Beware of spoilers! Only major spoilers and spoilers relating to the current season (6) are whited out!
Bennett Family & Associates
One of Harlan County's oldest crime families, the Bennett's have been in business since Prohibition, selling moonshine and marijuana. They dominate the town of Bennett, and their hand can be felt, not only throughout the rest of Harlan, but much of the south, with their marijuana fields reaching all the way to West Virginia. They have a longstanding feud with the Givens family, which dates back to their days as alcohol smugglers, and which still flares up from time to time.
- Archenemy: The Bennetts are the collective archenemies of the Givens'. On a personal level, Dickie would like to be Raylan's, though he's overshadowed in this regard by Boyd Crowder.
- Bandit Clan: A rural gang of moonshine runners and marijuana dealers, they've since branched out into other criminal enterprises.
- The Clan: They were one, back during the days of Prohibition. Nowadays they are down to just the one nuclear family, though they still operate along these lines, and maintain control over the town that bears their name.
- Corruption of a Minor: They employ 14-year-old Loretta to sell weed.
- David vs. Goliath: The Bennetts, with their greater manpower and established reputation are the Goliath to Boyd's David. Unfortunately for them, Boyd's men make up for their lack of numbers with better training and planning.
- The Dreaded: Within the town of Bennett. When Raylan and Rachel arrive in town hoping to arrest Jimmy Earl Dean—a child molestor—they receive no help from the locals because Dean works for the Bennetts. People would rather have their children at risk from a predator, than chance a confrontation with Mags or a visit from Dickie and Coover.
- Even Evil Has Loved Ones: The Bennetts are a dysfunctional family, but a family nonetheless. Dickie, Coover, and Doyle all look out for one another and their mother, and while Mags is often disappointed by and abusive towards her boys, she still loves them just the same.
- The Family That Slays Together: Let's see...Mags is a marijuana kingpin who poisoned Walt McCready and goes to war with Boyd Crowder. Doyle's her right-hand man and enforcer, who murders two people to cover up his brothers' crimes. Dickie's a spectacular example of arrested emotional development, who ratchets up the highest bodycount of any of them—including Raylan's aunt. Coover's a brutal thug who beats Raylan to a pulp and tries to murder a fourteen year old girl. And surrogate daughter Loretta is a weed-dealer who is now working her way up to taking Mags' place.
- Feuding Families: With the Givens. The entire thing was based on a misunderstanding (a Bennett thought a Givens had sold him out to the police), but no one cares about that any more, and there are very few Bennetts or Givens' left in Harlan County.
- Five-Man Band:
- Hillbilly Moonshiner: They got their start this way, even though the family business is now marijuana. Mags still brews up the occasional batch.
- I Own This Town: Bennett township is the property of the family it's named for, with Mags and her boys brooking no outside interference in how they conduct their internal affairs. Dickie takes the attitude one step further, hoping to one day own all of Harlan County, though he's woefully ill-suited to the task of making this dream come true.
- Mob War: Dickie and Coover almost start one with the Dixie Mafia, and Dickie subsequently embroils the family in a conflict with Boyd Crowder's new gang.
Maggie "Mags" Bennett is the matriarch of the Bennett family, whose history of criminal undertakings includes a large marijuana operation. She's also the mother of Doyle, Dickie, and Coover Bennett, all of whom are disappointments to her in one way or another. With her plans of being a simple wife and mother ruined by her husbands early death, Mags took control of the family's drug enterprise, running the convenience store that acts as their front, and ruling the town of Bennett with an iron fist behind the scenes. She's as famous for her "applie-pie" moonshine as she is for her ruthlessness, and has complex dealings with both Boyd Crowder and US Deputy Marshal Raylan Givens.
- Abusive Mom: She breaks Coover's hand, and it certainly isn't the first time she's inflicted physical abuse upon her sons. She later tells Dickie that if Coover had hurt Loretta she'd have killed him herself.
- Affably Evil: Very, very affable. She's witty, cool and friendly to just about everyone. She often seems irritated when she 'has' to use violence and takes a definite shine to Loretta. She even tries to keep the peace after Raylan kills Coover by having a civilised sit-down with Helen, during which she admits her own culpability in what happened.
- Alas, Poor Villain: By the time that Mags commits suicide there's not much left of the Bennett township tyrant. Her dealings with Black Pike have turned the town against her, and she made the deal in the first place to provide for favored son Doyle, who is now dead. Coover is dead as well, Dickie is headed for prison and Mags' beloved surrogate daughter Loretta views her with nothing but vicious hatred for killing her father. Her criminal empire is also in tatters following a war with Boyd, truly leaving her with nothing. Mags decides that there's nothing left for her, and takes her own life.
- An Offer You Can't Refuse: If you do not want to sell your land to her, she will send her sons over to convince you otherwise. They might use bear traps or wild animals to do the convincing.
