From highway robbers to Wild West bandits and fearless freedom fighters, pass your own verdict on some of history’s most audacious and enduring criminals.
10 Jesse James 1842-1882
Born in Kearney, Missouri, to hemp farmers Robert and Zerelda James, the life of Jesse James and his brother Frank would change for ever when, in the summer of 1863, Union soldiers attacked the Confederate James’ farm.
Angered by the brutality of the Union, Jesse and Frank turned to crime and, following the Confederacy’s defeat in spring 1865, led their newly formed James Gang on a vendetta against any institution the North had laid its hands on. Banks, trains and more were all considered fair game to Jesse and his gangmates, often with gruesome outcomes for those involved beyond just theft. The notoriety of the James Gang spread far and wide in the Confederate states, with many declaring them heroes and even modern-day ‘Robin Hoods’. In reality they kept most of their plunder for themselves, and were not adverse to resorting to murder to achieve their goals. Overall it’s now thought that they were responsible for dozens of robberies and numerous murders, with their stolen money totalling in the thousands of dollars. On 3 April 1882, however, Jesse was betrayed by gang member Robert ‘Bob’ Ford who shot him in the back of the head to claim a sizable reward, thus bringing an end to Jesse James’s short but illustrious career as an outlaw.
9 Hereward The Wake Circa 1035 Circa 1072
Also known as Hereward the Outlaw, this notorious rogue from the Middle Ages has been written into many fictitious legends of times gone by, but his existence is all but a certainty.
A Saxon descended from Danes he was exiled by King Edward the Confessor to Europe aged 14. When William the Conqueror became king of England in 1066, Hereward returned. With the Normans having slain his brother and taken his family’s land, Hereward wreaked vengeance upon the French and displayed the heads of his fallen enemies above his door.
After a failed attempt to take the throne in 1070, Hereward was forced to live as an outlaw in the forests of the Fens in eastern England. He was a constant thorn in King William’s side, however, and ultimately the king agreed to give Hereward’s land back in return for a truce in hostilities.
“ Hereward displayed the heads of his fallen enemies above his door”
8 Dick Turpin 1705-1739
This highway robber has gone down in history as one of the most notorious British legends, but Dick Turpin’s crimes are often portrayed in a much more charming light than the grisly reality.
Born in Essex, England, in 1705, he began his working life as a butcher before falling into a gang. By 1735 he had become a highwayman, holding up stagecoaches and robbing the rich of their money and valuables. In 1737, however, he was recognised by servant Thomas Morris and things quickly escalated. After Turpin shot Morris dead, a Royal Proclamation was issued for his capture.
After changing his identity to a horse dealer by the name of John Palmer and moving to the village of Brough in East Yorkshire, Turpin was eventually arrested for shooting a cockerel and stealing horses.
However, his true identity came to light when his handwriting was recognised in a letter which he’d sent to his brother-in-law, and it wasn’t long before he was found guilty of his former crimes and hanged on 7 April 1739. His misdeeds as a highwayman may leave some to remember him as a lovable rogue, but make no mistake, this robber had a dark side – and blood on his hands.
7 Belle Starr 1848-1889
Belle Starr was a renowned outlaw from the American ‘Old West’. She was born near Carthage, Missouri, in 1848, receiving a classical education – learning how to play the piano, for instance. But from an early age she was involved with some of the country’s most notorious criminals, including Jesse James, and her reputation as one of the few female outlaws would earn her the nickname ‘The Bandit Queen’.
She would ride her mare, Venus, stealing horses and cattle as she drifted through the fringes of the Wild West. She became involved in the Starr clan, an outlaw Cherokee family, after the death of her first husband in 1874. Here she was the front for the bootleggers among their clan, but was captured along with her second husband for rustling horses – serving nine months in prison as punishment. After a life of crime and a string of husbands who fell foul of the law, Belle Starr was shot in the back by an unknown assailant in 1889.
6 Al Capone 1899-1947
Born in Brooklyn, New York, on 17 January 1899, Alphonse ‘Al’ Capone would go on to become one of the most infamous American gangsters. His squalid beginnings, coupled with a timid and lawabiding family, hid what he would become.
At the age of ten Capone met gangster Johnny Torrio, who taught him how to run a racketeering business. Eight years later he was hired by the brutal gangster Frankie Yale as a bouncer and bartender, receiving his famous scar in an altercation on the job. In 1925, following the serious injury of Torrio in an assassination attempt, Capone was appointed head of the Chicago mafia. He ran the streets with his mob and had several highranking officials across the city on his payroll.
After a failed attempt at killing Bugs Moran – a member of a rival Chicago gang – in 1929, Capone was tracked down by Eddie O’Hare and the IRS and sentenced to 11 years in prison for tax evasion on 24 November 1914 (partly served at Alcatraz). After his release in 1939, he spent time in hospital before moving to his estate in Miami, FL, where he died of a stroke and pneumonia – but not before having his former lawyer O’Hare killed for his betrayal.
