Exactly What It Says on the Tin. The organized criminals of Detroit, united under the leadership of the Tonin family. With connections in Greece, Canada, Tunisia, and of course, Harlan County, Kentucky, the Detroit Mob can make its influence felt anywhere. It is the parent organization for the Dixie Mafia, to which Wynn Duffy and Emmett Arnett belong, and its agents regularly find ways to make life miserable for Raylan Givens and Boyd Crowder.
- The Family That Slays Together: Theo Tonin, his son Sammy Tonin, and his adoptive son, Robert Quarles, are all professional criminals, and all have significant bodycounts to their name.
- Generic Ethnic Crime Gang:
- The mob itself is fairly diverse, but the Tonins are of Greek descent, as are several of their top henchmen, including Mr. Picker and Elias Marcos.
- The Dixie Mafia subsidiary, like the real life Dixie Mafia, is primarily composed of white southerners.
- The Man Behind the Man: Like Gio Reyes and his Miami Cartel, the Detroit Mob tends to work through local operatives, and handpicked buttonmen, as opposed to committing all of its resources.
- Mob War: Thanks to Tanner Dodd and Robert Quarles they end up in one with Boyd. Under Sammy, they go to war with The Canadians, which doesn't go as well for them.
- The Remnant: By Season 5, all that's left of the Tonin's once mighty empire are a few local gangsters under the control of Mr. Picker. With Canada cutting off their drugs, and forced into dependency on Boyd Crowder and Wynn Duffy to stay in business, even they may not last long.
- Ruthless Foreign Gangsters: They're not from another country, but the spirit of the trope is still in full effect whenever Detroit comes to Harlan. The Tonins, Quarles, and Augustine are all far more psychopathic than the local criminals under Boyd, and are much happier to ratchet up the bodycount.
- The Syndicate: Given Theo's worldwide reach, and vast network of operatives, it's fair to say that Detroit comes as close to this trope as a series like Justified can get.
A mobster from Detroit, Theo is the head of the Detroit Mob (the Dixie Mafia's parent organization) and the Tonin family patriarch. He is feared throughout the criminal underworld and his organisation is behind numerous threats to Harlan County in Seasons 3-5.
- Big Bad: Of Season 4. He may remain offscreen and allow Augustine to coordinate the search for Drew, but it's his determination to get Drew that drives the plot, turning Raylan's search for the fugitive into a race.
- The Don: Of the Tonin crime family and the larger Detroit Mob until he flees and Sammy takes over.
- The Dreaded: Theo has such power and sway that everyone is afraid of him; the likes of Wynn Duffy speak to him with reverance.
- Even Evil Has Standards: He took drastic action when he found out what Quarles's father was doing to him and he is seriously disturbed by what Quarles does to male prostitutes.
- Eye Scream: He has a glass eye. According to family enforcer Nicky Augustine, Tonin is after Drew Thompson for not only stealing a shitload of cocaine, but shooting Theo's eye out.
- Framing the Guilty Party: Tries to frame Picker, a fellow career criminal for killing Art. This is most likely payback for Picker killing Sammy.
- Greater-Scope Villain: Of Season 3. Quarles is the immediate threat, and the one who has to be dealt with for the season to end happily, but Theo is the reason why Quarles is so dangerous to begin with, and exiled him to Kentucky in the first place.
- Human Mail: He transports himself in a shipping container when he returns to the U.S. in "Shot All To Hell". He was hit with a stray bullet during the shootout between Marcos, Art, and Raylan. Later, the Marshals discover him when his blood leaks out of the shipping container.
- Kavorka Man: He's shown lounging by the pool with a beautiful, bikini-clad woman in tow. Of course, this is likely to be due to his power and money.
- Non-Action Big Bad: We never see Theo fight, though with men like Mr. Picker, Elias Marcos, and Robert Quarles on his payroll it's not hard to see why he doesn't have to.
- Papa Wolf: Theo was NOT amused when Quarles pointed a gun at his son Sammy, putting a bounty on his head and sending assassins after him. When Picker kills Sammy in Season 5, Theo flies back to the USA to execute him personally.
- The Patriarch: Of the Tonin crime family.
- Revenge: Wants Drew Thompson dead, not only to the protect the organization, but as payback for his missing eye.
- Screw This, I'm Outta Here!: Decides to hide in Tunisia after Drew Thompson goes into custody and leaves the business to his son, Sammy.
- Thicker Than Water: Even though he knows that Sammy is an idiot, Theo still looks out for his son's honor. He did not hesitate to put a bounty on Quarles' head after Quarles pointed a gun at Theo's "real son".
Sammy Tonin is son of mob boss Theo Tonin. He often clashes with Robert Quarles, his father's close associate and unofficially adopted son who is attempting to set up criminal operations in Harlan County. Sammy is short in stature, but isn't to be underestimated.
- Bad Guys Do the Dirty Work: Played with. He has Nicky Augustine killed before Nicky can make good on his hit on Raylan and Winona, but Raylan still set Nicky up to be killed in the first place.
- Bald of Evil: He may be incompetent, but he's still an active member of the Detroit Mob with a great deal of power.
- Boom, Headshot!: He's unceremoniously capped during "A Murder of Crowes".
- Character Death: Mr. Picker shoots Sammy in the back of the head in "A Murder of Crowes".
- Cold-Blooded Torture: In "A Murder of Crowes", when he greets Boyd and Duffy, his hands are covered with blood. The audience can hear a man screaming in a nearby room as a chainsaw roars.
- Conspicuous Consumption: He likes thoroughbred horses, expensive clothes, and fine food.
- The Don: Takes his father's place at head of the Tonin family.
- Dropped a Bridge on Him: He's very suddenly killed by Picker in the first episode of Season 5.
- Even Evil Has Loved Ones: He has a daughter who loves Black Beauty and he's very willing to indulge her.
- Even Evil Has Standards: Sammy is evil, sure, but he's very angry about Nicky targeting Raylan's family, namely a heavily pregnant Winona.Raylan: Sammy's scared of his own shadow 'cause his shadow could kick his ass.Art: Yeah, Raylan, but he's not this, and he's not going to accept Nicky as his number 2.
- Extreme Doormat: He's surprisingly submissive when Raylan confronts him at the horse stables. Even among his henchmen, he's submissive. Picker treats him like a child.
- Friendly Enemy: Somewhat one-sided, with Raylan. In season 4 he's polite to him and even expresses sympathy.
- Grew a Spine: When Quarles points a gun at him, Sammy remains calm and assertive, warning him that his life will be lonely and short if he pulls the trigger. When Raylan comes after him, Sammy assumes he is a hitman and tells him to "tell Quarles I didn't beg."
- Inadequate Inheritor: Subverted; his rivals like Quarles and Nicky all dismiss him as a spoiled weakling, but as of the end of Season 4 he's firmly in control of his father's criminal empire and they are both out of the picture. His inadequacy is proven, however, when he takes control of the Detroit Mob. His poor leadership essentially dismantles a once-dangerous and untouchable criminal empire through sheer incompetence.
- Manchild: He's a spoiled mob prince who hides behind his crimelord father and loves to spend his father's money.
- Noodle Incident: In "A Murder of Crowes", when Boyd and Duffy see a pile of blow-up dolls in his hideout, he tells them, "That was last week."