- Beware the Nice Ones: Mags is a lot more sociable and easy going than her sons, or other major villains like Wynn Duffy, Robert Quarles, or Nicky Augustine. She is not, however, any less dangerous.
- Big Bad: Of Season 2. It's her attempts, first to extract herself from her family's criminal dealings, and then to win the Mob War that Dickie triggered, that drive the seasonal arcs.
- Book-Ends: In the first and last episode of Season 2, Mags shares a jar of her " apple pie" (i.e. moonshine) with someone, and says almost exactly the same words, revealing that while the apple pie wasn't poisoned, one of the glasses was. In the first episode, the poisoned person was Loretta's dad, in the last episode it was Mags herself.
- Character Death: She commits suicide at the end of Season 2.
- The Chessmaster: Mags stays a step ahead of everyone until the season finale.
- Corrupt Hick: A female variant; Mags dominates the Harlan County marijuana trade, and is the uncrowned Feudal Overlord of the town of Bennett in particular, which she rules through a combination of tradition, the people's fear of Dickie and Coover, and Doyle's position as chief of police.
- The Don: "The Dona" technically, but as the reigning head of one of Harlan's oldest criminal families, Mags otherwise fulfills all the requirements of the trope.
- Driven to Suicide: With her only halfway competent son dead, her criminal empire dismantled and her surrogate daughter longing to see her dead, Mags decides she's had enough. She drinks some of her own poisoned 'apple pie' and expires.
- Even Evil Has Loved Ones: She does love her sons in a twisted, conditional way, and wants to get her grandchildren out of the family business. She also loves Loretta, who she sees as a daughter.
- Even Evil Has Standards: Mags tells Raylan that she stays away from methamphetamines and pills like Oxy due to moral objections. It's unclear if she's being honest, or if she's just savvy enough that she knows the Oxy business invites out-of-town invaders like Quarles.
- Evil Counterpart: Mags has a lot in common with Helen Givens, and their similarities come to the fore when they meet to discuss the family feud. Both of them have experienced hardship as women in the largely patriarchal world of Harlan with their feet firmly planted in the criminal element.
- Evil Matriarch: Of the Bennett clan.
- Evil Mentor: To her sons Doyle, Dickie, Coover, as well as her surrogate daughter Loretta.
- Evil Old Folks: She's in her later years, but hasn't lost her bite.
- Friendly Enemy: Typically presents this front when dealing with Raylan. They know they're on opposite sides of the law, and the family feud can't be forgotten, but they're always civil to each other, and at least early on, come off as genuinely friendly. Towards the end of the season, the facade crumbles, and the feud resurfaces with full force, though the conversation she has with Raylan just before her suicide indicates that she would like to forgive him and move on.
- The Heavy: For most of Season 2.
- Hypocrite: She gives a Rousing Speech against making deals with Black Pike, only to turn around and make a damn good deal with them herself.
- Iron Lady: Under Mags' folksy demeanour is a titanium spine, which emerges whenever she's in the midst of a business deal.
- Laser-Guided Karma: She chooses to commit suicide the same way she killed Walt MacCready. For bonus karma, part of the reason she killed Walt was because she believed she could do a better job raising Loretta than him wrapped up in his sorrow. She kills herself partially out of sorrow that Loretta now hates her.
- Manipulative Bastard: At first she appears to be a simple shop-owner (admittedly, one with a prosperous marijuana sideline). As the story goes on, it becomes increasingly clear that this is very much not the case. Mags expertly manipulates both Black Pike and the people of Harlan County with one speech.
- Mama Bear: She may abuse her sons herself, but she will not tolerate anybody else hurting them.
- Morality Pet: Loretta. It's subverted eventually.
- Never Mess with Granny: She's grandmother to Doyle's kids, and holds an iron grip over her territory.
- Non-Action Big Bad: Mags was never a fighter, and is too old and out of shape to threaten anybody directly. Luckily, she has her boys for that.
- Out-Gambitted: Outgambits Black Pike by coming to a separate arrangement with Boyd behind their representative's back. She herself is outgambitted by Boyd when she sends a small army to attack his allies during a supposed truce, only to discover that Boyd has brought in his own reinforcements and equipped them with much better weapons.
- Parental Favoritism: Favors Doyle and his sons over Dickie and Coover, and Coover over Dickie. And if Loretta is counted as a surrogate daughter, she favors her over all of them.
- Politically Incorrect Villain: Implied by her curt treatment of Rachel.
- Pragmatic Villainy: Mags understands that war is bad for business, and that there's nothing to be gained through bloodshed.
- Retired Monster: Invoked and averted. Mags wants to get out of the marijuana business and retire to the countryside with her grandchildren, despite having no real regrets about her many criminal actions. In the end, Coover's death and Dickie's screw-ups, combined with the renewed Givens/Bennett feud convince her that she was kidding herself, and she takes the family's reins once again.
