Markham's Empire & Tigerhawk Securities
A legendary Kentucky gangster who returns from exile with a private army and a large amount of cash from all the weed he grew in Colorado, determined to win back his empire and lost love, Katherine Hale.
- Affably Evil: What's likely a lifetime of smoking his own product has made him extremely laid back, even as he talks about doling out horrific punishments to traitorous employees.
- Badass Baritone: He speaks with Sam Elliott's magnificent deep voice.
- Bad Boss: When giving Katherine advice on dealing with Boyd, he says that he ensures loyalty by overpaying his employees, making sure they're looked after and happy, arguing for the carrot rather than the stick. Then, when pressed, he says that if his employees cross him he'll cut out both their eyes as a "good start". Apparently cutting out one eye is insufficient because a one-eyed man can "still see, still get a driver's license, even". Nor is he in the market for an Honest Advisor.Walker: Permission to speak freely, sir?Markham: You about to give me an opinion, or a warning, or both? Seems to me I've been perfectly clear about what I expect to transpire down here. Shouldn't be any more up for discussion.
- Big Bad Wannabe: Markham is introduced with the same sort of fanfare as Bo Crowder, Mags Bennett, and Robert Quarles, but his schemes ultimately go nowhere, and rather than driving the plot forward, he finds himself the target of schemes from players like Boyd Crowder, Wynn Duffy, and Katherine Hale.
- Boom, Headshot!: How Boyd takes him out in the series finale.
- The Chains of Commanding: Markham gives this trope as his counterargument to Walker not wanting to kill Choo-Choo. He tells Walker being in charge means having to make the hard decisions. He sees Choo-Choo as The Load and gives his own anecdote to Walker's about injured commrades. He thinks they should be abandoned or be given a Mercy Kill for the good of the whole unit rather than risk dragging everyone else down.
- Character Death: Shot in the eye by Boyd.
- Cheshire Cat Grin: He has a very unsettling grin.
- Cool Old Guy: Markham might be evil, but he's undeniably cool. He's first seen lounging in bed with Katherine Hale smoking weed and being generally affable. It helps that he's played by the legendary Sam Elliott.
- The Dreaded: One of the few people in the world who can actually intimidate Boyd Crowder, just from hearing his name.
- Even Evil Has Loved Ones: As ruthless as he might be, Markham does have genuine affection and love for Katherine Hale.
- Even Evil Has Standards: Markham takes offense when Seabass insults Katherine and refuses to let him steal Katherine's engagement ring, even though Seabass is holding them both at gunpoint.
- Every Man Has His Price: Markham believes that everyone can be manipulated with money. He ensures his employees' loyalty by paying them well. Through Walker, he offers landowners handsome sums of money in exchange for their land. When Walker is injured and wanted, Markham pays Seabass not to rescue him. During his conversation with Art, it's implied that he used his considerable wealth to get out of trouble with law at least once. Finally, he woos Katherine by promising to take care of her with his wealth and giving her an enormous diamond engagement ring.
- Even Evil Has Loved Ones: Despite all they put each other through, Markham does seem to be genuinely in love with Katherine Hale. He even parts with his wealth when he believes that Boyd is holding her for ransom. When Raylan informs him of her death, he falls into despair.
- Evil vs. Evil: They might be sleeping together, but Markham is still at odds with Katherine Hale. Neither of these people are on the side of the angels.
- Eye Scream: Boyd kills him with a bullet to the left eye.
- Hypocrite: Markham says he values loyalty, but repeatedly undermines loyalty between his henchmen. When Choo-Choo becomes a liability, he orders Walker to kill Choo-Choo, unmoved by Walker's story about their time together in the military. When Walker is wounded and wanted by law enforcement, Markham pays Seabass not to retrieve him. It seems that Markham values his henchmen's loyalty to him, not to each other. He's also a big believer in using cash as a motivator, when his own motivation is due largely to his love of Katherine Hale.
