I have always had a strange interest in American outlaws but not known why. Maybe it’s just because American outlaws have tended to become folk heroes and local legends. From the wild west to the depression era. From Jesse James to Butch Cassidy. From Texas to Alaska. We look at some of histories best and most notorious American outlaws and gangsters and count down through the most fearless examples. These are the stories that forged an era and inspired thousands of works of fiction. But how much of their stories is actually true?


10) Belle Star (1848 – 1889):

 

With her famous pistol

With her famous pistol

 

Belle Star was one of a handfuls of female outlaws. As a child she was associated with famous outlaws like Jesse James and the Younger Brothers. When she grew older, she earned the nickname “Queen of the Oklahoma outlaws”. She was notorious for being a crack shot and for riding sidesaddle with two pistols.

Together she and her associates pulled off dozens of heists. In 1889 she was shot to death aged 40. The killer was never identified and she has since been popularized in fiction. She was famous for having romantic affairs with other outlaws. Many of them died before she did. So she just found someone else.


9) Butch Cassidy (1866 – 1908?): 

 

The man with the plahn

The man with the plan

 

Butch Cassidy was a notorious train and bank robber. On June 24 1889, he and several others robbed 21 thousand dollars from a bank. And this was just the beginning, they continued robbing shit for many years. In 1901 he was forced to flee the country in order to evade authorities. He boarded a ship to Argentina, before later moving to Bolivia. This is where he is believed to have been killed.

Although, several of his relatives claimed to have seen him since. As his body has never been found, some believe he escaped justice and lived on.


8) John Dillinger (1903 – 1934):

 

Dillinger judges you

Dillinger judges you

 

John Dillinger led his gang to rob 24 banks and even 4 police stations. He was the most notorious outlaw of his time and was even used by the government to explain the formation of the FBI. In 1934, federal agents eventually shot him down.

He famously once escaped from crown point jail using a fake gun crafted from wood. The newspapers of the time were boasting that crown point was escape proof. So when Dillinger broke out, a lot of people got in trouble. After the break out he went straight back into organized crime with his friends. The amazing thing is that the government genuinely spent more money pursuing him than he stole from banks.


7) Sam Bass (1851 – 1878):

 

The mighty mustache of crime

The mighty mustache of crime

 

Sam Bass was an old west train robber who resorted to crime after failing in legal business. As part of a gang he robbed a train in 1877. They took 60 thousands dollars, which remains the single biggest robbery on the union pacific railroad. He evaded the Texas rangers for years up until they managed to surround him in 1878, and fatally wounded him.

He died on his 27th birthday in police custody. Bass has recently been portrayed in many films and tv shows.


6) John Hardin (1853 – 1895):  

 

The classic pose

The classic pose

 

John Wesley Hardin wasn’t just an outlaw. He was an icon of the old west. He was basically just a gunfighter who loved nothing more than a good duel. When he was sent to prison he claimed to have killed 42 men. Which is a fuck load. He was released from prison in 1878 and shot dead in a saloon one year later.

He soon became a controversial folk hero. Controversial, because he leaned more to the right than a paraplegic holocaust denier.


5) Machine Gun Kelly (1895 – 1954):

 

What a mug!

What a mug!

 

Machine Gun Kelly was a gangster during the prohibition era. He gets his nickname from the Thomson sub-machine gun, as it was his favorite weapon. In 1933 he kidnapped an oil tycoon and held him ransom for 200 thousand dollars. This was the crime he was arrested for but he was also guilty of bootlegging and armed robbery.

After a long trial he was sent to Alcatraz. Which was basically just a clubhouse for American outlaws and gangsters.


4) Babyface Nelson (1908 – 1934):

 

Hard to tell his age here

I wonder how he got his name

 

Babyface Nelson was an extremely violent bank robber. He led several criminal gangs and even assisted John Dillinger in his famous ‘wooden gun’ prison escape. He killed more active FBI agents than anyone else. Which led to him topping their most wanted list and becoming public enemy number one.

At the age of 12 he shot someone in the jaw; 13 years later he died in a shootout. Even after the FBI killed him, he was a sort of robin hood figure of the depression era. Few American outlaws reach his level of infamy – and for good reason too!


 3) Soapy Smith (1860 – 1898):

 

Jefferson Randolph here

Jefferson Randolph here

 

One of the most notorious American outlaws is Soapy Smith. Soapy Smith was an old west crime boss but also a con artist. He is famous for organizing criminal activity in Colorado and Alaska, running auction houses and gambling halls that were geared towards scamming people. He would also rig elections for his political allies.

He lived and died like a true outlaw, being shot to death in 1898.


2) Jesse James (1847 – 1882):

 

his age here is unknown

his age here is unknown

 

Jesse James was world famous as one of the best in the west. After fighting on the losing side during the American civil war he robbed banks, stagecoaches and trains. He was very active up until 1876 , when several members of his gang were either arrested or killed.

In 1882 he was shot in the back of the head by his friend, Robert Ford. Ford was later killed by another outlaw.


 

1) Billy The Kid: 

 

Billy_the_Kid_tintype,_Fort_Sumner,_1879-80

 

I think Billy the kid has been enshrined in popular culture more than any other outlaw. Legend says he killed 21 people. But while alive he was largely unknown. It was only in 1881 that he gained national fame when a bounty was placed on his head. He was soon arrested and sent to jail

Two days before he was due to be hanged, he escapes. He killed two men and escaped on horseback. This is the single event that cemented him as an American folk hero.

His story is shrouded in mystery. In fact, there is only one existing photograph of New Mexico’s most feared outlaw.


So that concludes our list of the top 10 most fearless American outlaws.


OUR VIDEO ON THIS:


 

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