- Rousing Speech: Gives one at a town hall in order to turn the people of Harlan against Black Pike Mining.
- Smarter Than You Look: At first glance she's a kooky, fun, redneck grandma. She's actually incredibly intelligent and perceptive.
- Southern-Fried Genius: Much like Boyd and Bo Crowder, Mags comes off as an uneducated rube, but actually possesses a very high IQ.
- Tampering with Food and Drink: Her use of poisoned "apple pie" moonshine to murder Walt.
- Underestimating Badassery: Black Pike does it to Mags, and she herself admits to doing it to Boyd Crowder.
- Villainous Legacy: The money that Mags left with Limehouse and the fallout from her deal with Black Pike continues to drive events in Harlan County for a long time afterwards.
Doyle Bennett is the oldest son of crime family matriarch Mags Bennett and, like his younger brothers, something of a disappointment to mom. Still, of the Bennett brothers, he is the most put together, serving as the crooked chief of police. He believes his position gives him more power than it really does, resulting in a brash persona that doesn't sit well with his law enforcement colleagues, especially U.S. Deputy Marshal Raylan Givens.
- Avenging the Villain: Wants to avenge Dickie's crippling and Coover's death.
- Beard of Evil: He has a thick beard and is very evil.
- Bitch in Sheep's Clothing: Unlike Dickie and Coover, Doyle can actually fake being a Nice Guy. It's entirely a facade, though.
- Boom, Headshot!: Tim kills him with one.
- Character Death: Killed by sniper fire while trying to shoot Raylan.
- Corrupt Hick: Doyle's the one who makes sure his mother's rule over the town of Bennett is enforced.
- Deadpan Snarker: Doyle's got a very sarcastic sense of humour, though not to the extent of the likes of Tim Gutterson or his brother Dickie.
- Dirty Cop: Doyle is blatantly corrupt, working for his mother.
- Disappeared Dad: Like the other Bennett boys.
- The Dutiful Son: Follows Mags' every order.
- The Dragon: To his mother, acting as her primary agent and enforcer.
- Even Bad Men Love Their Mamas: Doyle cares about his mom a lot and is very loyal to her.
- Even Evil Has Loved Ones: He loves his mother, his sons, and his wife, and for all his issues with Dickie and Coover, wants payback for what Raylan did to them.
- Even Evil Has Standards: Implied. Following Helen's murder, Arlo works out that Dickie was the culprit because "Doyle wouldn't do this." This could also mean that Doyle is smart enough not to be involved, but given his general lack of dog kicking the possibility that he has standards can't be ignored.
- Faux Affably Evil: Doyle is pretty friendly even when he's reaching for his gun.
- Famous Last Words: His image caption.
- Happily Married: Implied.
- Hidden Depths: He may be a vile snake, but he has a family and plays guitar pretty damn well.
- Killer Cop: Murders two of Dickie and Coover's goons in order to cover up his brothers' crimes.
- Pre-Mortem One-Liner: Tries to deliver one to Raylan, but they end up being his own Famous Last Words courtesy of Tim's sniper shot.
- The Sheriff: Bennett Chief of Police if you want to be technical about it, but the result is the same.
- Smug Snake: Doyle is comfortable in the position he's in and happy about it, but he's a pawn of his mother and isn't much of a planner himself. So he can smirk all he wants as Mags gives him the family fortune, but he earned it only because his competition was so poor.
- "Well Done, Son!" Guy: Averted. His unquestioning loyalty and common sense make him the favorite of the Bennett brothers.
- Yes-Man: He's one to his mom.
Dickie Bennett is the second son of matriarch Mags Bennett, and brother of Coover Bennett and Doyle Bennett. The longtime feud between the Bennett and Givens clans has extra special resonance to Dickie, who was also a high-school baseball rival of now U.S. Deputy Marshal Raylan Givens. It was during one notorious game that Givens provided Dickie with his persistent limp. High-strung and always seemingly scattered, Dickie is a source of disappointment to his mother, with a penchant for concocting schemes that go nowhere but bad. His best perceivable skills are his ability to deal pot and shift the blame.
- Ain't Too Proud to Beg: When Raylan takes him into the woods to kill him, Dickie begs and cries and pleads with tears in his eyes. It's so pathetic and horrible that Raylan actually doesn't kill him.
- Ambition Is Evil: Dickie is the most personally ambitious of the Bennetts, and hopes to one day rule as crime lord of all Harlan County, as Bo Crowder did in his heyday. These dreams do not mesh well with Mags' plan to extract the family's future generations from crime, or with Dickie's own limited abilities, and wind up getting a lot of people needlessly killed.
- Avenging the Villain: Wants payback for Coover's death.
