Unmasking the Dark Side: The Ruthlessness Scale of Yellowstone Characters Revealed

As one of today’s best neo-Westerns, “Yellowstone” may not be a fast-paced cops-and-robbers series like “Justified” or a gunslinging frontier series like it’s spinoff “1883,” but is instead a political and family drama mixed with classic western themes. But unlike other family dramas, “Yellowstone” has bite, with some of the most violent and vicious characters on television. Far more than one dimensional heroes and villains, the series is dotted with complex and layered people, like family patriarch John Dutton and his perpetual nemesis Thomas Rainwater.

With a combination unique skills and special talents, and a capacity for violence mixed with plenty of street smarts, many characters on the series border on the mean side. Heroes and villains alike respond to threats with brutality in the constantly escalating arms race in the Montana mountain valley. Some have survived, some haven’t. From Rip Wheeler to Dan Jenkins, we’ve compiled a list of the nastiest folks on “Yellowstone,” ranked by ruthlessness.

13. Teeter

Teeter, played by actress Jennifer Landon, is a real cowgirl and has proven it time and time again. With a nearly indecipherable Texas accent, Teeter may have put off many of the ranchers when she first arrived, but she quickly won them over with her rough-riding, cow-roping skills. She’s fit right in on the Yellowstone and in the bunkhouse, and may be tougher than many of the men on the ranch.

But we’ve also seen just how ruthless she can be on a few occasions. Never afraid of a fight, she seems to love getting into trouble and may even enjoy drawing some blood. In “Going Back To Cali,” the gang encountered a group of bikers trespassing on the ranch’s land and told them to leave. Things were already tense, but it was Teeter who excitedly started the melee with one of the bikers. When all was said and done, and after Rip and Lloyd showed up to settle the fight, Teeter told them “that was fun.”

She might not be the sharpest tool in the shed, but what she lacks in smarts she more than makes up for with some good ol’ fashion moxie — and a fierce right hook.

12. Dan Jenkins

Not the outwardly, physically tough kind of ruthless, property developer Dan Jenkins isn’t used to the wild western world and the wild woods of the Yellowstone, arriving in the region from the big city. But once in the mountains of Montana, he uses his business acumen to try to steal the ranch from the Duttons. He nearly succeeds with a shrewd tax scheme, but is thwarted by the Dutton’s physical threats — something he wasn’t prepared for starting doing business in Big Sky Country.

Nevertheless, once Jenkins realized how ruthless Montana — and the Duttons — could be, he wasn’t afraid to fight back. He was even willing to play dirty, teaming up with Thomas Rainwater in his attempt to beat John Dutton. Towards the end of his time on the series, Jenkins started learning how to battle the Duttons on their own terms, even hiring private protection and taking lessons on how to wield a sidearm. Unfortunately, he didn’t learn quite fast enough — while he got in his licks, he couldn’t match the viciousness of another pair of Dutton adversaries, Malcolm and Teal Beck. Making himself an enemy of the Becks was a big mistaken, and Jenkins simply wasn’t up to the challenge of facing down a far more ruthless foe.

11. Wade Morrow

We don’t know much about the grizzled old cowboy Wade Morrow, but we do know that he’s one tough S.O.B. with a mean streak. We know that he was once a member of the Yellowstone, as the brand on his chest attests, and that he was exiled from the ranch years before after being accused of theft. Whatever loyalty he may have once felt towards the Duttons had been washed away, because the veteran cattle rustler and his son Clint fell into the employ of stockholder and nearby rancher Roarke Morris. In the service of Morris, Wade and his son would find pleasure in tormenting the Duttons, particularly their ranchers, by pushing the limits of neighborly behavior.

But what started out as unfriendly taunts became nastier and nastier, with the aim of instigating the Duttons into retaliating. The hope was to prompt John to push back and do something criminal that Morris could nail him for in court, but when John wouldn’t play along with the plan, Morrow escalated his tactics. When blossoming lovers Teeter and Colby were out skinny dipping in a river, Morrow and Clint brutally trampled them with their horses. Teeter was seriously injured, with Colby forced to play field medic in an unsettling scene of wilderness survival, proving Morrow to be more dangerous than we first thought. But his ruthlessness would prove short-lived, because when Rip found out what had happened, Morrow was given a swift ride to the train station.

10. Roarke Morris

When your new villain is played by the charismatic and dashing Josh Holloway, you know he’s going to be more than meets the eye. That’s why, when Beth Dutton first met Roarke Morris fly fishing in a river that ran through the Dutton’s land, his claims of being an innocent passerby didn’t hold water for most viewers. A ruthless rancher who also holds heavy stock in Market Equities, he gets joy out of using the firm to torment the Yellowstone. But when his initial corporate schemes fail to deliver the results he wants, Roarke resorts to less reputable and more ruthless measures, hiring bitter rancher Wade Morrow and his son as enforcers and troublemakers.