- Informed Ability: Markham comes with an earthshattering reputation as one of the most dangerous criminals to ever come out of Kentucky. Yet he spends most of the season being manipulated or targeted by one faction or another, quickly loses control over his men, and thus far has failed to accomplish anything.
- I Will Punish Your Friend for Your Failure: In "Fugitive Number One", he threatens to have Earl killed unless Carl executes Boyd.
- Jerkass Has a Point: When Markham and Walker arrive at Ava's house to intimidate her, Markham gives her advice on her criminal career. He reminds Ava that successful women in the crime world need to be twice as ruthless as men and willing to take actions that the men will not. Otherwise, Ava will only be a "token" whom other criminals will target to get at Boyd.
- Kick the Dog: He tells Carl that should he fail, he'll have Boon kill Earl. When Carl himself dies, Markham still wants to kill Earl to fulfil his threat to a dead man, even though it's pointless bloodshed.
- Love Makes You Dumb: He knows exactly what kind of woman Katherine is, but he loves and trusts her anyway. He parts with his fortune in order to ransom her from Boyd, only to learn that Katherine was in on the trick the entire time.
- The Mark: Markham is the target of several schemers who hope to make off with his ten million dollars.
- Nerves of Steel: You're holding a gun on him? Don't expect him to show a hint of fear.
- An Offer You Can't Refuse: If Markham wants your land, he will send one of his mooks with a generous offer to buy the land. If you decline the offer, he will come back with a better offer. If you refuse a second time, your house might burn down or your furnace might have an 'accident' and kill everyone inside the house through monoxide poisoning.
- The Plan: His men are going on his behalf to every landowner in the area, offering ridiculous amounts of money to get the owners to sell to him. Or else. Markham is operating under the belief that Kentucky will legalize marijuana in the very near future, so he wishes to have as much fertile land as possible to grow his product.Though Markham has not yet stated it himself, Wynn, Katherine, and his mooks are all seen discussing this as the main goal. According to Wynn, it's being discussed behind closed doors before announcing the vote to legalize. Wynn believes Markham wishes to have the leg up on every other pot grower in the area before they get word of the vote. Along with Katherine, it's why he came back from his exile in Colorado.
- "The Reason You Suck" Speech: Markham gaves a short but eloquent put-down to both Boyd and Ava, critical of them for playing out a "fantasy" of an outlaw life and letting Boyd know that he's still small-time no matter how big he acts.Markham: Come to reconnoiter my place of business, living some fantasy outlaw life, just you and Boyd against the world.Ava: Sounds like you know a thing or two about it.Markham: I know for a woman to survive in this line of work, she's got to be harder than the men, ready to do the things they won't. I know women who have that in them. My question is, are you that kind of woman, Ava? Because if you ain't, then you'll never be more than a token, something that can be threatened or hurt just to keep your man in line.
- The Stool Pigeon: Katherine Hale and Art separately come to the conclusion that Markham betrayed "Big Country" Hale to the authorities before retreating to Colorado. Subverted. Turns out he never was the snitch. It was Wynn Duffy all along.
- Talking to the Dead: In "Collateral", he's on the verge of tears when he talks to Katherine's corpse at the morgue.
- Villainous Breakdown: The longer he stays in Harlan, the more irritated he becomes with how events spiral out of control. After Loretta gives a devastating speech that turns a crowd of potential buyers against him, he's seen angrily downing a drink with clear panic in his eyes. After Katherine dies and Ava flees with his money, Markham comes unglued. His final scene in "The Promise" shows him threatening Ava with unbridled fury.
- Would Hurt a Child: Seeing Loretta as a threat, Markham makes plans to take her out of the picture without showing any turmoil over the idea of murdering a teenage girl.
- You Have Outlived Your Usefulness: He casually betrays and abandons henchmen the moment they become inconvenient. He ordered Walker to kill Choo-Choo when Choo-Choo because a liability, then paid Seabass not to retrieve an injured and wanted Walker.
