility towards Raylan. Art informs Raylan that as long as he is in charge, he can act as if Raylan isn't there.
In "Weight", Raylan is hunting for Dewey, after he did a hit and run on Miller. Raylan heads to Audrey's, talking to Daryl and Wendy and looking for Dewey. Raylan notices the briefcase on the table and asks what is inside, with Daryl telling him that it is a box of used condoms. Raylan hits Daryl in the face with the briefcase, and finds counterfeit cash inside. Raylan tells them that he is confiscating the cash until they prove where it came from. In the back room at Audrey's, he finds Mina and Teena, paying them counterfeit cash for Dewey's location, who he calls from Mina's cell phone. At Trumbull, Raylan questions Dickie for Dewey's location, but Dickie offers to give the location in exchange to be transferred to a new prison out of the state, which Raylan refuses. Dickie and Raylan exchange barbs, before Raylan departs, realizing whoever Dickie set Dewey up with will probably tip off Boyd and the Crowes, and he will know exactly where Dewey is. At Audrey's, Raylan finds Danny mourning over Chelsea, and tells Danny not to go any further with the duffel bag beside him to Audrey's. Danny challenges Raylan to the "21 foot rule" and charges him, only to fall into a hole that was meant for Chelsea's body, accidentally stabbing himself in the neck with his knife. Raylan talks to Art about Alison, worried that the Crowes might be coming after her. Art says that he will take care of it, refusing to let Raylan help as Raylan has his "foot far enough in this shit heap".
In "The Toll", Raylan is driving Art's wife Leslie to the hospital after his shooting where they discuss Winona before the subject is changed, with Leslie questioning why Raylan wasn't there with Art to prevent his shooting. At the hospital, Raylan wants to investigate Daryl as the possible shooter, as Daryl would probably be looking for revenge because of Raylan causing Danny's death, but Rachel and interim Chief Deputy Ed Kirkland from Detroit, would rather investigate Theo. Raylan talks to Picker in a holding room when he is arrested, and says that Theo signed an affidavit, fingering Picker as the shooter. Picker questions why Raylan would think he would have been working with Theo, as he sent someone down to Kentucky to kill him, and says that the name he heard was Daryl. Wendy calls, saying that Daryl wants to turn himself in and will only talk to Raylan, although this is just a ruse to get Raylan away from Daryl so that he won't shoot him on sight. After Kendal "confesses" to the shooting and Daryl departs to leave on the elevator, Raylan deducts that Daryl had Kendal take the fall for him, as Daryl shot someone and didn't realize it was a US Marshal until the news story the next day. Daryl denies such an accusation, and Raylan threatens to strangle him with his web of lies, and Daryl counters with a threat of his own before the elevator doors close. Raylan goes back to the hospital and takes over the shift of watching over Art from Nelson Dunlop.
In "Starvation", Raylan, Rachel and Tim enter the motorcoach of Duffy and detain both him and Boyd, hoping that they can get their cooperation with bringing down Daryl. Boyd, speaking on Duffy's behalf also, refuses to help the Marshals, who then have Duffy's motorcoach impounded. Raylan visits the Kentucky State Women's Prison, hoping that Ava will help Raylan use Boyd to bring down Daryl. Ava tells Raylan that her and Boyd broke up and that even if she could help, she wouldn't and leaves. Boyd eventually turns himself in at the Marshal's office, and proposes that he can help Raylan catch Daryl by going to the place where the heroin is being stored, in exchanged for a clean slate. Raylan is reluctant to have Daryl arrested on drug possession, but eventually gives in as it is a shot to bring down Daryl. The Marshals stake out the old barn in Loyal, only to find Wendy is there collecting the heroin for Daryl, who knows the Marshals would follow him and they arrest her. Raylan tells Boyd that it's time for Plan B and that he has to wear a wire and get Daryl's confession that he shot Art on tape. This plan also backfires as Dewey interrupts the meeting between Daryl and Boyd at Audrey's and takes the duffel bag of drugs, where he is arrested. After exhausting their options, Raylan and David Vasquez conspire with Mike Reardon to have Kendal tried as an adult for the attempted murder of a federal officer, where he will receive a mandatory 40 years to life sentencing. A stunned Wendy asks who was behind the sentencing, and Raylan confirms it was him before walking away.