- Not So Harmless: Quarles and Augustine dismiss Sammy as harmless. At the end of season 4, Sammy shows himself to be anything but. When he learns that Augustine is conspiring against him, he converts Augustine's mooks to his side and has Augustine brutally killed. He also participates in the brutal torture of a Canadian mobster. Him casually walking into the room with blood still on his hands is a somewhat disturbing image.
- Pet the Dog: Despite their terrible relationship, he goes out of his way to warn Quarles that he's risking his life on the Kentucky operation.
- Riches to Rags: In "A Murder of Crowes", we see Sammy and his henchmen operating out of a squalid abandoned building, after their crime syndicate has fallen on hard times due to Sammy's terrible mismanagement of it.
- Rich in Dollars, Poor in Sense: Sammy has always had money, but lacks basic business sense. When it comes to managing the Detroit Mob, he does more damage to the entire organization than law enforcement ever did.
- Sharp-Dressed Man: Subverted. He wears beautiful custom made suits but as Raylan lampshades he does not project the right image and the suits look like they do not fit properly.
- Sudden Sequel Death Syndrome: After successfully taking control of the Detroit Mob at the end of Season 4, Sammy is killed barely a minute into his first appearance of Season 5.
- Surprisingly Sudden Death: Takes over the Detroit Mob at the end of season four, and gets killed with no ceremony whatsoever in the first episode of Season 5.
- The Wrongful Heir to the Throne: Believed to be one by Quarles and Augustine. Subverted in that he is aware of that, so after he takes the reins, he makes sure that most of the crew is already loyal to him. He buys off Augustine's men and gets in touch with Raylan to take care of Augustine before he even flies out of Kentucky. His detractors were proven right post-mortem, however, when Sammy gets into deep debt with the Canadians and endangers the entire organization in a very short amount of time.
Despite his dapper appearance and charming wit, Robert Quarles is a highly unstable and extraordinarily dangerous member of the Tonin crime family. He arrives in Harlan County from Detroit looking for payment on a debt — and then decides to stay a bit longer when he finds potentially fertile ground for his own illegal empire.
He has a tortured and disturbing past — even predating his "adoption" by mob boss Theo Tonin, who considers Quarles to be a son. Quarles is a cold-blooded, ruthless killer who takes particular interest in U.S. Deputy Marshal Raylan Givens after the lawman challenges and, worse, embarrasses him.
- Abusive Dad / Monster Sob Story: Quarles' father pimped him out as a child to get money for heroin.
- An Arm and a Leg: Limehouse severs his arm in the season finale.
- Ax-Crazy: Already highly unstable, Quarles goes completely off the deep end as the season progresses, ratcheting up the bodycount with every sanity point he loses.
- Awesome, yet Impractical: The apparatus requires constant maintenance and if it malfunctions at the wrong time, it will likely get you killed.
- Badass in a Nice Suit: Almost always seen in his suit.
- Badass Gay: Whether Quarles is bisexual or is using his wife to help him stay in the closet, we never find out. Either way, he's got a sexual preference for young men, and is one of the most badass characters in the show.
- Bad Boss: A raving Oxycontin addict and Serial Killer, Quarles is not fun to work for or with.
- Big Bad: Of Season 3.
- Blatant Lies: He keeps telling people that he is unarmed.
- Briefcase Full of Money: He likes to deliver his bribes in those as it proves how serious he is.
- Cain and Abel: With adoptive brother Sammy.
- Chained to a Bed: At the end of "Measures."
- Cheshire Cat Grin: There is something very disturbing about the way he smiles. On the other hand if he stops smiling, you are in deep trouble.
- Daddy Issues: Quarles go so far off the deep end at one point that he asks Wynn "Is daddy getting mad?"
- Depraved Bisexual: He has a wife back home, but also enjoys abusing male hustlers. It isn't completely clear, however, what exactly he does to them, except that it's painful and eventually leads to death. From the tone of the scenes involving Quarles and his captives, it seems to be a question left deliberately open as to whether or not he sexually abuses them. Given what happened to him as a kid it could easily be sexual, or it could simply be Quarles acting on the unimaginable amounts of rage he built up during the time when he was being pimped out by his dad for drug money.
- In "Slaughterhouse," Duffy tells Raylan that Quarles has a thing for young boys, suggesting that Quarles' violence toward his captives had a sexual element.
- Dragon with an Agenda: While he seems to deeply respect the main boss, it is no secret that he hates the boss's son and plans on replacing him as the heir to the criminal empire.
- Drugs Are Bad: Quarles' drug abuse verges on full on chemical dependency, and is very bad indeed, both for himself, and those around him.
- Even Evil Has Loved Ones: He has a wife and children back home. Two episodes have shown him talking to his son on the phone.
- The Exile: From the Detroit mob.
- Faux Affably Evil: He initially appears very charming and even likable, especially after his phone conversations with his son, who he obviously loves very much. Then you get to know him better...
- Final Boss: The first big bad to also be the final physical threat of the season.
- Finger Gun: When he points his finger at you it is actually a serious threat because he has a sleeve gun strapped to his arm and at any point the finger can be replaced by a real gun.
- Fish out of Water: The entire theme of his character. He might be an effective criminal mastermind in different circumstances, but he is completely clueless as to how Kentucky works. Very quickly after his arrival, he is completely outgambitted by Raylan, Boyd and Limehouse; in fact, most of the season deals with his ensuing Villainous Breakdown.
- Freudian Excuse: Quarles' father pimped him out as a child, and he tortures male hustlers in a depraved attempt to process what happened to him.
- From Nobody to Nightmare: Quarles was just a kid, once upon a time, abused and sold by his father. Then Theo Tonin came along, and Quarles ended up being an extremely dangerous mobster.
- Functional Addict: His ability to function while on drugs reaches Made of Iron levels. He consumes Oxycontin like it is candy but still remains clear headed and extremely dangerous.
- Happily Adopted: Played with. Quarles cares about his adoptive father, Theo Tonin, and wants his respect. However, he cannot stand his adoptive brother, Sammy, and his own mental illness and brutality, coupled with his resentment of Sammy, eventually sabotage his relationship with Theo.
- The Heavy: He might have to answer to his bosses in Detroit, but the operation in Kentucky is his and all the chaos that ensues is on him.
- Icy Blue Eyes: His eyes are described as being like those of a husky.
- Katanas Are Just Better: Kills a drug dealer with his own katana.
- Large Ham: He can get very theatrical when trying to prove a point."GIMME A GODDAMN AMEN!"
- Let's You and Him Fight: He sends a group of mooks who were becoming a liability after Raylan. Either they kill Raylan and there is one less meddlesome marshal to worry about or Raylan kills them and Quarles does not have to do it himself.
- Major Injury Underreaction: When Limehouse severs Quarles' left arm with a meat cleaver in "Slaughterhouse," Quarles and Raylan just stare at the severed arm in amazement. He even tries to get it back! Likely justified by the vast amount of pain killers in his system.
- Man of Wealth and Taste: Always turned out in an expensive suit, even at the end.
- The Mentally Disturbed: Quarles should probably be in a mental institution. He's never fully processed his father's abuse of him, and it has resulted in his self-medicating with Oxycontin, with disastrous results.
