Quarles's father was a heroin addict who pimped Quarles out to other men. Once Detroit crime boss Theo Tonin learned of this horror, he offered Quarles the chance to kill his father, which he did when he was 14 years old. After that, Tonin took Quarles in as a son. Quarles grew to despise his adopted brother Sammy Tonin for his cowardice, and even more so when Theo allowed Sammy to have his inheritance over Quarles. While in Detroit Quarles had a habit of beating male hustlers and even put one into a coma for three weeks. This brought a lot of unwanted attention so Quarles relocated to Harlan County, Kentucky for a new start, getting into the Oxycontin business where he is rivaled by Harlan County career criminal Boyd Crowder, who is also seeking to take over the Oxy market. Quarles is a cold blooded, ruthless killer. Quarles grows addicted to Oxycontin, as revealed in "Watching the Detectives" and seems to take doses of it whenever his plans backfire on him. His adoptive father and boss Theo later calls a hit on Quarles after Quarles threatens to kill Sammy and takes a large sum of cash from Theo.
Quarles was first seen at the beginning of the premiere episode "The Gunfighter", having a meeting with Emmitt Arnett. Quarles represents the criminal bosses in Detroit and demands repayment of a loan from Arnett. Arnett agrees to pay him within 24 hours. Quarles seduces Arnett's secretary Yvette and gives her information to pass to Deputy US Marshal Raylan Givens about a planned meeting between Fletcher Nix and Arnett at a cabstand. Marshals arrest Arnett's driver and seize the payment Nix gives him, leaving Arnett unable to pay. Quarles is focused on taking over crime in Harlan County. At the end of the episode, Quarles, Arnett, and Wynn Duffy meet in Arnett's office. Quarles reveals that he told the Marshals about the meeting and Arnett assumes that he is joking. Quarles, after gulping down wine, seriously tells him "I'm not joking." Arnett asks him why and Quarles explains "You had a good thing going here, Emmitt, but you let go of the rope." Quarles reveals a gun hidden in a sleeve holster and shoots Arnett in the head. Yvette walks in and is also shot in the head by Quarles. Quarles asks a stunned Duffy if he knows him now, to which he replies yes.
In "Harlan Roulette" Quarles meets with Duffy to discuss his business plan: Quarles is going to make fake IDs, medical records, MRIs, X-Rays using computers and printers in order to legitimize corrupt doctors. Quarles tells Duffy they are going to move into Harlan and open mobile trailers with a rotation of doctors filing prescriptions for oxycontin. The addicts in Harlan will get half of the pills at a regular price, while the other half goes back to Detroit for ten times the price.
Glen Fogle calls to inform Duffy that Raylan has questioned him. Quarles tells Duffy to have Fogle attempt to kill Raylan. Quarles reasons that either Raylan will kill Fogle, getting him out of the way, or Fogle will kill Raylan, making it easier for them to continue. Quarles is later seen working on his "Taxi Driver" style sleeve holster (a small handgun attached to a track on a support wrapped around his arm). An enraged Raylan shows up at Duffy's mobile office after surviving the assassination attempt. Raylan orders Quarles to put his hands up and turn around, which he does. Raylan punches Duffy twice, and puts his boot on his throat, revealing that he knows Duffy called the hit on him. He then ejects a bullet from his gun, throwing it onto Duffy's chest, and threatens that the next one will come faster. Quarles counters by asking, "How fast do you think those bullets will be when they're heading back at you?" Raylan pulls out his cell phone, and takes a picture of Quarles before leaving.
In "The Devil You Know", Quarles and Devil have a meeting. Quarles tells him that Tanner Dodd is somewhat of a "talent scout", who looks for criminals who are underutilized in their groups, and Quarles tells him that he knows that he is in second tier with Boyd Crowder, and that the enterprise is going nowhere. Devil tells him they have things lined up, but Quarles begins to go into a tirade to get his point across that sticking with Boyd isn't going to get him anywhere. Devil asks him if he has something better, and Quarles says he guarantees it. Quarles says that he can turn his "shitty little project" into a "money making machine" and he needs the right people. Quarles assures Devil he isn't lying to him, and that it will take Devil getting his hands dirty but the opportunity will only happen once.