- And Your Little Dog, Too!: In "Trust", he orders Boon to murder Loretta's great-aunt.
- Band of Brothers: Played with. They do feel like they owe each other loyalty, but Walker and Seabass betray Choo-Choo, then Seabass betrays Walker. None of them feel good about their betrayals and the Sole Survivor Seabass is guilt-ridden.
- Fish out of Water: Though they are experienced soldiers and excellent in intimidating people on Markham's behalf, as time goes on they are shown to be out of their element when acting as criminals. When an interrogation goes wrong, they decide to dump the body in the woods figuring that no one would ever find it. Turns out they wrapped the body in a carpet and dropped it on a hunting trail. During hunting season. The poor guy's corpse is found within a week. They also didn't strip the body, so the local police not only find his ID but Raylan's business card as well. Guess who they immediately call to help identify the body? To take it a step further, they are all killed around the halfway point of the season, due to bad luck, incompetence, or not knowing to how harden criminals act.
- Mooks: The two mercenaries who accompany Walker when meeting up with Choo-Choo to kill him. They never appeared before, don't have names and are killed only seconds into a sudden gunfight with the Marshals.
- Private Military Contractors: A small group of former Special Forces veterans who fought in Afghanistan.
- Psycho for Hire: All of them, even Choo-Choo, are willing to commit murder on behalf of their employer.
- Terrible Trio: With Walker as the leader. Choo-Choo and Seabass are the ineffectual henchmen.
A special ops veteran who spent most of the last decade deployed in combat zones, as a soldier and later a private contractor. He now uses the legal skills he developed during his military career in his job handling security for a quasi-legal businessman.
- Ax-Crazy: In "The Hunt", an injured and desperate Walker menaces a frat boy who annoys him, then kills two paramedics in cold blood.
- Badass Beard: He's former special ops, and that beard is quite magnificent.
- Band of Brothers: Despite his Stepford Smile and slimy personality once he decides to stop being "nice", he seems to genuinely care for his fellow comrades, especially Choo-Choo. When tasked by Markham to kill Choo-Choo, the former seeing the latter as the weak-link due to his slow nature and loose lips, Walker reminiscences about the accident that maimed Choo-Choo; Walker was riding right behind Choo-Choo's vehicle when it flipped up and crashed on Walker's. Walker comments that he and their unit couldn't believe Choo-Choo survived the accident that killed everyone else. He also tells Markham about the 'real' Choo-Choo, the man before the head injury. He basically defines this trope when pleading with Markham to not order Choo-Choo's death. It doesn't work.
- Beard of Evil: He's an evil, ruthless man with a beard.
- Berserk Button: You don't want to call him a peacock. He'll take it poorly.
- Character Death: Raylan shoots him in the back.
- Disc-One Final Boss: Despite being established as a dangerous cold-blooded former Special Forces operator, Walker and the rest of Tigerhawk Securities are quickly killed off halfway the season. This forces Markham to hire Boon as a replacement.
- Disproportionate Retribution: It's strongly implied that he killed an elderly couple off-screen for refusing to sell him their land and calling him a peacock. He does kill them, but instead of outright murder, he and Seabass cover the couple's windows with plastic sheets so they'll die from carbon monoxide poisoning in an 'accident'.
- The Dragon: To Avery Markham.
- Enemy Mine: After Markham abandons him when he goes on the run, he breaks into Ava's house and holds her hostage so he can form an alliance with Boyd. He planned on sharing the combination to the safe filled with Markham's money and splitting its contents. He's killed by Raylan in the same episode however when Markham betrays him a second time and offers a reward for his capture, dead or alive.
- False Reassurance: After telling a cohort that he'll probably kill someone, he laughs and says he's kidding: he'll definitely kill someone.