In "Restitution", Daryl once again threatens Raylan as he is escorted out by the Marshals. Raylan goes to talk to Kendal in a holding cell, as they bond over stories about having to kill for the first time. Raylan then reveals to Kendal that he is going to be tried as an adult for the attempted murder, although Kendal still sticks to his story as the shooter. Outside of the holding cell, Raylan talks to Wendy, wanting her to wear a wire to tape Daryl's confession, although she refuses as Daryl would kill her if he got suspicious. Raylan enters into Audrey's to find Wendy holding a gun to Daryl's groin after taping his confession to being the one that shot Art. Raylan doesn't stop Wendy as she shoots Daryl in the groin and in the side of the neck, as he leans over Daryl's body as he bleeds to death, and says "Didn't I tell you, you were gonna wish I killed you? Well, don't ya?" Raylan, Tim and Rachel visit Art at the hospital, who reveals to Raylan that Dan Grant (Raylan's former boss) called and said that there was a spot open in Florida, a day after Art set Raylan's request for a transfer from Kentucky. At the Marshal's office, David Vasquez talks to Rachel, Raylan and Tim, wanting to help bring Boyd down in a RICO case, and Raylan easily agrees to help before his transfer. As part of the case, Raylan has Ava released from the prison, who agrees to turn on Boyd to help them. Raylan threatens to have her thrown back in prison if he believes she isn't playing ball.
In "Fate's Right Hand", Raylan goes down to Mexico to visit him at a bar for information about the heroin smuggling and the dead body of Johnny Crowder. Aguilar refuses to cooperate, insulting Raylan for having no power in Mexico and tells him to get out of his town. Raylan waits for a drunken Aguilar to come outside and climb into his police car, slamming into the car with his own vehicle and apprehending him in the trunk of his car. Aguilar gives Raylan Dewey's name as the witness, which he views as a key element in the RICO case. While working the command post at Arlo's house, a strange man approaches Raylan with a briefcase full of cash on the spot, prepared to buy Arlo's house but Raylan rejects him on the spot. Raylan and Tim learn of the identity of a drug dealer with ties to Boyd (Cyrus Boone) and apprehend him at his home for questioning. Raylan and Tim decide to follow Dewey during Boyd's bank robbery and catch him, but find that his briefcase is full of laundry. Raylan meets with Ava that night on the bridge and gives her a pep talk during a crisis of confidence, mentioning that she is able to fool Boyd because she was able to fool Bowman and he was never suspicious that Ava was going to kill him at the dinner table. Raylan pays a call on Chief Deputy U.S. Marshal Art Mullen, recuperating at home from his near fatal gunshot wound. The problem child has brought Art a fine bottle of aged bourbon, but the man cannot partake. The wise old Chief knows this isn't really a social call about Raylan's daughter being baptized a Catholic, and with no prodding, in general terms Raylan explains his dilemma. Art reaches for the bottle, pours a short glass and refines the problem, pointing out that if Raylan kills Boyd in a confrontation, while that would take care of the Boyd problem, Raylan would lose both his badge and his liberty, and would only see Willa through the glass of a prison visiting room window. He also notes that the "other thing" could happen in a showdown, that the bullet could find him instead.
In "Cash Game", Raylan and Tim question Calhoun Schrier, a real estate agent who owned the safety deposit box that Boyd had robbed at the bank and later discover one of Ty Walker's men, Choo-Choo trailing them but Raylan confiscates his car and leaves him on the side of the road. Raylan is called by Ava to the beauty parlor, as she shows him the ledger and documents she found in her shed. Raylan inadvertently implies that Boyd was setting Ava up as the documents seemed a bit too easily placed in the shed. Another visit to Calhoun causes Raylan to learn from a prostitute Calhoun hired, Caprice, that Calhoun is being blackmailed for money with a blackmail ledger that was stolen from his safety deposit box and learns the person responsible is Boyd, who Raylan eventually talks down at the office. Later that night, Raylan and Tim go to the pizza parlor where he gives Choo-Choo his keys back and suggests that Walker is possibly working for someone else as the boss doesn't typical go door to door, although Walker doesn't mention a name and insists for Raylan and Tim to leave.
In "Noblesse Oblige", Raylan meets up with a drunken Ava as he reveals Vasquez and Rachel to also be present with him. The latter threaten to throw Ava back in prison as she hasn't given them any useful information on Boyd to help with the RICO case. Raylan then decides to visit an old mining buddy named Luther Kent who is an explosives owner with Raylan reading through his log and finding out that some of his Emulex explosives have gone missing (They were stolen by Luther's son Tyler Kent as he had been supplying Boyd with them). Later that day, they intervene when Tyler and Boyd's henchman Earl plan on robbing Luther of Emulex at gunpoint. Raylan then arrests Tyler on Emulex charges and attempts to flip him on Boyd and releases Earl so that he can go running scared back to Boyd. Raylan remarks to Rachel that he hopes he knows what he is doing.
