In his younger days, he was a blacksmith in North Devon and was so skilled he won an award for his craftmanship at the North Devon Show.
However, later on he got into a legal brawl with a local wealthy family - the Bampflydes. He lost everything, including the girl he was due to marry. Her father refused to allow the marriage to go ahead.
So what was a man to do? He turned to highway robbery and was very successful straight away. However, he set himself apart from other robbers by treating his victim with great courtesy and was not violent unlike others. He also notably only stole from very the wealthy and left poorer folk alone and was known to be generous to the poor.
Many traps were set to try and catch him, but he evaded capture with the help of his horse - a strawberry roan mare called Winnie who would come to his aid when he whistled.
|A Strawberry Roan|
One time a group of vigilantes gathered to lay wait for him. Tom, realising that they dithered and were unsure who he was, asked the amateurs who they were waiting for. They told him about the famous highwayman and allowed him to join them. Tom inspected their firearms and told them to discharge their weapons because the gunpowder was damp. They did this, and Tom duly robbed them of their purses.
One of Tom's victims was Sir Richard Bampfylde, the man who had left him destitute. However, Tom returned Sir Richard's money to him saying that it was not customary for one robber to steal from another.
Eventually Tom was captured by a trap set for him. In a tavern, a constable dressed as a beggar was offered a drink by Tom. The beggar knocked Tom to the ground and bound him. Tom tried to whistle for Winnie, but the horse had been killed in the stable. It is thought Tom was hanged, but no record of his execution has been found. He was immortalised in R D Blackmore's book "Lorna Doone" as a character who married Jan Ridd's sister and who obtained a pardon from King James II.