This article’s featured illustration is by Frederic Remington, whose iconic artwork helped define how we picture the Wild West. His dramatic scenes bring the grit and legend of frontier life vividly to the page.
The American West has always called to me, not just because of the wide-open spaces or the promise of adventure, but for the stories. I’ve spent years digging into the tales that shaped our frontier. And if there’s one thing I’ve learned, it’s that the line between hero and outlaw is as thin as prairie grass. And seven figures weren’t just criminals; they were larger-than-life personalities. Folks whose boldness, cunning, and sometimes even charm left a mark on the West, and on American folklore itself.
What ties these outlaws together isn’t just their notoriety. It’s the way they captured the imagination of their time and ours, shaping modern Western folklore and inspiring the movies, books, and legends we still enjoy today. Each one, in their own way, challenged the order of things, lived by their own code, and became legends—sometimes in life, always in death.
Whether they were seen as villains or folk heroes, their stories endure. Stories that remind us that the Wild West was never just black and white. It was a place where grit, wit, and a touch of rebellion could change the course of history. Let’s ride into their stories.
1. Billy the Kid: The Boy Bandit Who Became a Legend
Billy the Kid wasn’t born into infamy. He was born Henry McCarty, a skinny, quick-witted orphan who spent his early years in the slums of New York before drifting west with his mother. Legend paints McCarty as a cold-blooded killer, but the truth is more complicated. His charm, humor, and loyalty made him a figure whose story continues to fascinate, blending fact and myth.
Billy the Kid’s real notoriety began during the Lincoln County War, a bloody feud between rival ranchers and businessmen. He picked sides and quickly became the most hunted man in New Mexico. His escapes from custody are the stuff of legend. Once, he slipped his handcuffs and vanished from a jail cell. Another time, he killed two deputies and walked right out of the courthouse in broad daylight.
Little-known fact:
After his infamous escape from the Lincoln County jail, Billy the Kid left behind a note for his jailer, a fella named James Bell. It simply read, “I’m sorry, but I had to do it.” The note was later lost, but several witnesses swore it existed—just another glimpse into the Kid’s complex character.
Billy the Kid met his end at just 21, shot by Sheriff Pat Garrett in a dark room. But some say Garrett let him go, and that Billy lived out his days under a new name in Texas or Mexico. Whether outlaw or folk hero, Billy the Kid’s legend lives on because he embodied the wild, unpredictable spirit of the West.
2. Jesse James: Robin Hood or Ruthless Robber?
Jesse James is a name that still stirs up debate at any cowboy gathering. Born in Missouri, Jesse grew up in the chaos of the Civil War, riding with Confederate guerrillas who fought as dirty as they came. After the war, Jesse and his brother Frank formed the James-Younger Gang, robbing banks and trains across the Midwest. The newspapers of the day painted him as a folk hero, a rebel striking back against railroad barons and bankers who’d bled the everyday folks dry.
But the real Jesse James was as much a master of publicity as he was with pistol play. He sent letters to newspapers, spinning his own legend and taunting the law. He was fiercely loyal to his family and his gang. But, he could turn uncontrollably violent as quickly as a whipcrack if he felt betrayed.
Little-known fact:
Jesse James was so concerned about his public image that after one robbery, he wrote a letter to the Kansas City Times denying he’d been involved…while also hinting that he might have been. He understood the power of crafting myth and made sure his name stayed on everyone’s lips.
Jesse James’s life ended not in a blaze of glory, but with a coward’s bullet. He was shot in the back by a member of his own gang, Bob Ford, who hoped for a reward. Yet his legend grew even larger after his death, symbolizing resistance and the enduring power of myth that refuses to fade from American folklore. Even his tombstone reflects this admiration: “Jesse W. James, Died April 3, 1882, Aged 34 years, 6 months, 28 days, Murdered by a traitor and a coward whose name is not worthy to appear here.”
3. Belle Starr: The Bandit Queen
Belle Starr was a force of nature, and she made sure the world knew it. Born Myra Maybelle Shirley, she moved to Texas after the Civil War. She quickly found herself in the company of outlaws—first as a friend, then as a partner, and eventually as a leader. Starr was fiercely independent. She’d ride astride with pistols on her hips. It was her flair for high fashion that set her apart from the dusty crowd.
She ran with the likes of Jesse James and the Younger brothers, but she was never just someone’s sidekick. She organized cattle rustling rings, bribed lawmen, and managed to stay one step ahead of the law for most of her life. Her Oklahoma ranch became a safe haven for outlaws on the run.
Little-known fact:
Belle Starr was once convicted of horse theft. She spent time in the Detroit House of Corrections, where she reportedly charmed the warden and was released early for good behavior. She later joked that the food in prison was better than anything she’d had on the trail.
Belle’s mysterious murder—shot off her horse by an unknown assailant—only added to her legend. They never found her killer, and speculation still swirls about who pulled the trigger. Belle Starr’s story proves the West wasn’t just a man’s world. A woman with grit could become just as notorious as any outlaw.
4. Butch Cassidy: The Gentleman Bandit
Born Robert LeRoy Parker, Butch Cassidy was as charismatic as he was daring. Raised in Utah, he started as a ranch hand before drifting into crime. What set Butch Cassidy apart wasn’t just his string of robberies with the Wild Bunch. It was his easygoing manner and the way he treated his victims. He’d apologize for the inconvenience, crack a joke, and sometimes even hand out money to bystanders.