In "The Trash and the Snake", Raylan meets up with Ava in the stairwell of a hotel as she informs him about Boyd and her being threatened by Avery Markham, who Raylan describes as "the big bag wolf". Raylan and Tim learn that Markham is attempting to seize the properties in order to profit the weed business he is bringing to Harlan and that an elderly couple, the Hutchins, were murdered and their names were in the book. After finding out that Loretta bought the Bennett property from Dickie (using an alias), they arrive there to find Ty Walker present as Loretta rejects his offer to buy the property. Markham shows up after being called by Walker and has a standoff with Raylan, bringing up his knowledge of Raylan shooting Tommy Bucks when he refused to get out of town. Ava then calls Raylan, panicking that Katherine Hale knows about Albert Fekus and his crisis of conscience and that she has to leave the hotel for her safety.
In "Sounding", Ava calls his phone with more paranoia about her situation with Katherine but Raylan requests that she meet up with him to discuss the case even further and after much reluctance, she agrees to meet him at the junkyard in 30 minutes but instead tosses her phone out of the window and drives to Noble's Holler to make a deal with Limehouse. Raylan calls Bob for help locating Ava under the radar, where he tracks her down from Noble's Holler to a local hardware store where Raylan tells him to get Errol outside of the store and he will sneak in to get Ava out. Bob fails to get Errol out of the store, causing a confrontation which results in Errol being tased by Bob and knocked unconscious. Outside, Raylan scolds Ava for going rogue and almost ruining the RICO case against Boyd. Later that night, Ava requests that she wants $100k and to get out of the country, no WitSec. Raylan tells her that he is going to find a place to keep her safe and she kisses him. Ava warns Raylan that Boyd will be back soon but Raylan suggests that he might stick around a bit.
In "Alive Day", Boyd comes home and finds Raylan waiting there for him, as Raylan mentions he is looking for Dewey Crowe, who was supposed to meet him for information about Mexico. Boyd mentions how Raylan was supposed to be transferred to Florida but yet is still remaining in Kentucky, wondering if there is something he is having a hard time letting go of while he caresses Ava's leg. Raylan and Tim then begin investigating Calhoun's murder after two detectives call them when they find that Calhoun had a Marshals calling card in his pocket and wonder what he was doing with it on him. Raylan causes discord in Markham's camp by visiting him and investigating Calhoun's murder, bringing up the fact that Choo-Choo is nowhere to be found. Walker and two of his henchman prepare to execute Choo-Choo, but are intervened by Raylan and Tim. A shootout ensues, but Walker manages to escape although Raylan fires his gun at him. Choo-Choo is riddled by bullets from Raylan and Tim but manages to escape, only to bleed out later when he stops his car on the railroad tracks as a train approaches.
In "The Hunt", Raylan is pulled away from the manhunt for Walker by a surprise visit from Winona and their daughter Willa who have flown in to Kentucky. Winona mentions that Willa has been having a heart murmur and also that she has a discussion about Raylan having joint custody of their daughter and if he agrees to it, they have to figure out of a plan for who keeps Willa. Raylan offers to take care of Willa when she is fussy from the murmur and Winona is cranky from a lack of sleep due to flying all day. Later, she tells Raylan that the other part of the reason she came back to Kentucky is because that she is still in love with him and that he can still be himself as long as they are together. Raylan kisses her and makes themselves an official couple once again.
In "Dark as a Dungeon", Raylan cleans up at Arlo's house, throwing away clothes, flushing Arlo's medication down the toilet and finding an old footlocker full of items from Arlo's war days such as a machete, letters, photographs and dogtags. Raylan takes it outside and pours whiskey on the footlocker setting it on fire, keeping only a key that was attached to the dogtags. Raylan then talks to a mortician about moving Frances and Arlo's bodies from the house to a new location: Frances' to a local cemetery and Arlo to a potter's field. Tim shows up at Arlo's old house and Raylan tells him that he is going to talk to Zachariah Randolph who has a lead on Boyd. Raylan visits Zachariah, who covers up a crate full of dynamite with a tarp. Raylan wants to know how much Boyd is paying him and punches Zachariah in the stomach before walking inside his house and finding dynamite in the crate. Zachariah punches him in the stomach on the way back out but Raylan gets the upper hand. Raylan tells Zachariah he won't turn him in but either way, he is in deep shit. Raylan finds Markham at The Portal and makes an officer to give Markham his land if he helps him locate Walker. Raylan tells Markham that Boyd is the one who has been telling homeowners not to sell their properties and that they have a common enemy in Boyd with Walker being the man in the middle. Raylan suggests baiting Boyd into a trap with the promise of money and Markham goes onto a local radio show, offering a reward of $100,000 to anyone who can locate Walker. Raylan arrives at Ava's house and Boyd and Raylan have a standoff with threatening to bring the other down before Ava calms the situation down. After Walker has been shot and killed, Raylan takes Boyd to The Portal so that he can collect the $100,000 for collecting Walker. Boyd is suspicious that the whole thing was a trap and that lying comes easily to the both of them. Raylan hears a faint rumbling sound (from Zachariah testing out the dynamite) and takes notice of the vibrating water bottle on a desk near him. Ava visits Raylan questions what she was doing in Bulletville, but she sticks to her story that she was hunting with Boyd and says that Boyd is going up through a busted mine in Blanton Creek. Raylan realizes that Boyd knows about the RICO case and Ava is helping him, tells Rachel that Ava is now burned and that they will hash it out in a morning. Raylan goes to Arlo's forbidden shed and unlocks it with the footlocker key, only to find nothing inside of it. Arlo's ghost is seen as Raylan mentions that he thought everything evil inside of Arlo was inside of the shed.