- Bad Boss: When his new minions decide to abandon him, Dickie waits until their backs are turned and then kills them both. He also plans to have Jed take the fall for Helen's murder, and then be killed resisting arrest, and later abandons several of his other henchmen when the attack on Boyd goes south.
- Batter Up!: Tries to beat Raylan to death with a baseball bat. This is meant to be ironic payback for Raylan breaking his knee with a bat in highschool, leaving him with his trademark limp.
- Big Bad Wannabe: Wants to ascend to his mother's position, but is outclassed by Raylan and Boyd both. He's still violent enough and underhanded enough to be a real problem, though.
- Big "NO!": When Doyle is killed in front of him.
- Boisterous Weakling: Dickie talks a lot of trash for a scrawny, physically impaired coward. The fact that he normally has Coover or Doyle backing him up helps explain this.
- Brains and Brawn: As the mildly more intelligent of the two, he plays the brains to Coover's brawn.
- Cloud Cuckoolander: Prison has undermined Dickie's mental health. By Seasons 5 and 6, he's decidedly eccentric, displaying strange gestures, figures of speech, and syntax while talking to Raylan and Tim.
- The Dark Chick: He's definitely the odd one out in the family, lacking Coover's muscle, Doyle's loyalty, and his mother's brains, and is instead distinguished by his scattered thinking and sullen sarcasm.
- Deadpan Snarker: Constantly sarcastic and sullen.
- Dirty Coward: When things don't go Dickie's way he runs or cries.
- Disappeared Dad: Like the other Bennett boys.
- '80s Hair: In Season 3, his hair goes from being a dishevelled mess to an outrageous mohawk.
- Enemy Eats Your Lunch: Parodied. Looking to build his reputation after being cut off by his mother, Dickie does this as part of an attempt to intimidate Boyd. As it happens, Boyd and his henchmen were just discussing who they can target to establish themselves as being back in the criminal game. Dickie's pathetic attempts are seen by Boyd as good fortune, and he can't stop laughing when Dickie tries.
- Even Bad Men Love Their Mamas: Desperately wants Mags' respect.
- Even Evil Has Loved Ones: His brothers Coover and Doyle and his mother Mags. He wants Mags' trust and approval, tries to protect Coover from his mother's wrath and from Raylan ("Don't you hurt my brother, Raylan!") and lets out a Big "NO!" when Doyle dies.
- Even Evil Has Standards: He tries to stop Coover from killing Loretta. Although this was to protect Coover from Raylan and his mother more than out of concern for Loretta. He also refuses to let James Earl Dean go after Loretta in the first episode of Season 2.
- Evil Cripple: Best described as physically crippled, emotionally stunted, and dangerously unpredictable—a winning combination if ever there was one. By Season 5 he is in a wheelchair.
- Fat and Skinny: The skinny to Coover's fat.
- Grew a Spine: He's considerably less cowardly after his first escape in Season 3, talking back to Ash (who has kidnapped him and plans to kill him if the plan fails), mocking two men who want to murder him, shrugging off threats from Limehouse and Hot-Rod, and walking into Boyd's bar despite knowing that the latter wants him dead. When Raylan corners him in the penultimate episode, he actually tries to pull a gun on Raylan, instead of begging for mercy. It is implied that prison life, coupled with a series of near-death experiences, and his belief that he's a dead man anyway if he doesn't get the money, are the reasons for this.
- Handicapped Badass: Downplayed. He might be a crippled, skinny idiot, but he still manages to kill Helen, shoot Ava and trap Raylan, even if doing so earns him no respect.
- Hair-Trigger Temper: Though an unreliable one. Sometimes Dickie can keep his temper during highly stressful circumstances; other times he'll explode with very little provocation.
- Hate Sink: Dickie is there to make his mother look more likeable by comparison.
- The Heavy: Tries to take this role from his mother on occasion, and she is regularly forced to act to cover his screw-ups.
- Inadequate Inheritor: Dickie is the heir apparent to the family weed business, but Mags holds him in very low regard, ultimately handing Boyd control of most of the county behind Dickie's back.
- It's All About Me: Dickie thinks he has fortune and respect coming his way without having to actually earn it. He's more concerned with personal gratification and retribution for past slights than he is with the benefit of the Bennett family as a whole.
- Jerkass: Slightly less-so than Coover, but he's still a smug jackass.
- Kick the Dog: Forcing Walt to put his leg in a bear trap springs to mind.
- Laughably Evil: For most of Season 3. Having lost access to the criminal organization that made him threatening in the first place, while retaining all his humerous quirks, this is pretty justifiable.
- Lean and Mean: Almost emaciated.
- Mood-Swinger: Dickie's abrupt mood changes are part of what make him so dangerous.
- Never Going Back to Prison: So much so that he tries to commit Suicide by Cop by drawing a gun on Raylan. Raylan clips him and sends him back to prison.