5 Ned Kelly 1855-1880
Ned Kelly is one of the most infamous outlaws in Australian history. Born in Victoria he had numerous run-ins with the law as a youth. In fact, by the age of 19 he’d served over three years in prison, primarily for stealing a horse.
It was at 22 years old that the life of an outlaw really begun for Kelly. He was accused of shooting a police officer in the hand, forcing him to go into hiding with his brother Dan. The two teamed up with friends Joe Byrne and Steve Hart and, when Kelly’s mother was arrested and sentenced to three years in prison, his hatred of the law only intensified. Kelly and his gang ambushed a police camp a few months later resulting in the deaths of three policemen, after which a bounty was placed on Kelly and his gang in November 1878. Despite this, the gang would go on to rob a number of banks in the ensuing months, becoming notorious across Australia.
Following a standoff with police at a hotel in 1880, Kelly – wearing his now famous cobbledtogether plate armour and metal helmet – found himself alone after the death of the other members of his gang. He was sentenced to be hanged on 11 November 1880, aged just 25.
4 Boudica Unknown-Circa 61 CE
In the face of brutality from the Roman Empire which conquered southern England in 43 CE, one female outlaw stood strong and led her Celtic tribe against their oppressors. Boudica was the wife of Prasutagus, the head of the Iceni tribe in east England, earning herself the name ‘Queen of the Iceni’. Following the Roman invasion of Britain, two Celtic kings were allowed to continue to reign over their domains – one being Prasutagus. But following his death around 60 CE, the Romans laid claim to Iceni territory.
After numerous atrocities against her people, Boudica led an uprising against the Romans. She took 100,000 Iceni to the Roman capital in Camulodunum (now Colchester) and drove the invaders out, burning the city to the ground.
She marched on to destroy Londinium (now London) and Verulamium (now St Albans) before, weary from battle and travelling, her army succumbed to a Roman counterattack.
Legend has it that, to avoid capture by the Romans, Boudica killed herself with poison – an inglorious end to an outlaw who struck a legendary blow to the mighty Roman Empire.
3 Pancho Villa 1878-1923
Not all of the outlaws in our roundup stuck purely to a life of crime. Some, like Mexican Doroteo Arango – better known as Pancho Villa, began as a renegade but ‘went straight’ later on, albeit in revolutionary circumstances.
After hunting down and killing a man he believed had sexually assaulted his sister, Villa lived life as a bandit in the hills of Durango, Mexico. After dices with the authorities, however, Villa mixed the life of an outlaw with legitimate pursuits. He was later convinced to join the Mexican Revolution and led armies against the government of the time. But when America intervened in 1916 – which coincidentally had been hunting for Villa due to his role in the revolution – Villa’s power began to wane and he ultimately surrendered in exchange for a large swathe of land in Chihuahua. Villa was assassinated while he was driving in July 1923.
“ Pancho Villa mixed the life of an outlaw with legitimate pursuits”
2 Phoolan Devi 1963-2001
Phoolan Devi was the ‘Bandit Queen’ of the East, or more specifically India. Devi was born in the village of Ghura ka Purwa to a relatively poor family who were treated badly by those of a higher caste. Aged 11 Devi was married to an older man who abused her, but she managed to escape to work with her father and sister. She had a fiery temper, typified by her destroying a house they had built after the owner refused to pay for it.
She suffered further abuse – this time at the hands of some of her villagers – before leaders of the village handed her to a bandit gang in the hope they would be rid of her. It was a fatal error because, as it turned out, she became an integral member of the gang. She returned to the village and murdered all those that had abused her – a killing spree known as the Behmai Massacre.
In 1983, Devi and her gang surrendered after committing further crimes. She spent 11 years in prison before becoming an MP in 1996. However, she was assassinated in 2001 by a man claiming vengeance for the Behmai murders.
1 Billy The Kid 1859-1881
Perhaps no name evokes the image of an outlaw more than that of Henry McCarty – more commonly known as Billy the Kid. His death at such a young age (21), coupled with some less than savoury pursuits, has seen this figure become a staple fixture of the American Wild West.
Although born in New York City, as he grew up McCarty and his family moved across the country to New Mexico via brief stints in Indiana and Kansas. With the death of his mother in 1874, McCarty soon turned to a life of crime. He was apprehended for a robbery at the age of 16 but fled to Arizona, where he became a prominent horse rustler.
A string of deaths followed McCarty. It’s often said that he killed 21 men – one for each year of his life – although his true head count is thought to have been closer to nine. His last kills, however, were two guards holding him hostage after he had been found guilty of killing Sheriff William Brady. McCarty was gunned down at Fort Sumner, New Mexico, in 1881, bringing an end to a short-lived career but leaving a long-lasting legacy.
“ It’s often said that he killed 21 men – one for each year of his life”