- Mood-Swinger: Quarles' moods are unstable on a good day, and only get more and more out of control as he spirals further into madness, and becomes increasingly dependent on Oxycontin.
- Morality Pet: His son never appears, but he obviously cares for him very much.
- Motivational Lie: He is very charismatic and really good at using false assurances to motivate people into doing his dirty work. He is not happy when Boyd calls him out on it.
- Mr. Fanservice: Has a brief nude scene in "Guy Walks Into a Bar," as well as a shirtless scene in "Coalition."
- Depending on your perspective, the scene in "Guy Walks into a Bar" could be Fan Disservice, given the scene's disturbing context.
- Nothing Up My Sleeve: Except for a sleeve gun device.
- Quick Draw: He uses a sleeve gun to get the drop on people who think he is unarmed.
- Patricide: In the backstory.
- Psycho for Hire: Once he runs out of options he offers to trade his services as a hitman to Limehouse in exchange for protection
- Rape as Backstory: Quarles' rape by his father's clients directly informs most of his actions.
- Reassigned to Antarctica: While the idea to go to Kentucky was his own, his nastier habits were drawing so much heat that his bosses in Detroit probably were not sad to see him go. When he again draws the attention of the authorities his bosses don't hesitate to cut him off and leave him stranded in Kentucky with no money or support.
- The Resenter: Towards Sammy and anybody else in Theo's favour.
- Sadist: As evidenced by his kidnap and torture of male hustlers.
- Sanity Slippage: As the season progresses Quarles' drug addiction gets worse, his moods become more and more violent, and his ability to maintain even the facade of sanity crumbles.
- Self-Made Orphan: When Theo learned that young Quarles was being sexually abused, he arranged for 14 year-old Quarles to kill his father.
- Serial Killer: Kidnaps, abuses, and kills male prostitutes.
- Serial Rapist: Of the male prostitutes he kidnaps and kills.
- Sharp-Dressed Man: The man really knows how to wear a suit. Becomes even more explicit when he is in the same room as a redneck like Devil.
- The Sociopath: He hits almost all of the requirements for both the disorder and the trope, but it remains unclear how much of his behavior is chemically induced.
- Stepford Smiler: Type C. Quarles looks calm and self-assured on the surface, but is dangerously insane underneath.
- Underestimating Badassery: A lot of people assume that because Quarles is a Fish out of Water he'll be easy to deal with. They're right about him not having a clue how to operate in Kentucky; where they consistently go wrong is in underestimating just how much of a physical threat the man poses, as evidenced by the trail of bodies he ends up leaving behind him.
- The Unfavorite: When he was orphaned he was raised by a mob boss and treated as an adopted son. He always though of himself as the favorite and he is extremely angry that he fell out of favor and the boss's real son took his spot. His main motivation seems to be to become the favorite son once again.
- Villainous Breakdown: Quarles isn't nearly as composed as he appears to be. Quarles quickly spirals downward, crunching Oxycontin pills like sugar cubes, taking out his frustration on male hustlers and watching his big plans for Harlan fall through. Towards the end of season three, Quarles has become a pathetic, desperate man, screaming into his cell phone at Theo, carjacking a family at a camp site and showing signs of Oxycontin withdrawal. This ultimately ends up making him more dangerous rather than less, as he's even more willing to resort to violence.
- Waistcoat of Style: Tends to wear one.
- "Well Done, Son!" Guy: He wants to show the mob boss who raised him that he is the best choice to take over the business.
- Would Harm A Child: Kidnaps a woman's children when he steals her car, and is more than willing to hurt them.
- You Are What You Hate: As a child, his father forced him into prostitution. As an adult, his violence toward male hustlers may represent his own self-hatred.
- You Have Outlived Your Usefulness: He has big plans for Harlan County and he has no qualms killing any mook or pawn that is not useful in furthering those plans.
Detroit Mob Leadership
Nick 'Nicky' Augustine
Nick "Nicky" Augustine is one of mob boss Theo Tonin's go-to henchmen. He is involved with crooked law enforcement officials — most notably in the FBI — as well as the criminal elements in Harlan County that serve his organization's purposes. He is amused by violence and acts with great arrogance when forced to unite with, say, the Crowders of the world. Ultimately out only for himself, Nicky has his eyes on taking Theo Tonin's place one day, and is contemptuous of his boss' son, Sammy.
- Arson, Murder, and Admiration: After Ava splashes him with whiskey and threatens to set him on fire, he turns to Johnny and says "Well, I can see what you like about her."
- The Bad Guy Wins: He's only a moral victor, but still. He robs Raylan of an opportunity to "justifiably" kill him, forcing him to commit what is essentially a crime to take him out.
- Bald of Evil: Very bald, and very evil.
- Blasphemous Boast: In "Decoy", he likens obedience to Theo Tonin to Abraham's unquestioning obedience to God in the Bible.Augustine: See, a lot of people are troubled by the fact that God asked Abraham to do such a thing. But truth be told, God of the old testament... kind of a dick. To me, the real question is Abraham. You know, why would he be willing to entertain the idea of killing his son?Boyd Well, conventional wisdom is he was demonstrating his own faith.Augustine: I think that's wrong. I think Abraham thought about killing his own son and was willing to kill his own son because God told him to do it. God. And when the most powerful being in the universe tells you to do something... You do it.
- The Bully: He taunts Ava at length after Boyd and Picker go after Drew. He's shown to have the maturity level of a middle school bully.
- Character Death: Executed on the airport tarmac by Sammy Tonin and Mr. Picker, who don't want him taking control of Detroit.
- Childhood Friends: With Barkley.
- Cold-Blooded Torture: Has Yolo torture Boyd and Constable Bob.
- Deadpan Snarker: Augustine has some great lines, even when all the other characters are just as snarky."I'm going to need Google Translate on my phone if I'm going to keep talking to you."
- Dragon Ascendant: He'd like to be one, since he doesn't accept Sammy Tonin as the new boss after Theo goes into hiding, but it's cut short by Sammy himself.
- Dragon-in-Chief: Augustine is acting on Theo's orders, but he's the one who coordinates the search for Drew and, after coming down to Harlan, takes over as the main threat to Raylan and Boyd. By the end of the season, his decision to go after Raylan's family, and attempted coup against Sammy, mean that it is he, rather than Theo, who has to be disposed of in order for Harlan to be left in peace.
- Faux Affably Evil: He's witty and quick with a big smile, but displays his true colours as a sadistic bully in a second.
- Food Slap: Ava throws a glass of brandy in his face and threatens to set it alight after he repeatedly insults her.
- Hate Sink: His purpose is to draw hatred away from more likeable villains like Boyd Crowder and Wynn Duffy. He's no more evil than they are, but he is a far bigger jerk, and his lack of loyalty to anyone makes him far easier to loathe.
- The Heavy: Takes over this position after his arrival, displacing Boyd, Wynn Duffy, and the other local villains who had been driving the plot to that point in Season 4.
- Jerkass: Just a jackass, in addition to being evil.
- Lack of Empathy: Augustine simply does not give a damn. He'll kill anyone without flinching.
- Laughably Evil: He's a great deal of fun, due in no small part to the actor's comedic background.