In "Burned", Raylan is seen with Art, Rachel, Tim and Vasquez as they discuss the possibility of the RICO case being compromised due to Raylan's suspicions that Ava blabbed to Boyd. Art and Raylan visit Duffy in his hotel room in order to talk him into being their second CI in the case against Boyd. Raylan shows Duffy case files which confirm that Duffy was the snitch against Grady and Raylan threatens to expose him to Katherine, causing Duffy to agree to help. Raylan has Duffy tell Boyd that Markham is planning to move the money and Boyd believes that he must break into the vault during Markham's party and Raylan tells Duffy to be present during the heist as well. After Boyd's heist fails due to the dynamite not providing a large enough explosion, Markham and Raylan talk in the basement with Markham saying that he thought they were on the same side but now feels as if Raylan is just using him to get to Boyd with both men replying that they have to do what they have to do as Raylan ponders just exactly what Markham means. Rachel becomes frustrated due to the heist failing and Raylan assures her that they will get Boyd as they will wait for when Markham moves his money because Boyd will just come for it even stronger and stupidly.
In "Trust", Tim and Raylan sit in the motorcoach as Duffy talks to an enraged Katherine who rants about Boyd bombing the floor at The Portal to rob them during the party. Raylan visits Markham at a diner and tells him that he is going to tell Katherine that he is planning to move the money to Charlotte as they believe Boyd has an inside man and that is how they know the exact amount that Markham's vault contains. At the site, Raylan and Tim deduce that Boyd is way too smart to fall for the trap and their thoughts are confirmed when Ava tells him that Boyd is going after Markham's money and not after the decoy truck. Raylan goes to Ava's house and tells her that bad news that Vasquez is pulling the plug on the CI deal and that she is going back to prison, even if he is caught with the money. Ava then asks if they can charge Boyd with the murder of Dewey Crowe, showing him the necklace although Raylan adds that it isn't enough unless Ava can provide a witness, body or a weapon but she offers to get him to confess to Dewey's murder. When Boyd shows back up the house with the $10 million, Ava shoots him in the chest and holds her gun on Raylan, saying that she gave him Boyd bleeding at his feet like he always wanted and that she is not going to prison and that he can either kill her or let her go. Raylan says that he is going to come after her and she says she knows as she flees in Boyd's truck.
In "Fugitive Number One", Raylan visits Boyd in the hospital to find out where Ava could possibly be going with the money and asks if Boyd is okay with the vengeance Markham and his men will dish out to Ava if they find her before the Marshals do. Boyd tells him that Zachariah is the man that they are looking for as he will likely be helping Ava to escape if the mine explosion didn't kill him. Raylan, Tim and Detective Willits find the rescue station but it is empty, although Raylan deduces that they haven't been long gone as the place is still warm and there are drag marks on the floor. Art calls Raylan during the manhunt and says he has to come back to the office now because of Vasquez's belief that Raylan and Ava conspired together as a couple to steal the $10 million and Raylan goes back to Lexington despite calling BS on the accusation. Raylan finds out that Boyd has escaped from the hospital and that Carl has been killed as he views this as more important than going back to the Marshals office. Raylan manages to help Earl out of custody from the dirty cops on Markham's payroll before they can execute him due to Carl's failure to kill Boyd. Raylan visits Markham at The Portal and tells him that he has Earl to testify against him for the attempted murder and that could put him away for a long time. Raylan tells him to lay off chasing after the money and Ava. Avery says he’s feeling at home and is putting down roots with his lady friend and says they’re going to own this town. Raylan says his lady friend is dead as of a half hour ago. He says it went pretty badly in a motor coach owned by Wynn Duffy. He tells Avery all this is on him and says that should guide him as he contemplates his next move and leaves as Avery sits in mourning. Raylan offers Earl protective custody from the Marshals service if he testifies against Markham in court. Earl tells Raylan that he didn't hear anything about the robbery from Ava and Boyd, but does remember hearing them talking about pig shit trucks and someone named Grubes back when Walker was held up in their house. Raylan calls Art and says that he won't be back until he has found Boyd, Ava, the money or all three. Art gives him an extended 48 hours and vows to be the one coming after Raylan as all the other Marshals are preoccupied looking for Boyd.