- Nice Hat: Always wears his baseball hat.
- Not-So-Harmless Villain: Repeatedly. Dickie's a moron, but he's also utterly vicious, and if you turn your back on him, he will bite you.
- Pet the Dog: Fairly consistently. He drags Hobart Curtis off of Carol Johnson, commenting that the two of them will "have to have a talk about polite," dances with his mother at the party, and does his best to stop Coover from killing Loretta, even volunteering to go after them when Raylan shows up.
- Psychopathic Man Child: He tends to behave like a vicious, spoiled teenager. Word of God is that he is mentally and emotionally 'stuck' in the moment in high school when Raylan broke his leg.
- Put on a Bus: To prison, from which he occasionally comes back.
- The Resenter: Towards Raylan, Doyle, and anybody else who has got it better than he does. The problem is, there are wounded cuttlefish that have it better than Dickie.
- Revenge Before Reason: Dickie despises Raylan for all the trouble in his life, and his thirst for revenge leads him to make stupid and impulsive decisions.
- Rival Turned Evil: Back in high school, he was Raylan's baseball rival. Now he's one of Harlan's foremost gangsters, while Raylan is a federal marshal.
- Sanity Slippage: As seen in Season 6, his time in prison has not been good for his mental health. He's crazier, hammier and dumber than ever.
- Smug Snake: Dicke considers himself a criminal mastermind on par with Boyd or his mother, but his family relations are the only reason he's halfway successful. He tries to intimidate others but rarely succeeds, with the likes of Limehouse seeing him as little more than a joke.
- Sole Survivor: Of the Bennett clan.
- The Starscream: He doesn't necessarily want to take control from his mother, but he does want to be right behind her in command, and his attempts at stepping out from under her regularly jeopardize the entire family.
- Stupid Evil: As Raylan spells out in his final appearance, "You were so hot to start a feud with me that had long since ended, you sold your ancestral land to Loretta Mc Cready."
- Suicide by Cop: May have been attempting this when, after swearing that he could not go back to prison, he pulled a gun on Raylan in the penultimate episode of Season 3. Dickie knows what a good shot and Quick Draw Raylan is, and that trying to get the drop on him is signing your own death warrant, so he may well have expected to wind up dead. Raylan clips him in the leg instead.
- Teens Are Monsters: Dickie was a bully in high school, which is how he ended up getting crippled by Raylan.
- Too Dumb to Live: Although from time to time, he has his moments.
- The Unfavorite: His mother favors both Doyle and Coover over him.
- Villains Want Mercy: Dickie begs and cries and whines whenever someone has him on the ropes.
- Villainous Friendship: Aside from the obvious one with his brothers, he's friends with Dewey Crowe.
- "Well Done, Son!" Guy: He desires his mother's love and approval, and his attempts to get it only make her resent him more.
- Would Hit a Girl: Kills Helen and wounds Ava. In Season 3 he shows up at Loretta's house with a gun; it's a good thing Raylan beat him there.
- Wrong Genre Savvy: Minor example, but a lot of Dickie's bad decisions begin to make more sense if you assume that his starting premise is that he's both Raylan's archenemy and the Big Bad of the series.
The youngest son of matriarch Mags Bennett and brother to Dickie and Doyle Bennett, Coover is big, dumb and possesses a terrible temper. All in all, he is the most disappointing of Mags's disappointing sons and—because he is notably lacking in the intelligence department—the least likely to be intimidated by U.S. Deputy Marshal Raylan Givens. Coover always wants his mother's affection, but can never seem to win it.
- Abusive Parents: Coover might have been a violent idiot, but it's easy to see how he grew up the way he did. Mags was cruel to him and her cruelty continues even after his death. She herself laments her parenting style.Mags: You did kill my baby, but I was the one who let him become a nitwit.
- Beard of Evil: He has one that's too thick to be called stubble, but it isn't a beard on par with Dickie or Doyle.
- Berserk Button: Reminding him that he's not his mother's favorite.
- The Berserker: Descends into a foaming rage during fights. When he and Raylan fight in the Bennett store, Mags has to smack him with a shovel and repeatedly snap 'stop it!' to get him to cease his attack, as if he were a wild animal. By the time of their last clash, in the mine, he is completely out of his mind.
- Brains and Brawn: The brawn to the slightly smarter Dickie's brains.
- The Brute: To Dickie and his mother, serving as little more then muscle. He's very tough though, and even manages to beat Raylan down.
- Character Death: Shot by Raylan, he then plunges down a mineshaft.
- Crouching Moron, Hidden Badass: Coover is almost unbelievably stupid, but get him in a fight and he's all but unstoppable, being one of the few villains to lay an absolute beatdown on both Raylan and Boyd.