- Mouth of Sauron: Acts as Theo Tonin's mouthpiece in Harlan.
- No Kill Like Overkill: Sammy has his goons shoot up his limo roughly eight billion times.
- Non-Action Big Bad: The only time Nicky ever picks up a weapon is when he executes Barkley, who is seated and in no position to fight back. On all other occasions he has his underlings do the fighting for him.
- Pride: His undoing. He ignored Picker's observations about how ridiculous the Drew Thompson situation was, and conspired to kill Sammy Tonin. The former causes significant problems for the Detroit mob, and the latter drives Sammy to have him killed.
- Psychopathic Manchild: It's not as extreme as say, Coover or Dickie Bennett, and he can fake stability well, but he still has the maturity level of a school bully, something that really shines through in his conversation with Ava and Johnny.
- The Sociopath: What else do you call someone who casually and ruthlessly executes a childhood friend he'd been joking with seconds prior? Not to mention his total inability to grasp appropriate social behaviour, and his general nastiness and bullying demeanour.
- Smug Snake: As proven by Sammy, he's not as all-powerful as he believes.
- The Starscream: Plans to kill Sammy Tonin to take his place as Theo's heir. It doesn't work out for him.
- Villainous Friendship: Type III with Barkley. Barkley considers Nicky a friend and goes out of his way to protect him, but Nicky doesn't think twice about killing Barkley for failing Theo.
- You Have Failed Me: He does this to Barkley.
One of Nicky Augustine's most capable henchmen, Mr. Picker will do anything to improve his position, and survive the various power struggles within the Detroit Mob, switching allegiances without qualm. Following the collapse of the Tonins' empire in Season 5, he is working with Boyd Crowder and Wynn Duffy to set up relations with Mexico.
- Ascended Extra: Not as extreme as some examples, but he went from just another of Augustine's gunmen to a major player in Season 5.
- Bald of Evil: Balding of evil anyway.
- Bodyguard Betrayal: As soon as he realizes that Sammy Tonin got the drop on Nicky Augustine, he switches sides and helps Sammy kill Nicky. He later does it again, this time to Sammy.
- Character Death: Killed by Boyd in "The Toll." Boyd tosses an innocuous pack of cigarettes at Picker, who catches them with a quip. Then it explodes, basically destroying his chest and just leaving him as a body without a torso.
- Chronic Backstabbing Disorder: Has betrayed Nicky to Sammy and Sammy to the Canadians, then turns on Boyd when things go south.
- Deadpan Snarker: Especially when dealing with any kind of law enforcement.
- The Dragon: To Nicky and then Sammy.
- Dragon Ascendant: He's running the remnants of the mob after Sammy dies.
- Even Evil Has Loved Ones: According to Marcos, he has a family, and he seems quite worried when Marcos threatens them.Marcos: [in Greek] What you did can erase everything. Your whole family. Everything, or just you.
- Faux Affably Evil: He's quite pleasant and chatty with Winona. Except the audience already knows what he really is by this point.
- Friendly Enemy: Not to the extent of Boyd or Wynn Duffy, but he seems to respect both Raylan and Art and appears genuinely saddened to hear that Art was hurt.
- Jerkass Has a Point: In "Weight", he warns Wynn Duffy that Boyd is an incompetent business partner whom he should abandon. He reminds Duffy that Boyd recruited the Crowes, who lost half of their heroin shipment.
- Last-Name Basis: Even some of his colleagues don't know if 'Picker' is a first name, last name, or nickname. In "Shot All To Hell", we learn that his full name is Ethan Picker.
- Ludicrous Gibs: Blown into these by Boyd and a hidden explosive device in a pack of smokes.
- Mistreatment-Induced Betrayal: Nicky was very dismissive of him at a diner, ignoring his advice and being a jerk. This didn't lead directly to the betrayal, but may have been a factor.
- Names to Run Away from Really Fast: We later discover that 'Picker' is a genuine surname, but that doesn't make it sound any less ominous.
- Only Sane Man: He calls out Augustine for making poor decisions during the hunt for Drew Thompson and is smart enough to recognize that Augustine's days are numbered.Mr. Picker: (to Nicky) So, out of nowhere, Crowder calls and says he's bringing the marshal, and you just drop everything to play "high noon". You want to explain to me how this makes any sense?
- Pet the Dog: He seems to mean it when he offers Raylan condolences after he finds out about Art's hospitalization. Given that Art saved his life, this makes sense.
- Pragmatic Villainy: He lets Raylan and Bob live because he no longer had anything to gain from murdering two law enforcement officials. Similarly, he opposes going after Raylan's family not because of any moral qualms but because it will get them nothing and it is against Sammy Tonin's orders.
- Punch-Clock Villain: He's pretty chill to Raylan and mentions how he prefers not to be in the spotlight. He also cares little about Augustine and casually abandons him in favor of Sammy when he asserts his leadership.
- Sedgwick Speech: "This shit 'ill kill you." Those were the words he used to described cigarettes, right before the explosive-laced pack Boyd threw him turned his torso into salsa.
- Smug Snake: A less obvious example than Augustine, but he massively overestimates his pull with Wynn Duffy and underestimates Boyd.
- The Starscream: In fact, he's a Starscream TO a Starscream (Nicky Augustine). In Season 5, he murders Sammy Tonin and takes the reigns of the Detroit Mob; not that there's much left of the mob by that point.
- Took a Level in Jerkass: He's much less Affably Evil in Season 5. It makes sense, considering how badly things start going for him.
Theo Tonin's personal bodyguard and most trusted enforcer, Elias Marcos is distinguished by his Undying Loyalty to his boss, and his willingness to kill anybody in the name of fullfilling his orders. Having accompanied Theo to Tunisia, he returns to the USA, and travels to Harlan County, intent on punishing Mr. Picker for his betrayal. This brings him into conflict with US Chief Deputy Marshal Art Mullen, and US Deputy Marshal Raylan Givens.
- Awesome, but Impractical: His massive BFG. It's cool and loud, but it's also ungainly and takes a long time to reload. His trouble with it results in his death; ironically he probably stood a better chance with the regular handgun he'd been using up 'til then, since he's shown to be extremely competent with it.
- Badass Longcoat: He has one.
- Best Served Cold: References this in a conversation with Picker, noting that "a thing like this has no expiration date."
- BFG: Marcos is seen wielding one during his gunfight with Raylan and Art. It actually doesn't help him, since it slows him down and takes a long time to reload.
- Character Death: Killed by Raylan during a shootout with he and Art.
- Dark Is Evil: Marcos dresses entirely in black, adding to the threatening figure he cuts.
- The Dragon: He's the only one of Theo's top henchmen to remain loyal following Thompson's capture, Nicky's betrayal, and Sammy's death. He acts as his enforcer, transport, and bodyguard. If what Art and Picker say is true, he's had this position long before Season 5, and may well have outranked the likes of Quarles and Augustine.
- Dragon-in-Chief: By the time of "Shot All To Hell", Theo is in such bad condition that he can barely move. Marcos, accordingly, is the actual threat of the episode, and the climax comes when he faces off with Art and Raylan in a shootout.
- The Dreaded: Everyone's terrified of him and with good reason. Picker tries to put on a brave front, but he's most certainly very scared. Marcos is nobody to trifle with.
