Highwayman is a seventeenth-century English word meaning a thief who stops and robs people travelling by road. Back when the word was new, they stole pretty much what the same type of criminal would steal today - whatever the travellers might be carrying which was of value for use of the thief or for sale or exchange.
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The travellers who passes through the Highway.
Highwaymen rob people because they want their money or valuables. They are robbers for the same reasons any other criminal steals.
Same reason as any other financial/property crime - stealing seemed like and easy/ only way to make some money.
highwaymen drunk ale
The word highwayman is first attested from the year 1617. The term "highwayman" is mainly applied to robbers who traveled on a horse, as opposed to those who robbed on foot (foot-pads). Mounted robbers were widely considered to be socially superior to foot-pads.
Highwaymen that were the worst and most dangerous and came from Sussex.
Highwaymen were sentenced to death by hanging. They were hanged OR shot if they were caught.
They could of been but there is no really right or wrong answer to this.