- Disappeared Dad: Like the other Bennett boys. He's the only one to comment on the unknown Bennett patriarch, claiming he 'never gave him nothin','.
- Disney Villain Death: He's shot by Raylan and then falls into a mineshaft.
- Drugs Are Bad: Smokes weed, snorts cocaine, and has very few braincells left. Coover's a walking advert for why drugs will ruin your life.
- Dumb Muscle: Very stupid, but very tough.
- Establishing Character Moment: When we first see him, he's stoned out of his mind. The second time he's holding a gun and twirling a dead rat by the tail. He then calls Rachel a racial slur and throws the rat at the Marshals' car while waving his gun in their direction. All of this establishes him as stupid and mean.
- Even Bad Men Love Their Mamas: Like Dickie, he's desperate for Mags' love and respect.
- Even Evil Has Loved Ones: His mother and his brothers. He freaks out when he thinks he might have hurt Dickie.
- Fat and Skinny: The fat to Dickie's skinny.
- Fearless Fool: The main reason why he's not afraid to challenge Raylan, is that unlike Doyle and Dickie he doesn't really consider the consequences.
- Good Old Fisticuffs: Is able to overpower Raylan based on nothing but his ability as a brawler. Jed notes that he would "love to hear someone say Coover couldn't fight."
- Green-Eyed Monster: Towards Loretta who gets all the affection from his mom that he has failed to earn.
- Hair-Trigger Temper: Very short tempered.
- Handicapped Badass: Coover spends half the show with his hand in a cast. This doesn't stop him from giving Raylan the beating of his life twice over.
- Idiot Savant: While not terribly bright in other circumstances, Coover is very good at creating new cultivars of marijuana. After his death, Hotrod and Mags both reminisce about how skilled Coover was in raising new strains with specific properties (i.e., raising or lowering levels of THC).
- Imperial Stormtrooper Marksmanship Academy: According to Dickie, Coover "couldn't hit water if he fell out of a boat."
- Jerkass: He's aggressive and always ready to fight.
- Mighty Glacier: Big and slow, but very strong and very tough.
- My God, What Have I Done?: Actually has a moment like this when he knocks Dickie out and is worried he might have killed him.
- No-Holds-Barred Beatdown: Does it to Raylan twice and Boyd once.
- Pet the Dog: Flips out when Ava kills his wildcat. "She killed Charlie!"
- Politically Incorrect Villain: Refers to Rachel as a 'negress'.
- Psychopathic Man Child: Coover's emotionally about eight years old. He's impulsive, selfish, envious, careless and prone to temper tantrums. Many of his actions are very childish, such as when Mags breaks his hand and Coover just keeps telling her he's sorry.
- The Resenter: Of Loretta, who Mags favors over Coover.
- Too Dumb to Live / Obfuscating Stupidity: His decision to keep Loretta's father's watch seems to be an example of the first trope, but he reveals it was actually a ruse to drive a wedge between Mags and Loretta, who he was jealous of.
- The Unfavorite: Views himself this way, but actually stands higher in Mags' affections than Dickie who comments when breaking his hand that "I like Coover".
- Unstoppable Rage: When Coover goes ballistic nothing can stop him. During his last appearance he's all but foaming at the mouth as he goes after Raylan and Loretta.
- "Well Done, Son!" Guy: Towards his mother. He has a mix of love and hatred for his mother, who he claims never gave him anything. However, Coover does love her and desperately wants her approval. It's clear from his expressions that every cruel word cuts right to his heart and tears him up. Even after she breaks his hand, he desperately tries to apologize for his actions and tell her how much he loves her.
- Would Hit a Girl: He tries to kill Loretta.
Loretta McCready is a young teenager taken in by the Bennett family after her father, who was mixed up in Harlan County's drug trade, goes missing. She forms a particular bond with Mags Bennett, who sees Loretta as the daughter she wishes she had. Later, she also forms a bond with U.S. Deputy Marshal Raylan Givens, who recognizes some of himself in Loretta, a resourceful, fiercely independent child forced to grow up far too quickly.
- Antivillain: She's a drug dealer, is willing to both set up her boyfriend and use Raylan against Hot-Rod, and enters into partnership with Boyd. She's still a thoroughly sympathetic character.
- Bastard Understudy: Mags, perpetually disappointed in her own sons, seemed to be grooming Loretta for this role for much of Season 2.
- The Chessmaster: Spends most of Season 6 matching Markham move for move and purchase for purchase.
- Corrupt Corporate Executive: Downplayed. In Season 6 Loretta sets up a shell company, LM Consolidated, through which she funnels her money and makes purchases that she cannot make face to face. Her position as CEO isn't especially relevant, it simply facilitates her other criminal activities.
- Corrupt Hick: As of Season 6, Loretta aims to take Mags' place as the kingpin of the rural Kentucky marijuana trade.
