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What tactics did 17th and 18th century highwaymen use with more heavily guarded targets?
Sutemi
Highwaymen very rarely robbed anyone from the back of a horse. Horses are great big creatures that don't like a whole lot of noise, they tend to stamp and rear if the get frightened or they may just take off at a full gallop.
Highwaymen more times than not would work in pairs. They would find a place that was wooded on either side or they may just be standing at a cross roads on some busy highway. One would dismount and hold the other fellows horse. They would both be armed and would wait for a passing coach or traveler to come by (this was planned because coaches had timetables , even back in the eighteenth century) leveling there pistols and stopping the coach. If the coach driver made a break for it the highwayman holding the horses would release his oppo's horse and go after the coach normally shooting the lead horse (always the horse on the front left of the vehicle) or maybe even shooting the driver.
Once the coach was stopped they would rob those inside and make their getaway.
It was very rare for a highwayman or men to rob a coach single handed because you could pretty much guarantee that the driver or guard , even the passengers would have been armed. Firearms in the eighteenth century were very easy to get hold of and comparatively cheap.
They would also employ the use of the "footpad" nothing more than a thug to help on bigger jobs i.e mail coaches.
These coaches were heavily defended and it would have been easy for a highwayman to fall victim to a blunderbus or a hail of bullets from within the coach.
They also had camps set back in woodland where they would wait for a few days before moving on, horses were never kept too close by for fear that their whinning and stamping would give the position away. They would have been kept a good way away from the camp, but close enough for the highwayman to make a break for it if needed.
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