In "Thick as Mud", Quarles pays a visit to Boyd, who is in his cousin Johnny's bar. Quarles informs Boyd that he got BOTH of his messages, but Boyd tells him that he only remembered sending one. Quarles says that he insulted an employee of his, and appropriated his product. Quarles offers Boyd a partnership, saying that together they will make more money than they will as enemies. Boyd asks Quarles if he is familiar with the term "carpetbagger", which offends Quarles. Quarles gulps down his bourbon, thanks Boyd for it, and walks away to leave. Boyd informs Quarles that men in three-piece suits have been coming from the North to Harlan for years, and that they always die by the end of summer.
In "When the Guns Come Out", Quarles orders Duffy to find out all the information he can on Raylan so that he knows exactly where to apply pressure. Quarles also informs him that he knows someone in the Lexington FBI has been asking about him, and immediately suspects Raylan. Duffy says "sure thing boss", and Quarles seems to love the idea of being called boss. Duffy goes to leave, and Quarles goes into the back room of the office and begins to brutally assault the man tied to the bed who was shown earlier in the season. Unbeknownst to Quarles, Duffy returned and overheard the screams of pain from the man. Duffy later tells Quarles that Boyd's Oxy clinic was hit earlier that morning, and suspects Quarles was behind it. Quarles reassures Duffy that he wasn't. Duffy says he finds it a coincidence because a few hours later, Raylan shut down their Oxy clinic. Quarles laughs saying "that is awesome" about them losing a clinic but smoking out a dirty Marshal in the process. Quarles tells Duffy there's no way Raylan could have caught onto their clinic without an "inside" lead, and he believes that Raylan is working for Boyd, and declares it a smart play on the latter's part. Quarles soon learns from Duffy that Arlo Givens is a member of Boyd's crew, and appears to be delighted upon hearing the news.
In "The Man Behind The Curtain", Quarles appears at the bar where Raylan has been working as a bouncer in order to stay in the room directly above it. He offers to double whatever amount of cash Boyd is paying since he believes Raylan is working directly for the convict. Raylan, however, does not accept his bribe and Quarles says he understands it but that he now knows where Raylan lives. Quarles informs Duffy that Raylan didn't accept the bribe, but that he is going to go meet up with someone who won't turn them down, and he also learns that his boss Theo Tonin's son Sammy Tonin is coming to visit, much to his displeasure. Quarles holds hostility towards Sammy since Theo left all his inheritance to Sammy, despite Theo feeling that Quarles was better suited for the job. Quarles heads down to the Harlan Sheriff's office and bribes Tillman Napier with a briefcase of money to make Napier look the other way whenever Quarles makes a play to take over the Oxy business, as well to take care of Boyd Crowder and get him out of the way. Sammy suggests that Quarles is wasting his time dealing with a bunch of hillbillies but Quarles tells him that once the Oxy market is secured, it will bring in $1 million each month, and Quarles also asks Sammy for $50 grand, and Sammy agrees to get the money to him. However, Quarles is furious once he realizes that the wire transfer was canceled, and learns that Sammy stopped it because the Marshals were onto him. Quarles tells him that next time the FBI is listening to make sure he tells them that Boyd and Raylan are working together. He soon goes to Tulsa to meet up with Gary Hawkins, the ex-husband of Raylan's ex-wife Winona Hawkins.
