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According to legend Highwaymen operated by galloping after a mail coach or laying in wait then riding out and with a brace of pistols and crying "Stand and Deliver robbed the coach.

Nice idea, if you want to believe it.

Highwaymen very rarely used horses in robbing a coach. They would of course use a horse to get to wherever the coach was passing but would hold the coach up on foot, usually working in pairs. One would hold the coach up at gun point, whilst the other held the horses a little way off so as they could make their escape once the deed had been done.

The problem with holding anything up on horseback is that horses are big creatures and even if well trained will move about. A horse that stamps about while his rider has a pistol pointing at a coachman in one hand and the reins in the other is likely to come to grief very quickly.

It was far more practical to hold the coach up on foot. If the driver decided to make a break for it then the highwayman would either shoot him or the lead horse. The lead horse is the one on the left front of the rig.

Also it is wise to remember that just because a mail coach was the prime target of any highwayman, they did carry passengers and most likely they would be armed, weapons especially flintlocks were readily available back in the 18th century. So holding the reins in one hand a pistol in the other and trying to hold up a coach suddenly seems to be a bit tricky.

No they mostly robbed coaches on foot.

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