Wanted: Dead or Alive – The 10 Most Feared Outlaws in Old West History

The Wild West was a land of lawlessness, where the crack of gunfire echoed through dusty streets and the frontier belonged to those who could fight – or run – fastest. Some of the most feared figures in American history emerged from this era, carving out legends through daring heists, ruthless gunfights, and bloody feuds. These men and women were more than just outlaws – they were survivors, tacticians, and, in some cases, cold-blooded killers.

Below are the ten most feared outlaws of the Old West, ranked not just by body count but by sheer infamy. These were the figures whose names sent chills down spines, whether they were robbing trains, shooting lawmen, or facing a lynch mob with a grin.

10. Sam Bass – The Gambler Who Bet Big and Lost

Sam Bass wasn’t born an outlaw – he was just looking for an easy fortune. After a rough start in life, he tried his hand at cattle driving, but the lure of fast money was too strong. When his cattle profits weren’t enough, he and his partner made off with $88,000 that didn’t belong to them.

His real claim to infamy, however, came from his train robberies. He and his gang pulled off the biggest heist in Union Pacific history, stealing over $60,000 in one go. But crime is a game of chance, and Bass eventually drew a losing hand when Texas Rangers tracked him down. Wounded in a shootout, he died on his 27th birthday – a young man who flew too close to the sun.

9. Belle Starr – The Bandit Queen Who Ruled with Charm and Bullets

Belle Starr wasn’t just any outlaw – she was one of the most cunning and elusive figures of her time. Born Myra Maybelle Shirley, she rubbed shoulders with the James brothers and the Younger gang, gaining firsthand experience in the art of outlaw survival.

Her specialty was horse theft, and she knew how to use both bribery and charm to keep the law at bay. Even after multiple arrests, she kept finding her way back to crime. But like many outlaws, she couldn’t outrun fate forever. In 1889, she was ambushed and shot dead while riding home, just two days before her 41st birthday. To this day, no one knows for sure who pulled the trigger.

8. James “Killer” Miller – The Church-Going Assassin

James Miller, also known as “Deacon Jim,” might have looked like a respectable citizen – he didn’t drink, smoke, or swear – but underneath his pious exterior was a ruthless killer-for-hire. He had a reputation for taking contracts on anyone, charging anywhere from $150 to $2,200, an impressive sum in those days.

Miller was a master of ambush tactics, often attacking his targets under the cover of darkness while wearing a steel plate under his coat to deflect bullets. Officially, he was credited with at least 14 kills, though rumors suggest the number was closer to 50. His reign of terror ended when a lynch mob decided to skip the trial and hanged him in an abandoned stable. His last words? “Let her rip.”

7. The Sundance Kid – The Phantom Gunfighter

Harry Alonzo Longabaugh, better known as the Sundance Kid, was a key figure in Butch Cassidy’s Wild Bunch gang. While he was rumored to be a deadly gunfighter, there’s no solid proof that he ever actually killed anyone. That didn’t stop him from becoming one of the most feared outlaws in the West.

He and Butch Cassidy became infamous for their long streak of successful train and bank robberies, outwitting law enforcement at every turn. When the heat got too strong, they fled to South America, where legend has it Sundance met his end in a Bolivian shootout. However, some claim he survived and lived out his years under a new identity.

6. William “Curly Bill” Brocius – The Drunken Gunslinger Who Crossed Wyatt Earp

Curly Bill was the kind of outlaw you didn’t want to run into at a saloon. A heavy drinker with a wild streak, he became the leader of the Cowboys gang in Tombstone, Arizona. His most infamous moment came when he accidentally (or maybe not so accidentally) shot and killed Marshall Fred White.

Despite being acquitted thanks to the testimony of Wyatt Earp, Curly Bill’s feud with the Earps continued to escalate. Eventually, Wyatt hunted him down in the Arizona desert, where they had a legendary showdown. Wyatt walked away, Curly Bill didn’t.

5. Butch Cassidy – The Gentleman Outlaw

Unlike some of the more bloodthirsty figures of the Wild West, Butch Cassidy preferred to rely on charm and strategy rather than violence. He built the Wild Bunch, one of the most successful outlaw gangs in history, pulling off a string of train and bank robberies that kept law enforcement scrambling.

Despite his cunning, Butch’s luck eventually ran out. Most historians believe he was killed in a shootout in Bolivia, but like his partner, the Sundance Kid, there are whispers that he returned to the U.S. and lived under an assumed name.

4. John Wesley Hardin – The Preacher’s Son Turned Gunfighter

John Wesley Hardin was named after a Methodist preacher, but that’s about where his connection to religion ended. By the time he was a teenager, he had already killed multiple people, including a lawman.

Hardin was notorious for his hot temper and fast draw, earning a reputation as one of the deadliest men in Texas. He was even rumored to have shot a man just for snoring too loudly in a hotel room. After spending 17 years in prison, he tried to go straight as a lawyer – but old habits die hard. He was eventually shot in the back while playing dice.

3. Cole Younger – The Outlaw Who Found Redemption

Cole Younger started his outlaw career after his father was murdered by Union soldiers, joining forces with the James brothers to exact revenge. Together, they carried out numerous bank and train robberies across multiple states, earning a fierce reputation.

His luck ran out after a botched robbery in 1876. Rather than facing the noose, he and his brothers pleaded guilty and were sentenced to life in prison. Amazingly, he was paroled after 25 years and spent his later years as a reformed man, touring the country and telling his story.

2. Billy the Kid – The Young Gunslinger Who Became a Legend

Billy the Kid is arguably the most famous outlaw in Old West history, but his story is more complex than the legend suggests. While often depicted as a ruthless killer, he was more of a survivalist than a cold-blooded murderer.

Born into hardship, he turned to crime as a means of survival. He was caught up in the Lincoln County War, where he gained his reputation as a gunfighter. After years of dodging the law, he was finally cornered and shot by Sheriff Pat Garrett. Some believe he survived, but the evidence suggests the legend ended that night.

1. Jesse James – The Robin Hood of the Wild West

No outlaw’s name is more synonymous with the Wild West than Jesse James. A former Confederate guerrilla fighter, Jesse formed the James-Younger Gang and spent years robbing banks, trains, and stagecoaches.

Jesse became a folk hero, with newspapers portraying him as a noble outlaw fighting against corrupt corporations. In reality, he was ruthless and dangerous, but his legend only grew after he was betrayed and shot in the back by Robert Ford, a fellow gang member. His mother made sure his epitaph reflected his tragic end: “Murdered by a traitor and coward whose name is not worthy to appear here.”

Legends Never Die

The Old West was a brutal and unforgiving place, where only the boldest survived and the deadliest became legends. These outlaws, each with their own code and motives, shaped an era of lawlessness that still captures our imagination today. Some were ruthless killers, others were charismatic thieves, but all left behind stories that blurred the line between fact and folklore. 

Their names live on, not just in history books, but in films, novels, and the collective memory of the American frontier. Whether they were villains or antiheroes depends on who’s telling the tale, but one thing is certain – these gunslingers made their mark on the Wild West, and their legends will never die.