Famous outlaws, gangsters and bandits



The words highwayman and outlaw evoke in many minds the image of a masked, mysterious rider on horseback who robbed the rich and sometimes even gave to the poor. The English highwayman, in particular, was often seen as a dashing, carefree and exciting land pirate on horseback, certainly displaying more gallantry than the lowly criminal who slyly picked pockets or locks. The bold rider was assumed to show no trace of fear when face-to-face with the hapless traveller whom he waylaid. In legend, the English highwayman or ‘tobyman’, showed chivalry towards the fair sex and by doing so gained many admirers in their midst.

Several English highwaymen were fallen aristocrats, which made them even more fascinating to the public. Unfortunately, such cavaliers, or ‘gentlemen of the road’, who politely raised their hats before barking ’stand and deliver’, were rare. In reality, the vast majority of highwaymen and outlaws were uncouth and foul-mouthed. They included ruthless criminals, like Dick Turpin, who robbed purely for gain. Several were also murderers who showed little compassion towards their victims, especially if they thought they would be recognised later.

The term ‘outlaw’ had fewer romantic connotations. Originally, any man declared an outlaw could be hunted with impunity and even killed, as he was not entitled to legal protection. Later, the term came to mean any fugitive from the law.


Recent Articles

Posted at: 2008-10-15

Category: The Victims and the Booty

Such selectivity also occurred in Scotland during the late seventeenth and early eighteenth centuries, when Rob Roy held sway as an outlaw in the Highlands.


Posted at: 2008-10-15

Category: The Victims and the Booty

In England, rich travellers, merchants, moneylenders, lawyers and members of the court were attacked, robbed and deprived of gold and silver watches, jewellery, purses, baggage, gold lace, silks and money


Posted at: 2008-10-15

Category: The Victims and the Booty

Mail robberies could also prove profitable, but here, too, high risks were involved. Until the beginning of the nineteenth century, the mail in England was always carried by postboys on horseback


Posted at: 2008-10-15

Category: The Victims and the Booty

In the nineteenth-century American West, by contrast, ambushes of mail-coaches by bands of outlaws became increasingly frequent.


Posted at: 2008-10-15

Category: The Victims and the Booty

In England, travellers in stage-coaches and private carriages took many precautions against the likelihood of highway robbery. The rich often travelled with armed servants as guards.


Posted at: 2008-10-15

Category: The Victims and the Booty

In nineteenth-century Australia, with its much smaller population, only the occasional mail-coach in New South Wales was held up by bushrangers.


Posted at: 2008-10-15

Category: The Rise and Fall of Highwaymen

The type of outlawry prevalent in Australia, Britain and North America differed fundamentally from that in mainland Europe.


Posted at: 2008-10-15

Category: The Rise and Fall of Highwaymen

In Australia the activities of the bushrangers were marked by distinct phases, interspersed with periods of relative calm.


Posted at: 2008-10-15

Category: The Rise and Fall of Highwaymen

Towards the end of the eighteenth century, an accumulation of factors led to a fall in the numbers of highwaymen on the English roads.


Posted at: 2008-10-15

Category: The Rise and Fall of Highwaymen

In America, the westward expansion was so rapid that it was always a step ahead of a proper law-enforcing system.




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