In "Watching the Detectives", Quarles, Mike, and Duffy have kidnapped Gary and bring him back to his old house in Lexington. Quarles asks Gary to deliver a message to Raylan, and when Gary asks what message, he is shot once by a silenced pistol. Ellstin Limehouse, Bernard, and Errol visit Quarles at his office and Limehouse informs him that Boyd is backing Shelby for Sheriff. Quarles, however, asks why Limehouse is telling him this, and Limehouse replies that he likes to back the winning team. Quarles then meets Tanner in public. Tanner apologizes profusely for attracting attention from the law, and then promises to do whatever he can to make it up to Quarles. Detective Gerrity soon brings Quarles and Duffy in for questioning, where both men deny the "bullet scenario" ever happening but do confirm Raylan's assault on Duffy. Later, Sammy tells Quarles that Theo's guy in the bureau says that Raylan has managed to dodge the framing and that they cannot have anymore heat on them since they are already being heavily watched by the feds. Sammy tells Quarles that "Its over, you're out" because Quarles is becoming too much of a liability. Quarles, in anger, slings his arm forward causing his pistol on his arm holster to go into his hand, and he points it at Sammy. Sammy informs him that it will be a short and lonely life if he goes through with killing him. Quarles pulls the gun back in and tells him to get out of here. Quarles, in anger, ignores a phone call from his family and takes a dose of Oxy while listening to a preacher on the way to visit Limehouse in Noble's Holler. Quarles says to Limehouse "You said you like to back the winning side."
In "Loose Ends", Quarles meets with Limehouse after their ordeal at Limehouse's holler in the previous episode. Limehouse provides Quarles with a campaign manager, Harvey Jones, who is also the County Clerk presiding over the election for Sheriff. Jones reviews his plans for rigging the vote to Quarles, but Quarles doesn't want to hear any of it and simply wants results.
In "Guy Walks Into a Bar", Quarles is seen celebrating with Sheriff Napier in his office after he wins the election. The conversation soon turns cold as Quarles orders Napier to move his stuff out of his office because he wants an office too. Soon, Harvey and Shelby, show up and Harvey announces that since Napier's estranged sister Hanna is on his payroll, Napier has to relinquish the title of Sheriff to Shelby, since he was the runner-up. Quarles angrily folds up his map and grabs his shot glass before exiting as the three men argue. Boyd, who is sitting with Johnny Crowder outside, says to Quarles, "You know what you are?" Boyd asks. "You are a conquistador, but we are not your savages. And now you get to leave with your life ... I hope you enjoyed your stay and you never forget who packed your bags." Quarles face tightens in a rage before relaxing into a broad smile. Quarles heads to Duffy's RV where he proceeds to take several doses of Oxy. Soon Donovan, a friend of Brady Hughes (the street hustler that Quarles had bound and gagged in the back room earlier this season) shows up and holds Quarles and Duffy at gunpoint. He believes Quarles is responsible for the death of his friend, Brady. Quarles talks the boy down, explaining that his own father was a heroin addict who pimped him out to other men. When Theo Tonin caught wind of this horror, he offered Quarles the chance to murder his old man and a 14-year-old Quarles did just that. So, Quarles explained, he understood Brady only too well and only wanted to "set him free." Wynn watches in horror as Quarles, crying and shaking, lowers Donovan's gun and embraces the boy. Quarles and Duffy soon show up at the dive bar where Raylan resides. Quarles, who is high and drunk, says to Raylan "I'm going to kill you Raylan. Maybe not tonight, maybe not tomorrow, but someday you'll be walking down the street and I'm going to put a bullet in the back of your skull." Raylan shoots his gun into the air as Quarles attempts to leave, orders the other bar patrons to leave and asks Quarles "Why wait?" Quarles and Raylan soon agree to draw, but it is ruined when Lindsey, the barmaid, pulls a shotgun out on him and orders the men to leave. Quarles smiles and exits with Duffy, telling Raylan to remember what he said. Quarles is next seen in a seedy hotel room, snorting Oxycontin and talking to himself. He strips down and heads into the bathroom, where Donovan is bound, gagged, and chained to the toilet.