- Faux Affably Evil: When he tries to come across as nice, he just winds up being mocking. It's pretty clear he's about one unpleasant conversation away from slashing the throats of everybody in the room.
- Hot-Blooded: Marcos doesn't like backing down, confronting four armed men in the diner and only retreating at the last second.
- Icy Blue Eyes: He has a stare to rival Quarles'.
- Implacable Man: Marcos will not stop until he's either dead or his goal is completed. He makes it abundantly clear that there's nothing that will dissuade him from killing Picker.
- Obviously Evil: With his all black clothes and cold stare, Marcos is certainly making no effort to appear anything other than a villain.
- One-Man Army: Described as such.
- Praetorian Guard: Described as a "one-man praetorian guard".
- Professional Killer: One of his jobs for Theo Tonin.
- Smug Snake: Not to the extent of Nicky Augustine, but Marcos is still self-assured to the point of suicidal.
- Soft-Spoken Sadist: Much like Wynn Duffy, his voice becomes more whispery the more threatening he wants to be.
- Undying Loyalty: To Theo. It's notable that he's basically putting his life on the line for a fallen king who can't give him much in the way of payment, and Marcos himself seems to consider the whole incident of killing Picker to be a matter of principle.
Detroit Mob Employees
Charles 'Charlie' Monroe
A very wealthy Detroit mob accountant who is arrested by the Marshals.
- Beard of Evil: A goatee.
- Domestic Abuse: Monroe actually seems to have a Pet the Dog moment when he's seen canoodling with his 'maid' Gloria. They seem to have some actual affection for each other. This quickly changes when he begins smothering her into unconciousness and reviving her over and over.
- Politically Incorrect Villain: He's sympathetic to the Confederacy, judging by his collection of Confederate memorabilia.
- Rich Jerk: He's a vulgar, cruel man who thinks his wealth should exempt him from the consequences of his criminal actions.
- Smug Snake: Monroe is very confident about his abilities and power, never wasting an opportunity to tell others just how dangerous he is. The truth of his situation is that he's a glorified accountant who isn't worth Wynn Duffy's time.
- Too Dumb to Live: It was a marvelously bad idea to go after Wynn Duffy by himself.
- Why Did You Make Me Hit You?: After he's done repeatedly smothering his girlfriend, he blames her for making him do it by not being forthcoming with information.
One of Theo Tonin's most trusted hitmen. When Quarles goes out of control, Sarno is one of two killers sent to Harlan County to deal with him.
- Affably Evil: Extremely and genuinely polite even when being arrested. But you can sense that he is a ruthless assassin.
- Badass Baritone: Of course, it's Michael goddamn Ironside. He has an incredibly intimidating voice that's off-set quite well with his often gentle tone.
- Bald of Evil: As bald as Michael Ironside.
- Beard of Evil: A goatee.
- Cool Old Guy: A villainous example. Sarno is tough, intelligent, experienced and fun to watch in action.
- Deadpan Snarker: With wonderous frequency.
- Graceful Loser: When he's arrested by Raylan, he reacts with self-deprecating humour and no bitterness.
- Professional Killer: For the Detroit Mob.
- Psycho for Hire: Subverted. He isn't as psychotic as much as ruthlessly efficient.
- Self-Deprecation: He laments getting old as he's arrested.Sarno: You know, there was a day when I would have said nobody could stealth me.Art: Yeah? What happened? Lose your edge or just realize you weren't that good to begin with?Sarno: Maybe a little of both.
A henchman of Detroit crime boss Theo Tonin, sent to Harlan to find the whereabouts of Drew Thompson.
The Man from Detroit
A 'buttonman' sent to Kentucky by Theo Tonin to locate Drew Thompson. Acting on Boyd's information, he executes several of the Clover Hillers, before clashing with the US Marshals.
- Bitch in Sheep's Clothing: Part of his police officer act.
- Brief Accent Imitation: He's from Detroit, but briefly affects a mocking Southern accent when informing Frank Browning that he doesn't know Shelby.
- Character Death: Killed by Raylan.
- The Dreaded: He is known for having "killed more people than malaria".
- Impersonating an Officer: His M.O. in Harlan; it's how he manages to get into people's homes without resistance.
- No Name Given: He never gets a name, despite most characters (especially antagonists) on Justified getting fun and memorable names like Fletcher Nix or Nicky Augustine.
- Professional Killer: One of the many that Theo employs.
One of Nicky Augustine's henchmen, Yolo is a young thug retained to beat information out of anyone who won't cooperate with Augustine's wishes. Cocky and cheerful, he enjoys hurting people, and often brags about how "You Only Live Once".
- The Brute: His fists are the main reason for his employment.
- Catchphrase: Was nicknamed Yolo because of how often he says it.
- Character Death: Knifed to death by Constable Bob.
- Jerkass: Pure undistilled douche.
- Karmic Death: Killed by his torture victim.
- No-Holds-Barred Beatdown: Delivers an absolutely brutal smackdown on Bob.
- Only Known by Their Nickname: He's never addressed as anything other than Yolo (unless you want to count the times that Raylan screwed up and referred to him as first "Yoda" and then "Yoohoo.")
- Pet the Dog: Declares that he likes Bob and gives him a breather between beatings.
- Smug Snake: May actually be more incompetent and more slimy than his boss, which takes some doing.
- Tempting Fate: With a name like Yolo (as in "You Only Live Once") he was just asking for it...
- Torture Technician: He's used by Augustine to beat up Boyd and later Bob.
- Underestimating Badassery: Does it to Constable Bob, and pays for it.
- Worthy Opponent: Bob's ability to withstand a severe beating and still make sarcastic suggestions impresses him more than anything. His reaction can best be summed up as, "I'm not even mad. That's amazing."
One of Nicky Augustine's henchmen. He's apparently the best sharpshooter in the group, and accompanies Colt during his ambush of US Deputy Marshal Tim Gutterson's convoy.
- Asshole Victim: Colt kills him, presumably on Boyd's orders to give Augustine less of an advantage should the two factions come to blows.
- Character Death: Shot dead by Colt.
- Cold Sniper: He's certainly got the personality, though we never really see his skill demonstrated (the standoff between Colt and Tim never turns to blows). The fact that he was sent along with Colt indicates that Nicky seemed to consider him a good shooter.
- The Quiet One: Barely speaks in his episode of screentime.
One of Nicky Augustine's henchmen, he's sent to take Winona hostage so that Augustine can use her to get to Raylan.
- Beard of Evil: Of nearly Santa-like proportions.
- Character Death: Killed by Raylan and Winona.
- Groin Attack: Shot in the groin by Winona.
- Jerkass: Dominic isn't around for very long, but he's memorable due to how deeply unpleasant he is.
- No Kill Like Overkill: Raylan and Winona shoot him dozens of times.
- Smug Snake: He's utterly confident that he'll get the best of Raylan, and pays for that grossly untrue estimation.
- Would Hurt a Child: He threatens Winona in the most despicable way and presses his gun to her baby bump.
Dixie Mafia Leadership
The widow of Big Country Grady Hale, Katherine Hale is a longtime Dixie Mafia associate, and a friend of Wynn Duffy's who occasionally acts as a consultant for other criminals. She comes out of retirement at the end of Season 5, taking the reigns of the Dixie Mafia and recruiting Wynn and Boyd.