But Beth always seems to be one step ahead of Morris, and despite adversaries slippery ways, he remains steadfast in his determination. His failed plans only propel him to step up his attack on the Duttons. Unfortunately for Morris, and like many others on this list, he bites off a bit more than he can chew taking on the Yellowstone. Though he’d get his comeuppance for all the wrong reasons, Rip’s deadly attack on him may still have been justified.

9. Willa Hayes

One of the main villains of the third season of “Yellowstone,” Market Equities’ first CEO Willa Hayes is more cunning than the other big business types that had come before her. Arriving in Yellowstone to back her partner Roarke Morris, she’s not happy about Beth Dutton shorting her company’s stock. She wants the Dutton land, and while she claims it’s for the good of the valley and writes off any negative effects of the deal as “economic evolution,” it’s clear that — like any mega corporation — her motives are anything but noble. Hayes uses money and politics to get what she wants, even offering Jamie a deal she knows will either be impossible to the Dutton family to refuse or turn Jamie against his own family.

While she lets machinations play out within the Dutton household, Hayes maneuvers her company’s interests, buying up surrounding lands and securing permits to develop the property. This includes the construction of a ski resort and international airport, much to the Dutton’s dismay and concern for what those will bring to their proverbial shores. Using these deals, Hayes undercuts the Duttons and deftly orchestrates a claim of eminent domain over a large swath of the Dutton ranch. But Hayes made the mistake of attempting a hostile takeover of Schwartz & Meyer, making Beth Dutton her enemy, and found that her fierceness was no match for the Dutton daughter.

8. Caroline Warner

When Will Hayes was ousted as Market Equities’ CEO, incoming CEO Caroline Warner arrived in Yellowstone and proved even more ruthless than her predecessor. Recognizing Beth as a worthy adversary, Warner makes her an offer she can’t refuse: Become President of the Market Equities’ Montana Division and, in return, receive a controlling interest in their subsidiary, Schwartz & Meyers — her old company, and home to the boss who had crossed her. It’s a shrewd and ruthless move, because Warner would now have Beth under her own roof, taking advantage of her unique skills, and eliminating an enemy in the process.

But when Beth goes against her, Caroline not only fires her, but promises — with explicit language — to destroy the ranch and ruin Beth’s life. We’re only just learning how truly ruthless Caroline Warner can be, but with deep pockets and a personal grudge, we suspect she’ll be showing some pretty sharp teeth. Series star John Emmet Tracy, who plays her assistant Ellis, told The Express, “the Duttons have never faced off against anyone as determined and well-equipped as Caroline Warner. [She] works calmly, methodically and dispassionately. She is not only unyielding, but also extremely prepared and uniquely qualified to play the long game.” It sounds like next season she may move up a few places on this list.

7. Thomas Rainwater

Leader of perhaps the Dutton family’s oldest enemies, Thomas Rainwater is the chairman of the Confederated Tribes of Broken Rock. He runs the Broken Rock Indian Reservation that sits next to the Yellowstone-Dutton ranch in the wild woods of Montana. He’s a thorn in the side of John Dutton from the beginning of the series, when he steals cattle from the Yellowstone. His hard-headedness puts him in prison for the crime. Rainwater is shrewd and cunning, a Harvard educated businessman who uses corporate tactics to achieve his goal of protecting his people and seeing that their ancestral lands are returned to them.

To that end, he’s brokered peace with other enemies of the Yellowstone like Dan Jenkins, and then promptly betrayed him. But when bigger enemies surface, he’s not above putting vendettas aside, as he did when he formed an alliance with John to fight back against the Beck brothers. Like John, he’s willing to do whatever it takes, even if it means bending or breaking the law, to protect his people. “When two men want the same thing, they can either share it or fight for it,” Rainwater once said. Sometimes a friend, sometimes an uneasy ally, one thing is for certain: He’s not to be underestimated.

6. Kayce Dutton

Unlike most on this list, Kayce’s ruthlessness stems not from greed or avarice, a love of money, a tendency towards violence, or even for legacy and land … but from a love of family. Highly skilled and highly trained from his years in the military, Kayce uses his killer instincts in protection of those he loves. He’s the only Dutton who loves his family unconditionally, able to forgive those who’ve wronged him — even his once-estranged father. He is the only who maintains a strong connection to the Jamie, the black sheep of the family, and would no doubt kill to protect him as well, despite their differences.

From protecting his wife and son, to protecting the Yellowstone, and fighting for his family’s lives, he’s done it all. Kayce even fought back against the assassins who came after them in the Season 3 finale. Disregarding the police call to stand down, Kayce violently gunned down the would-be killers without regard for surrounding civilians, and took a slug in the side himself. As Livestock Commissioner, he’s shown a mean side, coming down hard on those who’d cross him. But he’s also shown mercy, allowing Walker to live when Rip would have done otherwise. Kayce’s ruthlessness is not entirely lacking compassion, as he only shows it against those who truly deserve it. But with enemies closing in more and more on the Duttons, Kayce’s vicious streak may rear its ugly head again.