- Faux Affably Evil: Walker is polite and smooth-talking, but he carries an air of undeserved superiority and smugness. It's pretty clear that he thinks he's better than everyone else in the room, and as such he's very condescending to the people of Harlan. Not only that, he has a frightening temper and it's clear he's just barely containing his psychotic side. Everyone who he's spoken to, from Raylan to an elderly couple, suss out within seconds that he's not to be trusted even remotely.
- Hidden Depths: Sure, he's a slimy psychopath, but Walker is a big believer in brotherhood and cares for the men under his command. Money isn't his only motivator.
- Hypocrite: He'll kill two ambulance drivers execution style and will kill people on Markham's behalf to get their land, but he calls Raylan out for fatally shooting him in the back. He does this after running from Raylan and simultaneously shooting over his shoulder in Raylan's direction while running towards the woods.
- Nice Job Fixing It, Villain!: Had Walker's outfit left Caprice alone after Calhoun's murder, they could have saved themselves several dead henchmen and a lot of trouble with the law.
- No Sense of Personal Space: He stands uncomfortably close to people when trying to charm or intimidate them. He also has no respect for their personal belongings. He drives onto Raylan's fields instead of using the roads, wipes his nose on an elderly couple's laundry when they refuse to sell him their land, and grabs a woman's groceries when trying to glean information from her.
- Pet the Dog: He desperately tries to defend Choo-Choo to Markham, practically on the verge of tears when ordered to kill him.
- Psycho for Hire: Walker is a terrifying psychotic who masks his evil with a veneer of artificial politeness; he's working for Avery Markham and shows no compunction about carrying out heinous acts for his boss.
- Sesquipedalian Loquaciousness: Clearly a hallmark of his Deadwood days, Walker is eloquent and never uses one word when five will do. Boyd himself notes that Walker likes to talk almost as much as he does.
- Slimeball: As much as he tries to be charming, his manipulative behavior and lack of respect for other people's boundaries mark him as a slimy man.
- Stepford Smiler: Type C. Underneath the phony smile, he's a ruthless criminal with an explosive temper.
- The Un-Reveal: His final words are insisting that he wasn't helping Markham for the money, but he expires before he can explain what that means.
Mundo A.K.A. Choo-Choo
A dim-witted contractor who works alongside Seabass and Ty Walker.
- Accidental Murder: In "Sounding", Choo-Choo and Seabass intimidate Calhoun for information. When Seabass tells Choo-Choo to rough-up Calhoun, Choo-Choo hits Calhoun so hard that he dies instantly.
- The Brute: He's the muscle in the group, but courtesy of his brain injury he's not up for much else.
- Character Death: Raylan and Tim riddle him with bullets. He manages to drive away, stopping on train tracks in an attempt to invoke Death by Irony. However he bleeds out before the train arrives.
- Crime After Crime: Averted and lampshaded. Choo-Choo claims that the only reason that he did not kill Raylan is because they were out in the open and there might have been witnesses. If he killed the witnesses, there might have been witnesses to those murders as well and he would have been forced to kill even more people.
- Death by Irony: Attempted, anyway. After a shootout with the Marshals, he parks on some train tracks and waits for it to hit him. Not only does the train stop before it hits him, he dies from his bullet wounds before it even has the chance.
- The Ditz: Shrapnel struck Choo-Choo in the head during his time in the military, and as a result, he's mentally slow and prone to making bad decisions.
- Dumb Muscle: He's a large, powerfully built man who works for Walker, but he's not terribly bright.
- Dull Surprise: His default facial expression, which carries his dim-witted nature across very well.
- Hidden Depths: Choo-Choo might appear to not have much going on upstairs, but he's a bit more introspective then he lets on. He's still stupid, but he's aware of his own degraded mental faculties and it saddens him that so many consider him to be just a big dumb guy.
- The Load: Markham sees him as this and orders his death.
- Meaningful Name: His name comes from his punches being hard and fast, like a choo-choo train.
- Minion with an F in Evil: Not that he isn't willing to kill, but Choo-Choo is mostly dim and downright helpful on account of his brain injury.