- Beneath the Mask: On the surface, she's warm, sweet, and sexy. Beneath her pleasant exterior is a petty, ruthless woman devoid of warmth.
- Best Served Cold: Katherine believes that Avery Markham is the one who betrayed and ultimately killed her husband, Grady. She's waited decades for him to return to Harlan, whereupon she begins sleeping with him to lull him into a false sense of security while secretly drawing plans to rob him blind and take everything from him. That's downright reptilian.
- Big-Bad Ensemble: Currently duking it out with Boyd Crowder and Avery Markham for Season 6's main villain spot.
- Disc-One Final Boss: Is killed in the third to last episode by Mike.
- Character Death: In "Fugitive Number One", Mikey punches her in the throat to prevent her from killing Duffy.
- Child Hater: In "Sounding", she threatens to lock her grandchildren in a closet when they argue over a video game.
- The Consigliere: To Wynn Duffy, which turns out to be unfortunate for Mr. Picker, who she makes irrelevant, enabling Boyd to get away with blowing his torso to chunky salsa.
- Dissonant Serenity: In "Burned", she's perfectly serene as she shoots Seabass to death. She calmly calls a colleague to retrieve Seabass' dead body while surrounded by blood and viscera.
- Easily Forgiven: Markham allowed her to live even after her stunt with Boyd cost him $10 million.
- Even Evil Has Loved Ones: She's a mother and grandmother. However, she later remarks in private that she gets no enjoyment out of her grandchildren.
- Even Evil Has Standards: Years ago, Avery Markham asked her to run away with him, but she refused because she wanted to support her husband during his trial. Markham admired her loyalty.
- Evil Is Petty: She recruits Ava to help her steal a diamond bracelet. We later learn that she's bitter toward the jeweler because he no longer greets her at the door with champagne, like he did when she was wealthy.
- Faux Affably Evil: She's soft-spoken, pleasant and all smiles, but Vasquez thinks she's worse than her infamous gangster husband, and there's definitely an undercurrent of ruthlessness to her. She also seemingly had Vasquez's boss murdered to disrupt her husband's trial. The more we get to know her, the more she proves herself to be a terrifying and brutal woman without a hint of remorse. Still, it's hard to dislike her based solely on her affable personality.
- Femme Fatale: An older example, sure, but there's definitely something distinctly sexual about her; her slow and sultry way of speaking, the way she ambiguously flirts with Duffy and Boyd...it's easy to see the young woman she used to be. It doesn't hurt that Mary Steenburgen looks incredible at 61.
- First-Name Basis: With Vasquez, though it serves more to demonstrate the depth of their hatred for one another than any kind of friendship. Also with Wynn Duffy, who was a close associate of her dead mobster husband.
- Friendly Enemy: Subverted with David Vasquez, who prosecuted her husband. They initially come off as old friends, and they maintain a glib good humor throughout, but it's almost immediately clear they despise each other. This probably has something to do with the fact that she had his boss murdered.
- Glory Days: Katherine misses the days when Grady, Markham and herself were the Royal family of Harlan. She's bitter that, whereas she was once greeted with fear and respect, many people have forgotten her. She wants the respect and wealth back.
- Grandma, What Massive Hotness You Have!: Being played by Mary Steenburgen, who hasn't aged since 1990, it's inevitable. Duffy, Boyd and Markham are all very aware of her beauty.
- It's Personal: With Vasquez, who put her husband in prison after the two of them conspired to kill his boss.
- Manipulative Bitch: Katherine is a master of manipulation, playing Avery Markham (who is not a man to be played).
- More Deadly Than the Male: According to Vasquez, she was far, far worse than her husband ever was.
- Mutual Kill: With Mike.
- Politically Incorrect Villain: She calls Vasquez a 'beaner'. Vasquez, though is game and gives at least as good as he gets. She also refers to an old friend's sons as 'mongoloids'.
- Pragmatic Villainy: By reputation. Her pragmatism is the reason Duffy brings her on (and shell out $50,000) to assess his partners and decide which he should jettison, i.e. kill. And her reaction to Picker's grisly murder, telling Mike to shut the door so they can clean him up, establishes her as this.
- Punch-Clock Villain: Subverted. She initially seems like a harmless risk assessor, but it turns out she was even more vicious than her husband, whom Vasquez described in court (according to her) as a no-account savage.
- Retired Monster: She was a ruthless gangster who retired to spend time with her grandchildren with no regrets. Now, however, she's out of retirement and she's ready to make the streets run red with blood.
- Talker and Doer: Grady was the face of the Hale criminal empire, while Katherine handled business behind the scenes.
- Widow Woman: Her husband is long dead.
- The Woman Behind The Man: It's initially implied that she, not her late husband, was the real mastermind behind her husband's criminal enterprise. Eventually Katherine confirms that she held the power and was the driving force behind the Hale Empire.
- Your Cheating Heart: While married to Grady, she took Avery Markham (his criminal partner) as her lover.
'Big Country' Grady Hale
Katherine Hale's deceased criminal husband and the former mentor to Wynn Duffy.
- Bad Boss: He had a habit of cutting off his employee's fingers if they failed him or were disloyal. As Markham notes, this kind of attitude did not help him avoid prison or death.
- Domestic Abuse: Katherine implies that he was abusive on occasion. In "The Trash and the Snake", she tells Ava that she loved Grady, but there were "days, weeks, months ...".
- Evil Mentor: To Wynn Duffy, back in the Glory Days of the Dixie Mafia.
- Fingore: According to Katherine, he cut off the fingers of people who were disloyal to him.
- Never Suicide: Grady killed himself in his cell, but Katherine believes that Markham had him killed. After Duffy is revealed to have been the rat, it seems much more likely that Duffy was responsible for Grady's death.
- Posthumous Character: Big Country Grady has been dead for a long time.
- Puppet King: Grady wasn't powerless and he was dangerous in his own right, but it was his wife who was the true power behind the throne.
- Talker and Doer: Grady was the face of the Hale criminal empire, while Katherine handled business behind the scenes.
A loan shark turned real estate mogul, Emmett Arnett is the head of Frankfurt's Dixie Mafia, and a frontman for the Detroit Mob. In an ironic twist, he eventually gets behind in his payments to Detroit, and has to deal with Robert Quarles as a result.
- Big Bad Wannabe: Emmett is a competent criminal but lacks the sheer ruthlessness of both his superiors in the Detroit Mob, and many of his ostensible subordinates in the Dixie Mafia. This results in his being repeatedly upstaged by the likes of Wynn Duffy, and his eventual replacement by Robert Quarles.
- Boom, Headshot!: How Quarles kills him.
- Character Death: Killed by Quarles, who takes over his operation.
- Dangerous Workplace: Shot in his own office.
- Friendly Enemy: To Raylan, with whom he converses easily and (mostly) tells the straight truth.
- A Glass of Chianti: He had a special batch of Kentucky whiskey made for his own consumption and likes to impress visitors by offering them a glass of it.
- Irony: A loan shark who ends up in debt to worse gangsters.
- Loan Shark: Emmitt operates like this from time to time, usually with Wynn Duffy going after the blood in the water.
