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4 Wild West Outlaws Who Wreaked Havoc Across America

What defines the Wild West?… Train robberies? Shootouts? Cattle rustling? Horse stealing? 

The frontier was a mix of indigenous populations, newly arrived immigrants, and fourth-generation colonists. It was a period when businessmen and farmers worked side by side.

A time when steam trains were competing with horse-and-cart, when the camera and light bulbs were invented, yet so many couldn’t afford to put food on the table. It was a civilized society in many ways but so backward in others.

And in today’s world, the term “Wild West” has become synonymous with “Wild West Outlaw.”

When no actual judicial system existed and deadly duels most often resolved disputes, the frontier became a breeding ground for criminals who robbed trains and banks, rustled cattle, and killed law enforcement officers.

And the most infamous outlaws of the Wild West have been somewhat romanticized as daring robbers since their stories first hit early American media.

In many ways, their portrayals have been shaped in TV shows, Hollywood films, and novels to fit the frontier models of rugged individualism and pioneers. Jesse James and Billy the Kid, for example, personify that rebellious nature.

As Americans, we tend to overlook the crimes and see the romance of the rebel. These are the stories of 4 Wild West outlaws. Even though many led short and violent lives, they’ve surely left an enduring mark on the frontier.

Wild West
Photo by Digital Storm at Shutterstock

Billy, The Kid

1859 – 1881

Before he became an infamous Wild West outlaw, Billy the Kid was an orphan called Henry McCarty. Born in NYC in 1859, he lost his father as a young child, moved west with his mother, and became an orphan by age 15. This was when McCarty began his life of crime.

Henry started getting into trouble for petty theft, and in 1875, he went to jail for stealing clothes from a Chinese laundry. According to History, his Wild West should have ended there, but the kid escaped jail.

Now officially a fugitive from the law, he reveled in his new outlaw life, and he soon became known for deeds far worse than stealing clothing.

Soon after, McCarty found work as a ranch hand in Arizona, where he earned the nickname “Billy, the Kid” for his boy-like appearance and spent his free time drinking and gambling. He killed his first man in 1877, and from there, his infamy grew.

After moving to become a cowboy on a ranch in New Mexico, he became a central player in the so-called Lincoln County War. Despite all this chaos, McCarty continued to evade jail.

After shooting yet another person, being arrested, and receiving a death sentence, he fled from jail again. But in the process, he killed two law enforcement officers and escaped with a stolen horse.

Despite the dramatic getaway, his life soon ended on July 14th, 1881. At just 21 years old, Sheriff Pat Garrett chased him to Fort Sumner, New Mexico, and shot the infamous outlaw to death.

Wild West
Photo by Antonio Gravante at Shutterstock

Jesse James

1847 – 1882

Jesse Woodson James was one of the most famous American Wild West outlaws in history. He was a bank and train robber and the leader of the James–Younger Gang. Born in 1847 and raised in western Missouri, James and his slave-owning family had strong Southern sympathies.

As the head of the James-Younger Gang, Jesse played a pivotal role in their successful string of stagecoach, train, and bank robberies. Ironically, he was and still is constantly looked at as a kind of Robin Hood of the Old West.

But there really isn’t any historical proof he gave back to the poor. His legendary reputation is most likely because of newspaper editor John Newman Edwards, who was a Confederate sympathizer.

He wrote Jesse James’s Robin Hood fable. “We are not thieves. We are bold robbers,” Jesse wrote in a letter Edwards later published. “I’m proud of the name, for Alexander the Great was a bold robber, and so were Julius Caesar and Napoleon Bonaparte.”

In 1881, the Missouri governor issued a $10,000 reward for the capture of Jesse and his brother Frank James.

On April 3rd, 1882, at age 34, James was fatally shot in the back of the head by one of his accomplices, Robert Ford, who was later found guilty but pardoned by the governor.

Butch Cassidy

1866 – 1908

Born Robert LeRoy Parker in Circleville, Utah, this famed Wild West outlaw grew up dirt poor as one of 13 children of a family of devout Mormons.

In his younger years, working on a nearby ranch to help his family, legend has it that he met Mike Cassidy, a cattle rustler, who taught him how to make “a better, at times, distinctly dishonest, living.”

Moving to the gold rush town of Telluride, Colorado, Butch, with three other men, on June 24th, 1889, committed the first crime attributed to him, a bank robbery, during which the trio ran away with $20,000.

Adopting his new name and hiding out in Wyoming, he started adding some outlaw cowboys to his team, known in the media as the “Wild Bunch.” This included Harry Longabaugh, aka the “Sundance Kid.”

After 18 months in prison for horse theft in 1896, Butch Cassidy’s Wild Bunch stole from a Montpelier, Idaho bank, pocketing $7,000.

The gang went on to commit a few other robberies in the Southwest, as well, including $70,000 during a Rio Grande train robbery in New Mexico. Butch and the Sundance Kid ultimately fled to Argentina with the authorities on their trail.

Eventually, though, Cassidy returned to robbing trains and payrolls until his alleged death in 1908. Why do we say ALLEGED death?

Well, many Wild West historians believe that Butch and Sundance, immortalized in the Robert Redford and Paul Newman movie, actually perished in a shootout in Bolivia. Still, others theorize that the pair escaped, living their lives under different names.

Photo by Nong2 at Shutterstock

Doc Holliday

1851 – 1887

John Henry Holliday never actually planned on becoming a Wild West legend. He was born on August 14th in Griffin, Georgia, and he originally wanted to become just an ordinary dentist.

But illness and perhaps even fate had other plans. Shortly after Doc Holliday finished dental school and opened his own practice, he was struck with tuberculosis.

When he was told he might just have a few months to live, Doc took his physician’s advice and moved out west, hoping the dry air would extend his life. But instead, it introduced the young dentist to gambling, saloons, and life as a Wild West outlaw.

Holliday often got in trouble for fighting and, to protect himself, carried a gun and allowed his reputation as the “Deadly Dentist” to take hold. But Holliday finally lived up to the name in 1877 when he stabbed a cheat in the stomach and was arrested in Fort Griffin.

Unlike most Wild West outlaws, however, Holliday found his way back to the simple life. After moving to Dodge City with Big Nose Kate, the love of his life, he practiced dentistry again.

And he befriended the legendary lawman Wyatt Earp. When Earp and his brothers moved to Tombstone, Arizona, in 1879, Holliday went with them.

There, he aided the Earp brothers as they battled to contain Tombstone’s criminals and fought beside them in the 1881 Gunfight at the OK Corral, leading to three outlaws’ deaths.

Just six years later, Doc Holliday’s tuberculosis caught up to him. The “Deadly Dentist” moved to Glenwood Springs, Colorado, in hopes that the hot springs would improve his health. But sadly, he died at the age of 36.

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