- A Simple Plan / What an Idiot!: Walker instructed him to follow Raylan and Tim in his car. When Raylan confronts him, he allows Raylan to drive off with his car, leaving him stranded. When Tim pulls up later, he fails to recognize Tim's vehicle as the same vehicle he'd been following earlier. Choo-Choo not only accepts a ride from Tim (failing to realize that Tim is a federal marshal), but shares details of Walker's operation with him.
- Wouldn't Hit a Girl: He volunteers to kill Caprice to clean up his own mess, but can't bring himself to do so, although it has more to do with the fact that she's one of the few people who is nice to him. It ultimately leads to his death.
Shawn A.K.A. Seabass
A contractor who works alongside Ty Walker and the dim-witted Choo-Choo.
- Beard of Evil: Not to Walker's level in either bearded magnificence or pure evil, but he's still an unpleasant unshaven fellow.
- Boom, Headshot!: Katherine Hale shoots him in the head, splattering his brains over the wall.
- The Caretaker: Walker unofficially assigned him as a caretaker to Choo-Choo, although he was reluctant to say the least.
- Character Death: Katherine shoots him in the chest and head when he tries to extort her and Avery.
- Cold-Blooded Torture: Torture tactics were part of his military training. He threatens to torture Calhoun for information before Choo-Choo accidentally kills Calhoun with an overpowered punch.
- The Dragon: Seabass gets promoted to The Dragon for Markham with the loss of Walker. It doesn't last long as he's killed an episode after Walker dies.
- Evil Redhead: He's a redheaded Psycho for Hire/Torture Technician.
- Jerkass: Seabass is impatient, lacking Choo-Choo's dimwitted affability or even Walker's creepy Stepford Smiler routine. He establishes himself fairly quickly as a dick.
- Never My Fault: In "Burned", Seabass blames Markham for making him betray Walker, even though Seabass was perfectly willing to take Markham's money at the time.
- Psycho for Hire: Much like Walker, he's a ruthless killer who doesn't bat an eye at killing innocents.
- Sadist: Seabass becomes very creepily nostalgic about a past torture victim.
- To the Pain: He gives a nice little speech about torture to a hapless victim."I remember this one instance, an Afghan, a brother of a Taliban leader, who just wouldn't talk. I mean, this this guy had conviction. You ever heard of a peroneal strike? Hitting the peroneal nerve over and over, day after day, hour after hour? This young fella held out for over a week. Ouch. But he finally talked. All that unnecessary pain. Could have been over before it started. The doctor that treated him said it looked like he was hit by a bus."
- Too Dumb to Live: Holding two dangerous, seasoned crime lords at gunpoint wasn't his smartest move. Katherine tricks him into letting her retrieve her purse, then shoots him to death.
- Torture Technician: This is one of his specialties; he enjoys inflicting pain and he has a natural talent for it.
- What You Are in the Dark: While he places some emphasis on loyalty among his comrades, Markham is able to quickly convince him to abandon Walker with the promise of increased payment. After Walker's death, he feels guilty over his decision which leads to his attempt to extort Markham and Hale.
A deranged and sadistic gun thug employed by Avery Markham in Colorado.
- Abusive Parents: It's implied; Boon was in and out of foster homes throughout his childhood, and describes many of them as being violent."When I was a kid can't tell you how many foster daddies I had, angry pricks, one and all. Lay three hots and a cot with a side of ass whupping. I come to rely solely on my own wherewithal at a tender age, not unlike yourself."
- Ax-Crazy: Boon always seems to be one wrong word away from killing everyone in the room.
- Awesome, but Impractical: His preference for headshots (just in case his target is wearing a Bulletproof Vest ). Ultimately saves Raylan's life; Boon proved Raylan's equal in terms of speed on the draw, and had Boon gone for center of mass, would have achieved a Mutual Kill.