In "Collateral", Raylan finds Cope in the mountains as he informs Raylan that his people have all been forced further down the mountains due to a search for clean water and that his cousin Mary has passed away since his last visit. Cope tells Raylan that Arlo used the hills people to transport drugs through the mountains because of the blood connection with Mary and that Raylan is a "son of a bitch" for using them just like Arlo. Raylan knocks Cope on the ground before he can do anything and Raylan bequeaths Arlo's property to Cope as compensation in case Raylan is killed while pursuing Boyd. In the cabin, Raylan arrives and argues with Zachariah as he looks for Ava to protect her from Boyd, Zachariah believing that Raylan is no better than Boyd as he's just as guilty of using Ava and messing with her head. Later that night, an intense shootout ensues with Raylan and Boyd, as they both don't know what's in their hearts but the shootout is stopped when the two hear Bob's cries for help after being shot, allowing enough time for Boyd to slip away. Raylan takes Bob to the hospital and turns around to find police officers prepared to arrest him.
In "The Promise", Raylan is first seen in custody by Lapiccola, who is driving Raylan to the police station per request of the BOLO issued by Vasquez. Raylan learns that the KSP Officers are in possession of Dewey's alligator necklace and continues to talk to Lapiccola, who seems to channel Raylan by threatening to put him in the trunk if he doesn't stop talking. Art takes Raylan into his custody at the station and manages to convince Art to let him hunt for Ava and Boyd as Boyd is at large too and that they both know the claims by Vasquez are BS. Raylan and Art head to a bar to talk to Deputy Stiles, who was released from the hospital after being assaulted by Carl. Raylan takes advantage of Stiles' sound sensitivity from the assault by slamming a bat onto the bar counter and forcing him to reveal that Markham is holding Ava captive at the Bennett drying shed.
Raylan comes into the shed and finds that Boyd has killed Birch, Crosley and Markham and kicks him over a gun, challenging him to a gunfight. Boyd refuses to play along and urges Raylan to do whatever he has to do because if he ever gets out of prison, he is going to kill both Ava and Raylan. Raylan turns him over to the police and prepares to deliver Ava, Markham's money and hopefully the remaining $9 million to Lexington when Raylan's vehicle is rear ended by Boon. Boon tells Raylan that he has been following him since he left the drying shed and has saved Raylan the trouble of looking for him. Both men draw their guns and fire, both falling down onto the road. Boon is still alive and reaches over for his gun, but Loretta steps on his wrist to protect Raylan from being killed and Boon dies. Raylan, whose temple was only grazed by the bullet, wakes up to find a nice bullet hole in the middle of his hat and witnesses Ava flooring his car in reverse and fleeing. A stunned Raylan can only mutter "Goddamn it" in frustration. Raylan makes his preparations to leave Kentucky, as he has already caught Boyd and has no reason to stay, saying his goodbyes to Art, Rachel, Tim and Nelson while wearing Boon's hat. Four years later, Raylan is now working in Miami and has a better relationship with Winona, who is now dating a man named Richard and he agrees to pick up Willa after school. Raylan heads to Lebec, California after receiving a newspaper article from Rachel with Ava in the background and finds her new location, still worried about Boyd showing up. Ava reveals to Raylan that she now has a son named Zachariah and that Boyd cannot find out about it. To help Ava and her son be safe, Raylan helps Ava fake her death by showing him a death certificate of Ava's alias, who died in a car accident. Raylan says that the visit was sentimental, despite everything and the one thing he always comes back to is that he and Boyd dug coal together.
Raylan is predominantly driven by deep seeded anger and hatred towards everything related to crime because of his traumatizing childhood with his father. His reason for becoming a marshal was to become the polar opposite of his father in every conceivable way. His methodology to marshal duties runs a very dangerous line between himself becoming an outlaw and continue to living as a law enforcement officer as often mentioned by other characters accusing him of being potentially dangerous as a criminal.