- Non-Action Big Bad: Emmett is no fighter, which is why he keeps the likes of Wynn Duffy, Billy Mac and Fletcher Nix around.
- Pragmatic Villainy: Arnett is all about the money; he has no time or desire for vendettas and the like. He's actually a pretty forgiving sort, continuing to employ Wynn Duffy even he threatened to use a blowtorch to make Emmitt's body 'as small as I possibly can'. He would be quite a successful legitimate businessman if he hadn't gotten in bed with the Dixie Mafia.
- Reasonable Authority Figure: Subverted. He likes to present himself as a reasonable businessman but when things are not going his way he uses people like Wynn Duffy or Fletcher Nix to do his dirty work for him.
- Sexy Secretary: He has his beautiful secretary, Yvette, pour coffee for guests. The first episode of Season 3 also shows that he's having an affair with her.
- Sharp-Dressed Man: He's always well turned-out.
- You Have Failed Me: An interesting variation. Arnett is way behind on his payments to Frankfort, hence why Quarles kills him. But Quarles himself sabotaged Arnett's attempts to get the money and square things up, so he could take Arnett's place in Harlan and set up his own operation.
Dixie Mafia Employees & Associates
Michael "Mike" Cosmatopolis
Wynn Duffy's quiet, somewhat dim, but very dangerous bodyguard and fellow motor coach dweller. Wherever Wynn goes, Mike is sure to follow.
- Affably Evil: Mike might be a bodyguard for a psychotic criminal, but he's typically a pretty agreeable guy. He isn't sadistic, cruel or boastful and has a code he adheres to.
- Ambiguously Gay: For most of the show, there are no hints as to his sexuality at all—but it has to be mentioned that his Last Request is for Wynn Duffy to hold him in his arms as he dies, which is not something you hear straight men ask for very often. The fact that Duffy himself is of dubious sexual orientation doesn't help matters.
- Ascended Extra: Along with Jere Burns' upgrade to the opening titles, in Season 5 Mike is getting a little more screentime and even some lines. This continues into Season 6. He even gets a character arc!
- Bald of Evil: Shaved bald, but still. He eventually grows his hair out.
- Bodyguard Betrayal: In "Trust", Mikey grows so disgusted with Duffy's CI work that he stuns Duffy, handcuffs him to a table, and calls Katherine Hale.
- Broken Pedestal: When Duffy reveals his past as an informant for the Marshals, Mike is devastated.
- Character Death: Dies after being shot multiple times by Hale, though he manages to kill her beforehand.
- Curb-Stomp Battle: Was on the receiving end of a brutal No-Holds-Barred Beatdown from Daryl Crowe Jr. This says less about Mike's fighting skills (which are formidable) and more about just how big Daryl is—nothing that Mike throws at him will stick.
- Died in Your Arms Tonight: After being shot multiple times by Katherine Hale, he dies in Wynn Duffy's arms.
- Dumb Muscle: Mike may not be particularly intelligent, but he's extremely dangerous.
- The Dragon: For Wynn Duffy. Wynn has had other henchmen who come and go, but Mike is the most loyal and consistent with the most appearances. If you see Jere Burns' name in the opening credits, you're certain to see Jonathan Kowalsky's name follow.
- Dying Moment of Awesome: He goes out saving Duffy from Katherine, fighting her off a good while and managing to kill her even with several bullets in his chest.
- Even Evil Has Loved Ones: Despite the Bodyguard Betrayal and Broken Pedestal, Mike ultimately proves that he does care deeply about Duffy and considers him family.
- Even Evil Has Standards: Mikey values loyalty and swears that he would never betray his "people" in the crime world when he learned that Duffy served as an informant years before.
- Hidden Badass: Mike's ability with a gun remains hidden until Season 5, creating the impression that he's semicompetent at best. Then he drops Charlie Monroe.
- Honor Among Thieves: He's disappointed when he learns that Duffy was the informant who got Grady Hale imprisoned. Mikey strongly believes in loyalty to his "people" in the criminal underworld.
- Made of Iron: Mike takes four bullets at point-blank range which blast right through his body...and he still manages to kill his opponent before expiring.
- Mouth of Sauron: He tries to be for Wynn Duffy. People have to talk to Mike before they talk to Wynn, but usually they just blow right past him.
- Morality Pet: Serves as something of one to Wynn Duffy, whom he appears to actually be friends with. The depth of their friendship is gradually explored, with Mike even telling Duffy that he considers him family.
- Mutual Kill: With Katherine Hale.
- Punch-Clock Villain: He doesn't have much going on outside of being Wynn's bodyguard, in which capacity he only seems occasionally called upon to do bad things, mostly in defense of his boss, thanks to Duffy being a very disciplined criminal.
- Quick Draw: Manages to draw his gun, hit his target, and then drop the gun before Rachel can even get her own gun clear of the holster.
- The Quiet One: Over the course of his two seasons of appearances, he had maybe five lines in total. Come Seasons 4-6, he has many more lines.
- Sharp-Dressed Man: Mike is always well turned out. He wears a suit better than Wynn, in some cases.
- The Worf Effect: On the recieving end of a brutal beating from Daryl Crowe Jr., which serves to remind the audience of just how physically overpowering the huge, but usually non-violent, Daryl can be.
- Ungrateful Bastard: Toyed with. Wynn probably saved Mike's life after the beating Daryl gave him, and forgave him for having told Daryl about the heroin, yet when Mike finds out Wynn was once an informant he immediately betrays him. In the end though, Mike decides that he owes Wynn too much and saves him from Hale.
- Villainous Friendship: As of Season 5, when he gets most of his characterization, he and Wynn Duffy appear to be a Type I. When Duffy's past as an informant comes to light, Mike turns on him, but in the end decides that Wynn matters more than his "code" and dies saving him from Katherine.
- Wicked Cultured: He quite enjoys classical music.
- Wrong Genre Savvy: Mikey's insistence on having a "code" isn't in line with the backstabbing, opportunistic, honourless sociopaths usually employed by the Detroit Mob/Dixie Mafia. It's more in line with an idealistic Western than the world of Justified.
Tanner Dodd is a homegrown Harlan criminal with ties to both the Dixie Mafia and Noble's Holler. He's employed by Wynn Duffy and Robert Quarles to run the Harlan side of their operations, and recruits other local gangsters to help them take over the county's Oxy trade.
- Character Death: Blown up when the bomb squad can't deactivate the mine in time.
- The Dragon: He runs the Harlan side of Quarles's operation.
- Dragon with an Agenda: He attacks Boyd's Oxy clinic even though Quarles has not ordered it and he knows it will start a Mob War.
- Even Bad Men Love Their Mamas: It's probably his only redeeming feature. He is more than willing to sacrifice his own life to make sure that his mother stays unharmed.
- Failed a Spot Check: While invading the home of a weapons salesman.
- Jerkass: Dodd is pretty rude and thuggish even when he's not murdering people in cold blood.
- Land Mine Goes "Click!": And boom goes Tanner.
- Mustache Of Evil: He has a pretty thick 'stache.
- Psycho for Hire: He has no qualms brutally murdering three people as a side job for some quick cash.
- Would Hit a Girl: Blasts Trixie—whom he had been sleeping with in the previous episode—with a shotgun when he finds her at Boyd's Oxy clinic.