- Blood Knight: The prospect of violence is one of Boon's favorite things. He's incredibly excited by the idea of an Old West style showdown with Raylan; it might be the thing he wants most.
- Boom, Headshot!: Deconstructed. He admits that he has a tendency to go for headshots, which results in his failure to kill Raylan in the end. His shot goes through Raylan's hat and merely grazes his head, whereas Raylan, who teaches cadets to aim for the heart, lands a fatal killshot on Boon.
- Born in the Wrong Century: Behaves and even talks like he's a desperado from the Old West instead of the 21st century.
- Card-Carrying Villain: He refers to himself (in a roundabout way) as a deranged and dangerous individual.
- Character Death: Shot by Raylan in the final episode. He does try to get in a Last Breath Bullet, but Loretta steps on his wrist to keep him from aiming properly and he expires.
- The Dragon: To Avery Markham now that Walker and Seabass are dead.
- Dragon Their Feet: He outlives Markham, but not for long. He ends up becoming the last antagonist in the series that Raylan kills.
- Ephebophile: Strongly implied given his rather horrifying come-ons to the teenage Loretta McCready.
- Evil Scars: Has a thin scar stretching from his bottom lip to his chin. As for the evil, well...look at the other tropes under his name.
- Establishing Character Moment: Boon establishes himself in a very frightening scene; he leaves a dead snake in Loretta's home, bursts through the front door with a big psychotic grin and proceeds to start a Faux Affably Evil conversation with her littered with barely masked threats, boasts of his ability as a sharpshooter and calls himself deranged. All this makes it clear what a crazy, evil son of a bitch Boon is.
- Faux Affably Evil: He's all smiles and compliments, but he isn't even bothering to hide what an outright psychopath he is.
- The Gunslinger: A villainous version. He flourishes his gun a lot, boasts about being a Quick Draw, and is a good enough shot to shoot the head off a snake.
- Hate Sink: He's a vile man, even compared to other criminals in the series.
- Hoist by His Own Petard: He was desperate to face off against Raylan in a Western-style shootout. When he finally did, he came out the loser.
- I Call It "Vera": Boon has named his revolver "Jenny".
- Kick the Dog: When Raylan asks him what will make him any better than the deceased Tigerhawk Securities, he insultingly calls them "jarheads" and states they didn't have souls.
- Last Breath Bullet: Subverted. Despite being fatally wounded, he tries to grab his gun and shoot at the collapsed Raylan again, but Loretta stops him and he dies unable to get off another shot.
- Leitmotif: One of the few characters in the show to have one. It's a low, sinister tune that tends to play when he's menacing someone... which is most of his screentime.
- Nice Hat: After meeting Raylan and becoming obsessed with the idea of having a showdown with him, Boon has a custom-made black hat which even Raylan admits looks cool. Raylan takes it for his own after killing Boon in their last confrontation that left his own hat torn up from a failed headshot.
- Psycho for Hire: It's unclear where Markham found Boon; likely a padded cell somewhere. Markham needed some new muscle after losing the entire Tigerhawk Securities group in only three episodes.
- Revolvers Are Just Better: He has one, in keeping with his gunslinger-style, and is quite proud of it.
- Sadist: If there's one thing Boon loves, it's seeing others in discomfort and pain. Especially if he's the cause of that pain.
- The Sociopath: He murders people without remorse and delights in creating discomfort, fear, and suffering. In "Trust", he admits that his lack of conscience is the reason that Markham hired him.
- Troll: Boon loves fucking with people. He screws with a hipster at a diner for basically no reason other than entertainment and he doesn't like the man's hat.
- Villainous Crush: On Loretta, it seems. He's attracted to her, particularly her spirit, and acts very creepy toward her. When discussing her, he refers to her as "my girl".
- Worthy Opponent: He appears to be building Raylan up as this in his mind. When he first meets him, he's giddy that Raylan is just the cowboy he pictured him as, and seems to look forward to the prospect of going up against him. Raylan's pretty put off by this attitude.