Raylan almost always presents himself to the heads of organized crime in a very direct fashion with no-nonsense warning as soon as they are ascertained as probable suspects. Almost every time when there is an attempt on his life or those of his close companions, he wastes no time delivering guarantee of retaliation. His drive to cleanse criminals within his jurisdiction appear almost obsessive as if he voluntarily looks for criminals to antagonize and fulfill his fix for contempt. Should there be a probable cause for use of lethal force, he does not hesitate to use his weapon. During moments of direct confrontation that often ends up being old western standoff, Raylan presents almost no fear of death and gives matter of fact warnings of his intentions to kill. During the moments of shootouts, while keeping tactical precaution he is not afraid to be out in the line of fire with extreme boldness which helps him end the fire fight very quickly. Art Mullen has acted as his surrogate father and his guide for more controlled law enforcing during his time in Kentucky to defuse Raylan of his never ending rage.
Raylan's personality is very evident in his disdainful language as he does not beat around the bushes when he's declaring his messages to low lives. Even to his family and friends he instills his black and white mantra to handling things. He often throws sardonic jokes that include old school and contemporary pop culture in movies, music, and literature. His facial expression is often scowling or slyly smiling. His body language is almost always relaxed and composed of authority while maintaining tactical precaution whenever he has to. Raylan has a very charming demeanor consisting of a low to medium vocal tone, slowed down speech pattern, and exuberant confidence without a hint of pressure to impress anyone that beautiful women often finds him attractive. He does not doubt or apologize for his apparent badass persona to anyone and owns every bit of it to the fullest extent.
Raylan has and most probably always will maintain his bluntly judgmental view of the world. During his service in Kentucky almost every single criminal tried to deceive him as innocuous individuals and some of them tried to even claim reformation especially Boyd Crowder. Never once Raylan ever entertained the possibility of individuals being any more than their indisputable actions by practically ignoring almost all self-spoken claims of righteousness including those of young Loretta McCready whom gradually demonstrated her own financial greed and disregard for the law. He is an old fashioned man who lives by a strict code which he never breaks: a prototypical alpha male of nearly mythical stature in the modern age. Almost everything about him is left unchanged from start to finish in the show including appearance and demeanor whereas the people around him have moved onto different lives entirely or died. Nevertheless, throughout the series Raylan does grow from an unflinching executioner to a slightly more moderate human being less itchier on the trigger most profoundly influenced by his ex wife and his boss whom even he did not want to disappoint. His deep core is still made up of a good man who respects and loves his compatriots. However, while he becomes less itchier on the trigger, being back in Harlan does cause Raylan to become more ruthless and even cold blooded through the series, most notably when he allows Daryl Crowe Jr to be shot by his sister, and simply asks the dying man if he wishes it had been Raylan who killed him.
Raylan has a strong preference for Western attire—Stetson hat, tailored jeans and cowboy boots. He has a creative approach to law-enforcement. He is a highly skilled marksman with an excellent quick-draw. He also have proven himself quite skilled in unarmed combat with the use of boxing skills. Raylan's approach to crime fighting is similar in style to an old western sheriff, such as accepting a friendly drink from a suspect or witness while on duty. Despite being well known for shooting the most people as a Deputy US Marshal, Raylan is also good at deescalating conflicts by pointing out the weaknesses of a suspect's situation. While he doesn't always follow the rules, Raylan Givens applies himself diligently to putting bad people behind bars and protecting good people.
- Arlo Givens: Father, deceased
- Frances Givens: Mother, deceased
- Helen Givens: Step-mother, aunt, deceased
- Mary: Cousin, deceased
- Heinz, Cousin, deceased (shot by his wife, "Brother's Keeper")
- unnamed uncle (featured in story Raylan relates to Wade Messer, "Harlan Roulette"
- Everett, mother's cousin (owner of an irritable boar, "Cut Ties")
- Willa Givens: Daughter
- Mike Graves, childhood friend "The Kids Aren't All Right"
- Casper John, live-in mate "The Kids Aren't All Right"
- Dan Grant: Former boss and Former Chief Deputy US Marshal of the Miami, Florida Field Office
- Art Mullen: Longtime friend, former boss, Chief Deputy US Marshal for Lexington, Kentucky Field Office
- Tim Gutterson: Former coworker, Deputy US Marshal
- Rachel Brooks: Former coworker, Deputy US Marshal
- Greg Sutter: Current Chief Deputy US Marshal for Miami, Florida Field Office, Partner in Elvis Machado investigation
- Tom Bergen: Kentucky State Police officer, deceased
- Nelson Dunlop: Former coworker, Deputy US Marshal
- Karen Goodall. Former coworker, Assistant Director of US Marshals Service
- Ava Crowder: (Season 1) High school crush
- Winona Hawkins: (Season 1 to Season 3, Season 6 - ) Wife and mother of his child
- Lindsey Salazar: (Season 3 to Season 4) Bartender of the bar above Raylan's former apartment
- Sharon Edmunds: Bailbondsman and former lover of Raylan's from the past, deceased
- Alison Brander: (Season 5) Loretta McCready's Social Worker who first meets Raylan after her client gets arrested for selling drugs.