Emmitt Arnett's beautiful and seemingly oblivious secretary, with whom he is having an affair.
- The Ditz: Comes across as this in her talk with Raylan, but only as part of her Obfuscating Stupidity.
- Obfuscating Stupidity: When she speaks with Raylan, she comes across as a ditzy secretary who's only slightly suspicious of her boss, Emmitt 'conducts his criminal business in his real estate office' Arnett. This is only a trick; she's actually pretty clued in and even conspires with Quarles.
- Rewarded as a Traitor Deserves: After she gives up her boss and lover Arnett to be killed, she herself is killed by Quarles.
- Sexy Secretary: She's having an affair with her boss. She's giving him a blowjob while he's on the phone to Duffy, prompting the hilarious line, 'Mr Arnett, are you getting a blowjob in your office?'
A washed up former featherweight boxer who works as an enforcer for Wynn Duffy. A racist jackass, he got into boxing and later organized crime because he enjoys hurting people.
- Boom, Headshot!: During the showdown with him, Duffy, Raylan and Emmitt Arnett.
- The Brute: For Wynn Duffy.
- Character Death: Killed by one of Emmitt's bodyguards.
- Death Glare: See that expression he's wearing in the picture? That's his default expression.
- Even Evil Has Standards: While they don't stop him from working for the man or committing his share of heinous crimes, he himself is occasionally shocked by the depths that his boss can sink to, prompting him to matter-of-factly inform Raylan that "Duffy's crazy."
- I Coulda Been a Contender!: He was a professional boxer, but now works as muscle for Wynn Duffy. Raylan calls him a 'never-was'.
- Jerkass: He's an idiot racist and smug asshole without a single redeeming feature.
- Karmic Death: Raylan warned him very sternly not to turn up to the big showdown, and he did anyway. He was killed at it.
- Lightning Bruiser: Billy manages to beat the hell out of a former NFL player much bigger than himself largely by virtue of his speed and quick, successive punches. And a bit of dirty fighting, of course.
- No-Holds-Barred Beatdown: On Gary's extremely likable friend, Toby.
- Politically Incorrect Villain: A racist dumbass who claims to have liked boxing because it meant he got to beat up 'coloured boys'.
- Too Dumb to Live: Billy Mac was warned not to turn up to the big showdown. Billy Mac turned up to the big showdown. Billy Mac should not have turned up to the big showdown.
Fletcher "The Ice Pick" Nix
A psychopathic hitman working for the Emmett Arnett. He forces his victims to play a game with him, wherein they both go for a gun on the table, then stabs them in the hands with an icepick when they go for it.
- Cheaters Never Prosper: Raylan pulls on the tablecloth, bringing the gun to himself, and causing Nix's icepick to miss. Had Nix just gone for the gun it's entirely possible he would have won.
- Creepy Monotone: Nix speaks in a slow, leisurely drawl.
- Evil Counterpart: To Raylan. A gunslinger with a Nice Hat and old-fashioned ideas of settling things.
- The Gunfighter Wannabe: He's a quick draw, but uses an icepick to cheat at his own game.
- The Gunslinger: Nix is an able gunman, which is part of what makes him an Evil Counterpart to Raylan.
- Hoist by His Own Petard: He likes to play a sick game with his victims but Raylan figures out his trick and turns it around on him.
- Knife Nut: His trademark weapon is an icepick and he is even nicknamed "Icepick".
- Lack of Empathy: Nix is an outright sadist without an ounce of compassion for anyone.
- Nice Hat: A darker, smaller version of Raylan's hat to show the Good vs Evil conflict.
- Professional Killer: For the Dixie Mafia and Detroit Mob, and in the employ of Emmitt Arnett when we see him on the show.
- Psycho for Hire: When Raylan asks him that why he didn't run off with the watches and instead came back to kill Raylan, he merely replies "Do I look like I know anything about watches?" Exemplefied in an earlier scene where he kills two men completely unncessarily, given that the police already have his face and MO (he claims he is doing it to protect his ID).
- Sadist: Stoic he may be, but Nix clearly enjoys giving his victims false hope before gunning them down.
- Silent Snarker: Oh, he does speak up, but he can be pretty snarky with just looks and actions. When Quarles asks him to move somewhere else (as in 'not behind him where he has the advantage') Nix moves maybe a foot away, pretty much staying in the same position. Quarles finds this to be Actually Pretty Funny.
- The Sociopath: One of the clearest examples on the show. Nix's cold-blooded demeanour, impulsivity, sadism, and need to look badass are pretty obvious signs of sociopathy.
- The Stoic: His bored, laconic demeanour never changes.
- Villain Ball: Instead of wearing a mask, which he doesn't like to as he's "too pretty", he forces him to play a rigged dueling game and kills the pizza guy he sent to ref the game. Worse still his MO is known by the police, making both murders entirely pointless. When Nix is prevented from meeting up with Arnett, Nix kidnaps protagonist Raylan Givens' ex-wife Winona, and makes Raylan play his game, despite that fact that he has reason to go after Raylan but he has heard of Raylan's reputation and can't resist testing himself against him, rather than flee with the several hundred thousand dollars worth of watches he now has on his person.
A pawn shop owner and drug dealer working for Wynn Duffy. He employs oxycontin addicts like Wade Messer, who he keeps in line through intimidation and drugs.
- Bad Boss: He's perfectly willing to kill, abuse, bully, belittle or otherwise sell out his employees in a heartbeat.
- Bald of Evil: Fogle is as bald as they come and one of the most evil criminals featured on the show.
- Beard of Evil: He seems to make up for his lack of head-hair with a goatee.
- The Bully: Fogle gets his pleasure from abusing his employees, ranging from verbal abuse to threats to sadistic games.
- Character Death: Fogle is killed by an employee he was trying to sell out.
- Cool Car: He has one and chats with Raylan about it.Raylan: Nice car.Fogle: Yeah, I used to own one of them European sports cars. On a weekly basis, somebody would be calling me a douche bag or faggot or some derogatory shit, but now people, they just see it, and they say, "Nice car".
- Deadpan Snarker: Especially with regards to his employees, but he also trades barbs with Raylan.
- Fat Bastard: The big son of a bitch makes his drug-addicted henchmen play "Harlan Roulette".
- Jerkass: Aside from being a sadistic bully, he's rude to his customers.
- Karmic Death: Fogle is killed by his own much-abused henchman.
- Mutual Kill: With Wally, his henchman. They exchange gunfire, killing them both.
- Nice Job Fixing It, Villain!: Raylan wasn't after Fogle in the first place, he was looking for Wade Messer. But Fogle acts suspicious and uncooperative, gaining Raylan's attention.Fogle: Afraid without a warrant, this is friendly as I get.Raylan: Funny, 'cause I came here 'cause I'm looking for my buddy Wade, but the way you're acting...makes me think maybe the person I'm actually looking for is you.
- Sadist: Much like Fletcher Nix, Fogle likes to abuse his employees with a sadistic gun game. While putting one of his henchmen through a game of "Harlan Roulette", he can barely restrain his glee and laughter.
- Tempting Fate: Fogle just can't help but taunt his (armed) henchman over the cushy deal he'll get for giving up Wynn Duffy. It goes pretty much as you would expect.