In "Measures", Duffy worries about Quarles since he had threatened to murder Raylan and is now leaving town for a few hours. Duffy asks what if Raylan comes back looking for him, and Quarles says to simply tell Raylan to wait. Quarles says that he is disappointed in Duffy given his "wild man" reputation in Detroit and now he suddenly wants to bail out. Quarles basically tells Duffy to "man up" before he leaves. Quarles soon shows up at Napier's former office, demanding his money back now that Napier is no longer Sheriff. Napier says the money is spent. Quarles, previously smiling, turns mean. He tells Napier that he will have to find a way to pay up. Quarles suggests identifying a drug dealer sitting on large amount of cash. "And if that person is on Boyd Crowder's payroll, all the better," Quarles seethes. Later he shows up at the house of Parker and Longbaugh, two drug dealers Boyd had been offering protection to posing as an interested buyer. He distracts Longbaugh by asking how he gets the rust spot off of a katana he had been previously holding, and shoots Parker in the head. He beats Longbaugh several times with the handle of the machete and kills him, saying "what a dick" as he cleans the blood off his face with his tie. Later, he takes all of Parker and Longbaugh's drugs and attempts to give them to Limehouse in exchange for a place to lay low for a while. Limehouse refuses, saying that he isn't a drug dealer. After learning Quarles was behind the murder of the drug dealers, Boyd forcefully gets Napier to help them out and bait Quarles into a trap. Quarles tells him he needs a place to stash the drugs, and Napier tells him to go to Audrey's, the bar and brothel which Ava Crowder owns. He walks into a back room at Audrey's to find two prostitutes who believe he is a client (Boyd is waiting in the back room with a taser). Quarles calls Duffy and asks why he hasn't called, and Duffy tells him that he has been busy with the Marshals for two hours. Quarles also knows that there is a bounty on his head, but before he can get an answer from Duffy, Boyd tasers him in the back of the neck. Boyd orders the two prostitutes to strip the unconscious Quarles and orders Jimmy to chain him to the bed.
In "Coalition", as Quarles swims out of unconsciousness, he is naked and chained to a bed in Ava's brothel. The working girls, Minerva and Cat, are playing with the gangster's tricky sleeve gun. Boyd was nice enough to leave a bottle of oxy behind and Quarles offers some to the ladies, who are more than willing to partake. Quarles and the ladies are high on pills and seemingly having a great time. But it's only a short time until Quarles turns serious and manages to choke Cat with the chain that tethers him to the bed. He threatens Minerva and makes her run outside to tell guard Jimmy that Quarles is having "some kind of seizure". The unsuspecting Jimmy walks inside the trailer. Quarles chains the two women and Jimmy together and escapes.
Quarles pays a visit to Limehouse who isn't terribly happy to see the gangster arrive empty handed—again. Quarles offers his services in order to repay his debt. "Tonight Boyd Crowder is going to rob that bank", Limehouse explains. Limehouse also knows that Boyd will do it in his normal way: blowing up something across town as a diversion. Limehouse instructs Quarles to take Boyd out as he exits the bank and retrieve the money. Quarles calls Wynn explaining they have a new lease on life. Wynn returns to his RV to find Quarles waiting, smoking oxy and high as a bleached blonde kite. Limehouse calls telling Quarles that Boyd won't be robbing a bank after all, but that he must pay for his intent to separate Limehouse from his money. Quarles agrees to go to Johnny's bar & kill Boyd. Quarles struggles to get straight before exiting his car. Wynn's thug Mike pulls the cellphone triggering device from his pocket that will set off the bomb planted in Quarles' car, but rather than detonate it, Wynn suggests that they might as well wait to see if Quarles can kill Boyd first. The Crowder cousins watch Quarles from inside the bar before Boyd decides to move matters along, going out with his gun drawn and calling the Detroit gangster out of his car. Quarles exits his car and Wynn, watching from his own car nearby and seeing an opportunity to kill two adversaries with one blast, tells Mike to activate the device. Boyd, who knows his explosive devices, hears the tell-tale sound of the detonator and turns to distance himself from "ground zero" as a shot is fired. Boyd is thrown against a wall by the force of a blast and knocked out. Quarles's back is set on fire before he rolls over a few times to extinguish the flames. He stands up as Tom arrives and tells Quarles to drop his gun. Another shot is fired. Givens arrives to find Tom motionless on his back and Quarles nowhere to be found.