- Unnamed meth head
- Tommy Bucks: Gun thug out of Miami
- Travis Travers: Kidnapper
- Frank: Hitman sent to kill Roland Pike
- Joe: Hitman sent to kill Roland Pike
- Heckle: Hitman sent to kill Raylan
- Jeckle: Hitman sent to kill Raylan
- Rufus: Accomplice of Bo
- Bo's Man 1: Accomplice of Bo
- Bo's Man 2: Accomplice of Bo
- Ernesto: Nephew of Gio Reyes
- Reyes' Pilot: Shot with Boyd Crowder
- Coover Bennett: Son of Mags Bennett
- Gary's hitman 1: Hitman sent to kill Raylan and Winona
- Gary's hitman 2: Hitman sent to kill Raylan and Winona
- Layla: Nurse who is an accomplice and girlfriend of Lance
- Lance: Prison medic, accomplice and boyfriend of Layla.
- Gus: Accomplice of Tanner Dodd (Accidentally shot by both men during a struggle)
- Jody Adair: Bail jumper and murderer of Sharon Edmunds
- Tonin Hitman: Hitman working for Theo Tonin who impersonates a Harlan County Deputy
- Cobb: Henchman of Nick Augustine
- Lex: Henchman of Nick Augustine
- Dominic: Henchman of Nick Augustine
- Elvis Machado: Drug dealer and associate of Daryl Crowe Jr.
- Elias Marcos: Theo Tonin's consigliere
- Walker Henchman 1: Henchman working for Ty Walker
- Choo-Choo: Accomplice of Ty Walker
- Ty Walker: Ex-Ranger and henchman of Avery Markham
- Boon: Hired gun working for Markham
- Boyd Crowder: Childhood friend, Incarcerated
- Dewey Crowe: Petty criminal, deceased
- Gio Reyes: Leader of the Miami Drug Cartel
- Wynn Duffy: Middleman for the Dixie Mafia, At Large
- Gary Hawkins: Winona's second husband, deceased
- Dickie Bennett: High school basebal rival, Incarcerated
- Robert Quarles: Detroit crime boss, abductor, dismembered, deceased
- Jerry Barkley: Dirty FBI Agent, deceased
- Randall Kusik: Lindsey's ex-husband, Incarcerated
- Nick Augustine: Detroit crime boss, deceased
- Daryl Crowe Jr.: Head of the Crowe family based in Florida, deceased
- Avery Markham: Legendary Kentucky gangster and lover of Katherine Hale, deceased
- (Regarding the shooting of Tommy Bucks) "It was justified"
- "I've shot people I liked more for less"
- (To Ava) - "You do seem to have a penchant for getting abducted"
- (To Duffy's henchman) - "What's wrong with you? You don't piss on someone's lawn."
- "Cause I didn't order assholes with my whiskey." in the episode "Hatless"
- "That's a 10-gallon hat on a 20-gallon head."
- (To Wynn Duffy, dropping a bullet on him) - "The next one will be coming faster."
- "Oh shit, I forgot to bring a knife..." (brandishes holstered sidearm)
- "I'm just gonna file that under 'who gives a shit'." - to Robert Quarles regarding results of the Harlan County Sheriff's election in the episode "Guy Walks Into a Bar"
- (To Art) - "Ever get the feeling God's laughing at you?" in the episode "Measures".
- "You know what your trouble is? You keep thinkin' you're tough. So you're goin' back to prison to be reminded you ain't. You're just...stupid. You're just a stupid, craven, hillbilly piece of shit." - Raylan to Dickie Bennett in the episode "Coalition".
- (To Duffy) - "The S.S. Quarles is going under. You best swim like hell to get clear or the whirlpool will take you down with it."
- "You ever hear the saying "you run into an asshole in the morning, you ran into an asshole; you run into assholes all day, you're the asshole."" - Raylan to Jody Adair in the episode "Hole in the Wall".
- (To Boyd) - "You make me pull, and I'll put you down."
- (To Winona) - "I told him he's got 24 hours to get outta town or I'm a kill him."