- Daddy's Little Villain: As the daughter of Walter McCready, she's familiar with the ins and outs of the marijuana trade. As of Season 6, she aspires to become a marijuana kingpin like her mentor and mother figure, Mags.
- Expy: Deliberately done in-universe. Loretta is slowly but surely turning into a younger version of Mags Bennett. Season 6 drives this home, with her speech at Markham's party mirroring Mags' speech at the town hall.
- Happily Adopted: Toyed with. The family that takes her in are clearly good people (obnoxious children aside), but Loretta's not happy there, and ends up striking out on her own with all the money Mags left her.
- Little Miss Badass: Loretta is 14-years-old when she first appears, but she has Nerves of Steel and is much smarter than most of the adults in the series. She's perfectly capable of outrunning, outwitting and outgunning grown criminals. This is most clearly seen in her confrontation with Jimmy Earl Dean, who she gives some nasty scars via a barbed wire and fishhook trap.
- Little Miss Snarker: Her age does not impede her snarkiness even remotely.
- Manipulative Bitch: She took some lessons from Mags, it seems; she successfully uses Raylan against to take care of her Hot-Rod problem by playing on who he is, and later turns Markham's audience against him via Rousing Speech.
- Morality Pet: For Mags, who sees the smart capable Loretta as the daughter she always wanted, or possibly the young woman Mags herself had once been.
- Nerves of Steel: It takes a lot to break Loretta; she only really shows fear when her life is in immediate danger, such as from Coover who she knows can't be talked out of anything simply by virtue of his idiocy.
- Opposed Mentors: After her father's disappearance in Season 2, Raylan Givens and Mags Bennett both take an interest in Loretta's future, with Raylan attempting to extract her from the criminal underworld, while Mags leads her further into it. Loretta eventually sides with Raylan once his cold war with the Bennetts turns hot, but as future seasons show, Mags is the one whose influence has ultimately lasted.
- Roaring Rampage of Revenge: When she discovers that Mags murdered her father. Raylan manages to talk her down before she does something that will forever ruin her life.
- Rousing Speech: In "Burned", she turns Markham's party guests against him, convincing them that she would use legalized marijuana to help Harlan's people prosper. In the dress Mags gave her, no less.
- Teen Genius: Loretta is highly intelligent, and successfully outwits dangerous criminals like Hot-Rod Dunham, Avery Markham, and Dickie Bennett. She even manages to buy Dickie's land and house without disclosing her identity, essentially getting it for nothing.
- Teens Are Monsters: Averted. Loretta's a teenage drug-dealer and all-around criminal, yet despite this, remains one of the most moral characters in the setting.
- Trauma Conga Line: Well, hell. Her mother dies prior to the start of the series, then a child molestor attacks and later abducts her, her father is killed by her mother figure and Coover tries to kill her in a pretty brutal way. Loretta ends up pretty much alone, with nobody to rely on beyond Raylan.
- Troubling Unchildlike Behaviour: Exaggerated. Loretta starts out as a weed dealer, graduates to threatening Mags with a gun, and is now trying to take over the whole of Harlan's marijuana trade in partnership with Boyd.
- Villainous Legacy: Receives one from Mags in the form of three million dollars in Bennett weed money. She's currently using it to buy up most of Harlan, and appears to be aiming to take Mags' place as queen of the local marijuana trade.
- Villainous Rescue: In Season 6, she's the one who stops Boon from attempting a Last Breath Bullet on the collapsed Raylan, stepping on his wrist to keep him from aiming.
- Villain Team-Up: Tries to talk Boyd into one in Season 6, going so far as to announce their partnership to the county in an effort at tying him down in town.
- Wise Beyond Their Years: She's probably one of the smartest and most mature characters in the series despite her young age.
- You Killed My Father: The reason she tries to kill Mags.
A longtime associate of the Bennetts, who is 'employed' by a rogue Dickie Bennett.
- Beard of Evil: He has a very thick beard, although it's shaven when he's seen in Season 3.
- The Bus Came Back: Briefly in Season 3.
- The Dragon: Reluctantly, for Dickie.
- Guilt-Ridden Accomplice: To Dickie; he only stays 'employed' by him because he's scared.
- He Knows Too Much: After Dickie kills Helen with Jed present, Doyle pays him a visit to eliminate the only witness to Helen's murder. Luckily for Jed, Raylan turns up at the same time and takes him into custody, saving his life in the process.
- Punch-Clock Villain: Jed is really only trying to provide for his family and rid the Berwind name of a debt owed to the Bennetts.
- Put on a Bus: To prison.
Walter 'Walt' McCready
Loretta's father, still grieving the loss of his wife while dealing weed without the Bennett's permission.
- Butt-Monkey: He's repeatedly bullied and hurt over the course of his appearance.