In "Slaughterhouse", Quarles is now on the run since state troopers and Marshals are looking for him after the death of Tom Bergen. Quarles comes across a family of Christians who are camping out in the woods after a rock concert, and holds them hostage while hijacking their van in an attempt to flee back to Michigan. Quarles calls Theo, wanting to come back home and demands to know the price to do so. Theo tells him it is $500,000 ($250,000 that is owed to Theo plus $250,000 for threatening Sammy). Quarles agrees to get the money, and dumps the mother of the family off on the side of the road while keeping the two boys as hostages. Through the youngest son Mitch, Quarles asks Raylan to meet him at a destination in the woods and follow his direct orders there. Once he arrives, Quarles demands his guns and his cell phone, before holding Raylan hostage as they head to Limehouse's holler to retrieve money. On the way there, they are spotted by Errol who was leaving as demanded by Limehouse for betraying him. Raylan and the two boys find Limehouse in the slaughter house. "Mr. Quarles wants to go home," Raylan explains. "He needs some money ... You've been saying you just want to be left alone. Well, I figure this gets it done." So Limehouse reluctantly reaches for a knife and cuts open a large pig hanging from the rafters. Wrapped wads of money fall out. "It's a piggy bank!" squeals Quarles. Limehouse then mentions that he can't believe Givens is going to let Quarles get away with the money after killing a state trooper. "Wait, you think I killed the trooper?" Quarles asks. Raylan now realizes that Quarles wasn't the murderer but before he can find out the truth, Errol pops out from behind a pig carcass and shoots at Quarles. Quarles then fires back at Errol, hitting him. Raylan and Quarles get into a fight with Quarles ultimately producing his nifty sleeve gun. Limehouse takes advantage of the situation and severs Quarles's gun arm from the elbow down with a meat cleaver. Quarles falls to the floor, bleeding profusely, but not before revealing to Raylan that Arlo killed Tom.
- Unknown father: Murder victim
- Unknown mother: deceased
- Theo Tonin: Adoptive father, boss
- Sammy Tonin: Adoptive brother, business associate
- Unknown wife
- Unknown son
- Unknown daughter
- Devil: Associate, deceased
- Doc Stern: Business associate, deceased
- Tillman Napier: Business associate
- Ellstin Limehouse: Business associate, murderer?
- Harvey Jones: Business associate
- Wynn Duffy: Business partner
- Tanner Dodd: Enforcer, deceased
- Gus: Criminal associate, deceased
- Teddy: Enforcer
- Emmitt Arnett: Associate in the Dixie Mafia
- Yvette: Arnett's secretary
- Brady Hughes: Hustler
- Gary Hawkins: Winona's second husband
- Longbaugh: Drug dealer
- Parker: Drug dealer
- Errol: Criminal associate
- "You had a good thing going here, Emmitt, but you let go of the rope." (Quarles to Emmitt Arnett in "The Gunfighter")
- "You know me now?" (Quarles to Wynn Duffy in "The Gunfighter")
- "How fast do you think those bullets will be when they're heading back at you?" (Quarles to Raylan Givens in "Harlan Roulette")
- "You mean the m-m-m-m-Marshal?" (Quarles imitating Sammy Tonin's stuttering in "The Man Behind The Curtain").
- "What a dick!" (Quarles shortly after killing Longbaugh in "Measures").
- "When people will conspire to keep you down, you will reach for the edge. They will lean the heel of their boots on your fingers and you just keep fighting, scratching and pulling. And just when you think you've reached the top of the mountain they changed the rules. So what do you do? You don't quit. You don't run. You don't stick that gun in the back of your throat. You realize that you're wrong. You're wrong in thinking that you had already won. True victory is when you crush your opponent so completely that he realizes he was wrong in opposing you from the beginning. You claw your way back into the fight. And you stand atop the mountain." (To himself, before raping Donovan in Guy Walks Into a Bar).
- "Oh shit, it's a piggy bank!" (Quarles after seeing Ellstin Limehouse cut open a pig carcass full of money in "Slaughterhouse").
- "Can I have an amen... CAN I HAVE A GODDAMN AMEN!" (in "The Devil You Know").
|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|