- (To Winona) - "Yeah, but he pulled first, so I was justified."
- (Sole statement at US Attorney's review board) - "He pulled first, and I shot him."
- (Regarding Ellstin Limehouse) - "A horsefly sneezes in these hills, he knows about it beforehand, but I'm to believe the car bomb and the dead trooper down the road comes as news."
- (To Duffy) - "The next time we have this conversation, it won't be a conversation."
- (To Dewey) - "Well I might be undertaking a situation here" in the episode "Fire In The Hole"
- (To Roz about Teddy) - "I'm sure you and Rapes With a Smile here were just talking." in the episode, "Foot Chase".
- (To Jackie about Jody) - "He's armed and dangerous, and an asshole." in the episode, "Money Trap".
- (To Art about Jackie) - "Art, this girl ain't the least bit interested in an old fart like me." in the episode, "Money Trap".
- (To Tim) - "Don't say shit unless you know for sure it helps." in the episode, "Outlaw".
- (To Jimmy) - "It's my job, being a dick. It'd be weird if you liked me." in the episode, "Peace of Mind".
- "Well. Now we know each other." (to Nicky Augustine in "Ghosts")
- "Even before I went to Glynco and trained to be a dead shot, I seen people kill one another and I learned to be ready, in case they came after me to do me harm. In other words, I'll kill four of you before you can even clear your weapon, and I'll take my chances with the other two, and you see this star? That's gonna make it legal. Do we have an understanding here?" (To Rodney Dunham and his men in "The Kids Aren't All Right")
- "Miller, would you call this a herd, a gaggle or a flock of assholes?" (To Alex Miller after finding Roscoe, Jay, Boyd, Ethan Picker, Duffy, Mike, Jimmy and Daryl meeting at Audrey's in "Wrong Roads")
- "'Cause that web of bullshit you spun around yourself to protect yourself? I'm gonna use it to strangle the life out of you and take away everything you got. Then you're gonna wish I'd have blacked you out - with a bullet to the head." (Raylan threatening Daryl Crowe Jr. in "The Toll")
- "Didn't I tell you, you were gonna wish I killed you? Well, don't ya?" (To Daryl in "Restitution")
- "I'm not saying she's a Nazi. I'm just saying she grew up near Sukey Ridge." (Talking to Tim about Joyce Kipling in Cash Game)
- "See that? Good things happen to those who wait for stupid." (To Tim while staking about Boyd's crew and seeing Boyd as they prepare for the bank robbery in "Fate's Right Hand")
- Raylan is the only character that has appeared in every episode.
- He likes ice cream, which is an ongoing theme throughout the show.
- He likes Neil Young, although he had to become accustomed to his unique voice.
- He thinks Lynyrd Skynyrd's overrated.
- Raylan has the highest amount of kills in the series with 28 being committed during the show's run and one known to have happened prior to the beginning.
- Raylan was the only character who killed someone in every season.
- Raylan (along with his daughter, Willa) are the only known living members of the Givens family following Arlo's death.
- Raylan, Ava and Boyd are the only characters that have appeared in every season premiere and finale.
- Although, his survival was often credited to his intelligence and quick wit, Raylan also has incredible luck which has saved him on numerous occasions.
- Raylan delivers the final line of the series.
- Raylan never killed the main antagonist of a season. Bo was shot by Cartel snipers, Mags killed herself with poisoned moonshine, Quarles' arm was severed by Limehouse, Colt was shot by Tim, Nicky Augustine was killed by Theo Tonin's men (although Raylan allowed this to transpire), Daryl was shot by Wendy and Markham was shot by Boyd.
- In the final moments of the series finale, Raylan begins to wear Boon's black hat which is more in the style of what Elmore Leonard envisioned Raylan to be wearing.
|Season one appearances|
|Fire in the Hole||Riverbrook||Fixer||Long in the Tooth||The Lord of War and Thunder|
|The Collection||Blind Spot||Blowback||Hatless||The Hammer|
|Veterans||Fathers and Sons||Bulletville|
|Season two appearances|
|The Moonshine War||The Life Inside||The I of the Storm||For Blood or Money||Cottonmouth|
|Blaze of Glory||Save My Love||The Spoil||Brother's Keeper||Debts and Accounts|
|Full Commitment||Reckoning||Bloody Harlan|
|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|
|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|
|Season six appearances|
|Fate's Right Hand||Cash Game||Noblesse Oblige||The Trash and the Snake||Sounding|
|Alive Day||The Hunt||Dark as a Dungeon||Burned||Trust|
|Fugitive Number One||Collateral||The Promise|