5. Garrett Randall

The recently discovered birth father of adopted Dutton son Jamie, Garrett Randall has a complicated and violent past. As a young father, he and his wife were both consumed by drugs, and in a desperate bid to save his son Jamie’s future, he murdered his wife and let John Dutton adopt the young boy. But after discovering the truth of his parentage, Jamie reconnected with Garrett. While the hardened ex-con makes no excuses for his past, he vows to be a better father to Jamie, and rescue him from the troubled life he has found on the Yellowstone … by any means necessary.

Whether that giving his son the confidence to step out from his adopted father’s shadow, or helping him to build his own life off of the Yellowstone Ranch, Garret seems to be doing what any good father would do to make amends for his absence. But it’s later discovered that Randall went much further than offering fatherly counsel, as he hired a vicious gang for a daring assassination attempt on the entire Dutton family. Though they would not succeed, Randall vowed to keep trying, showing just how ruthless his love for his son was.

4. John Dutton

Dutton family leader John Dutton takes a high spot on our list of most ruthless characters — not for any specific violent act, but for his sheer will to do whatever it takes to keep his ranch and hold on to his family’s legacy. He’ll ally himself with enemies, like corporate tycoon Dan Jenkins and even the less than scrupulous Thomas Rainwater, if it means beating a bigger threat like the Beck brothers. He’s never afraid of pushing back when people push first, and rarely hesitates spilling blood, as long as it’s warranted. Unlike many entries on this list, John Dutton operates under a strict moral code and is unwilling to cause collateral damage or bring suffering to those who don’t truly deserve it.

As Livestock Commissioner and community leader — and the Governor’s lover — Dutton is in a unique position to use political and personal leverage to get what he wants. Among the weapons at his disposal are his family: his son is the Attorney General, and his daughter a wealthy financier. And when his enemies send people to his doorstep threaten his family, he’s more than happy to fight fire with fire, and deliver them back to where they came in body bags.

3. Malcolm & Teal Beck

Actor Neal McDonough has experience playing ruthless western villains, having starred as sociopathic mob boss Robert Quarles on “Justified.” In “Yellowstone” Season 2, he joined the cast as a similarly brutal baddie, Malcolm Beck. Along with his brother Teal, played by Terry Serpico, Malcolm terrorized the mountains of Montana. While trying to make peace with the Duttons, and potentially work together to fight off other outside interests, the pair are incensed when John Dutton declines their offer. Now on opposite sides, the Beck brothers’ first attack comes when they poison the fields where the Yellowstone’s cattle graze, killing an entire herd.

Intent on acquiring the Duttons’ land to build his own Big Sky Casino, the Becks increased their pressure on the Yellowstone, with one of the most ruthless and stunning acts on the series. Hiring a gang of violent white supremacists, the Beck Brother’s orchestrated the kidnapping of young Tate Dutton, holding him for ransom and threatening his life. It was a shocking escalation, and a message to both the Duttons and the audience at how dangerous they would be. Through four seasons of “Yellowstone,” Malcolm and Teal Beck remain the most ruthless villains on the series.

2. Rip Wheeler

Arriving on John Dutton’s doorstep as a teen, the young Rip Wheeler had murdered his father for attacking and killing his mother, and showed up covered in his blood. With a violent origin story, it’s no surprise that Rip grew up to be the most ruthless man on “Yellowstone,” with a vicious temper and a seeming lack of morals. He’s beaten people for small transgressions, crushed his best friend’s hand, and callously murdered more than one ranch hand that got on the Duttons’ bad side. He demands unwavering loyalty from his cowboys, and if he doesn’t get it, they might get stabbed in the back. When it comes to the Dutton ranch and the Dutton family, there isn’t much that Rip won’t do.

From intimidation and murder, to burying bodies with no questions asked, Rip is the one man you don’t want to cross on the Yellowstone. He’ll smash heads with a branding iron, gouge eyes out with his thumbs, and dump the bodies over a canyon and never think twice. That’s evidence enough that he rightfully ranks near the top of this list.

1. Beth Dutton

Beth Dutton is top dog when it comes to shrewdness, cunning, and violent ruthlessness. With a ton of smarts and lack of moral fiber, a mix of cleverness and lack of boundaries, Beth has made victims of everyone who crossed her. As a corporate raider, Beth has relished the destruction of other businesses. She used her experience in the stock market to attack Morris and Market Equities by shorting their stocks, which even inspired every hedge fund manager in New York to do the same. Of course, she’s no stranger to violence herself, having gleefully fought back against her assassins, even knowing she couldn’t overpower them.

Beth is more than a ruthless rancher and has shown her cold-blooded nature at work, having fired more than one assistant seemingly out of boredom. Not just vicious, Beth is vengeful, and unafraid of anyone or anything. She’s ruined the lives Willa Hayes and Bob Schwartz at Market Equities, and schemed to get what she needed from Summer Higgins with no concern for the consequences the activist might see. We can’t possibly catalog every one of Beth’s ruthless acts, but if we malign her any more, we too might end up on her hit list.