His partnership with the Sundance Kid became the stuff of legend, and together they pulled off some of the most audacious heists in Western history. When the law got too close, they fled to South America, robbing banks in Argentina and Bolivia and evading Pinkerton detectives at every turn.
Little-known fact:
Butch Cassidy once tried to go straight. He wrote a letter to the governor of Utah offering to surrender and serve a short sentence in exchange for a pardon. The governor ignored the request, and Butch went back to his old ways—a decision that sealed his fate.
To this day, no one knows for sure how Butch’s story ended. Some say he died in a Bolivian shootout; others claim he returned to the U.S. under an assumed name. The mystery is part of the legend, and it’s why Butch Cassidy’s story still fascinates anyone who dreams of life on the run.
5. Sam Bass: The Texas Train Robber
He wasn’t born an outlaw. Sam Bass started out as a hard-working cowboy and stagecoach driver. But after a failed attempt at gold mining in the Black Hills left him broke, Sam turned to robbing trains. His gang pulled off one of the biggest train heists in Texas history, making off with $60,000! A tidy fortune in those days.
Sam’s charm won him friends in low places and high ones, too. He’d regularly buy drinks for the whole saloon after a successful job and was rumored to have given some of his loot to struggling families along his route. But his luck ran out in Round Rock, Texas, when lawmen caught up to him. Mortally wounded in a gunfight, Sam died on his 27th birthday.
Little-known fact:
During his final days, Sam Bass was cared for by a local doctor and a handful of sympathetic townsfolk who admired his courage—even as he lay dying from gunshot wounds. He reportedly joked with his caretakers and refused to reveal the names of his accomplices, remaining loyal to the end.
Sam Bass’s brief, wild ride is a reminder that sometimes, the West made outlaws out of ordinary men—and that even in their final moments, some managed to hold onto their humanity.
6. Black Bart: The Polite Stagecoach Robber
Black Bart, whose real name was Charles Boles, was unlike any other outlaw in the West. British-born, he was educated, well-spoken, and always dressed to the nines—long duster, bowler hat, and a flour sack mask. He robbed Wells Fargo stagecoaches across California and Nevada, but never fired a shot or harmed a soul. Instead, he’d hand the driver a polite note demanding the strongbox, sometimes signing it with a bit of poetry.
Black Bart’s robberies were so theatrical that he became a media sensation. His wit and civility made him a favorite with the public, and his poems—left behind at the scene—only added to his mystique.
Little-known fact:
After his capture, Black Bart served time in San Quentin. Upon release, he told reporters, “I am through with crime.” He vanished from public record soon after, but a Wells Fargo detective later claimed to have seen him living quietly in San Francisco—proof that sometimes, even the most notorious outlaws just fade into the crowd.
Black Bart’s story proves that in the Wild West, brains could be just as dangerous as bullets—and that a clever outlaw could steal the show without ever firing a gun.
7. The Dalton Gang: Brothers Bound by Crime
The Dalton brothers—Grat, Bob, and Emmett—started out as lawmen, working as U.S. marshals in Indian Territory. But the lure of easy money and the thrill of rebellion pulled them to the other side of the law. The Dalton Gang became infamous for their daring train and bank robberies, often striking in broad daylight and leaving chaos in their wake.
Their most audacious plan was a double bank robbery in Coffeyville, Kansas, meant to cement their legacy. But the townspeople fought back, and in a furious gun battle, most of the gang was killed. Emmett Dalton survived, despite being shot 23 times, and later served time in prison. Ironically and poetically, he became a writer and a Hollywood consultant for a new movie genre called “westerns.”
Little-known fact:
Emmett Dalton lived long enough to see himself portrayed on the silver screen. He wrote a memoir and even appeared in early Western films, making him one of the few real-life outlaws to help shape the legend of the West from both sides of the law.
The Dalton Gang’s story is a cautionary tale about ambition, family loyalty, and the thin line between lawman and outlaw—a line that, in the Wild West, was all too easy to cross.
Conclusion: Why Their Legends Endure
When I look back at these seven outlaws, here’s what strikes me most: It isn’t just the drama of their crimes or the headlines they made. It’s the way they captured the restless, untamed spirit of the American West. Each one lived by their own code, daring to challenge the rules in a world where the law was often as rough as the land itself. They were rebels, yes, but also survivors. People who adapted, hustled, and sometimes paid the ultimate price for living on their own terms.
Their stories remind us that the West was never a place for the faint of heart. Grit, quick thinking, and a willingness to step into the unknown was what it required. These outlaws weren’t just running from the law; they were running toward something, too. Maybe freedom, maybe fortune, or maybe just a place to belong.
And even as the frontier faded and the world changed, their legends only grew, passed down in stories, songs, and now, in the digital campfires of the internet. They remind us that history isn’t always clear-cut, and sometimes the most unforgettable characters are the ones who refuse to fit neatly into any box. —☆
Who did I miss? The West was full of colorful characters, and I know there are plenty more legends out there. Let me know in the comments your favorite outlaw or one you think deserves a spot on this list.
2 comments
Bill Miner
Ah, he’s an interesting one. Known for his unusual politeness while committing robberies, he was widely nicknamed the “Gentleman Bandit.” And, he is reputed to have been the originator of the phrase “Hands up!” Maybe you can shed some light on that?