- Mercy Kill: As he's dying, Mags claims she's doing him a favor in letting him see his wife faster, since he still hasn't moved on after her death.Mags: You'll get to know the mystery, Walt. Get to see your Sally Anne again.
- The Mourning After: Walt is still deep in mourning for the loss of his wife, to the detriment of his daughter. It's partially why Mags decides to kill him, claiming that Loretta doesn't need his sadness constantly affecting her.
- Small Role, Big Impact: He only appears once in Season 2, but has a big impact on the rest of Season 2 regarding the Bennetts and Loretta.
- We Hardly Knew Ye: Mags has him killed in the same episode he's introduced.
James 'Jimmy' Earl Dean
A child molester who works for the Bennett boys, helping to harvest their weed. His attempted assault on Loretta McCready brings the Kentucky State Police and US Marshals Service into Bennett township, kickstarting the events of Season 2.
- Ephebophile: Targets teenage girls.
- Evil Scars: Loretta escapes from him by leading him into her booby traps, one of which is a net of fish hooks that tear up his face rather badly.
- Gunman with Three Names: Or rather, epheophile with three names. It's lampshaded by Raylan.
- Rape Is a Special Kind of Evil: Both Dickie and Mags express disgust at his behaviour.
- "The Reason You Suck" Speech: Loretta gives him a little speech to demonstrate his delusion and her disgust with him.Dean: You're very funny. That's good stuff.Loretta: Is this gonna be your new line? How we got the same sense of humor? What's in your mind? How do you think this is gonna go? You thinking, "maybe we'll fight a little, then it'll turn to wrestling and tickling and laughing, then she'll say, 'ooh, don't touch me there,' and then she won't stop me"? Is that how it runs in your head? You don't even know what to say now, do you? Even me talking about wrestling and tickling and "ooh, don't touch me there," it's like a spell's been cast, and you won't break it. Well, maybe you're just dreaming and you don't wanna wake up. [Loretta slaps Dean hard across the face] Well, wake up!
- Small Role, Big Impact: Walt's death, which kicks off Loretta's entire arc in relation to the Bennetts, is the result of him calling the cops on Dean.
- They Look Just Like Everyone Else!: While most sexual predators portrayed on television tend to be rather obvious (overweight, balding, glasses, maybe a moustache) Dean is a handsome young man with a clean-cut appearance. It just makes him even more disturbing.
- Too Dumb to Live: Firing a gun in a gas station is a bad idea anyway, but trying to do it when you yourself are covered in gasoline? That's just downright silly.Raylan: The key word in firearm is "fire." When the pin hits the cap, makes the charge explode, meaning there's a spark, which should be of some concern to a man soaked in gasoline.Jimmy: That's bullshit. That spark's too far away from the gasoline.Raylan: You didn't finish school, did you, Mr. Dean?
- Two First Names: Discussed. Raylan and Mags both comment on how Jimmy Earl Dean has three first names and therefore should not be trusted.
An associate of the Bennetts.
- The Alcoholic: He's always either drunk or on his way there.
- Dirty Old Man: Hobart tries to fondle Carol Johnson at the Bennett's party.
- Too Dumb to Live: It's unclear what possessed him to confront Mags Bennett so loudly and angrily. That's akin to poking a lion with a stick. Had Mags been in a less-than-merciful mood, Hobart wouldn't have come out of the confrontation alive.
A huge, dumb thug hired by Dickie when he strikes out on his own, Baz is intimidating to look at, but a terrible shot.
- Bald of Evil: He seems more thuggish then pure, true evil but considering he's a criminal without a hair on his head, he still fits.
- Beard of Evil: Possessed of a fairly heavy beard.
- The Brute: Dickie clearly meant for him to play this role in his new gang.
- Character Death: Shot in the back by Dickie when he tries to walk away.
- Dumb Muscle: He doesn't appear to have much in the way of intelligence, which is fine by Dickie.
- Fat Bastard: Baz is a heavy guy and a basic thug.
- Imperial Stormtrooper Marksmanship Academy: Can't hit a target from a few feet away, for which he is roundly mocked.
- In the Back: With a bullet, from Dickie.
- Replacement Goldfish: Dickie briefly tries to make him into one for Coover, but it fails.
- Screw This, I'm Outta Here!: Tries to bail on Dickie once the war with Boyd gets underway.
- Shotguns Are Just Better: Dickie equips him with one to make up for his poor aim.
Another henchman recruited by Dickie when he strikes out on his own.
- Bald of Evil: A bald criminal.
- Character Death: Shot in the back by Dickie when he and Baz try to walk away.
- In the Back: With a bullet, from Dickie.
- Jerkass: His total screentime consists of him mocking Baz, and then trying to run away when things get tough.
- Screw This, I'm Outta Here!: Decides to leave Dickie once things get too serious for his liking.