Vermont's Captain Thunderbolt: A Mysterious Schoolteacher With A Secret Past

By | December 29, 2021

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A masked highwayman on horseback robs a pedestrian. Date: 18th century. (Hulton Archive/Getty Images)

In the early 1820s, a well-dressed gentleman arrived in the Vermont town of Brookline, becoming the community's schoolmaster and, later, a country doctor. Over the years, however, the townspeople whispered their suspicions that the man they knew as Dr. John Wilson may have been a notorious Scottish highwayman who had terrorized the Irish countryside.

Captain Thunderbolt

In the early 1810s, the highways of Scotland, Ireland, and England were under siege by highwaymen, robbers who terrorized travelers in the countryside. Two of the most notorious highwaymen were a duo known as Captains Thunderbolt and Lightfoot, A.K.A. John Doherty and Michael Martin. The pair had a code of ethics that set them apart from typical thieves: Much like Robin Hood, the Captains only robbed wealthy travelers, never killed anyone, were polite and courteous, and refused to steal from ladies. By 1819, the fuzz was hot on their trail, so Doherty and Martin disguised themselves as Quakers and made their way to Dublin, where Martin hopped a ship to New York City while Doherty supposedly headed for the West Indies, where he intended to drop the Captain Thunderbolt persona and go straight. It appears he did go to the West Indies for a time, then to Canada, and then, maybe, to Vermont.

In the U.S., Michael Martin continued his life of crime, but he was soon caught and sentenced to death by hanging. On the cusp of his execution, Martin penned a confession, detailing his exploits with Doherty and describing his partner in great detail, including his height, appearance, injuries he'd endured, education as a physician, and possible location in the West Indies. The confession didn't help Martin, but it was printed into a booklet by a local publisher and circulated around New England. Many people read it ... including people of Brookline, Vermont.

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Brookline, Vermont in 2016. (Magicpiano/Wikimedia Commons)

A Mysterious Stranger

As Michael Martin held folks up in New England, a mysterious stranger arrived in Brookline. He told the people there that he was originally from Scotland (which checked out, as he spoke with a thick brogue), had spent some time in the West Indies, and was trained as a doctor. Dr. John Wilson, as he introduced himself, offered to serve as the community's schoolmaster.

He soon ordered the construction of a strange, round schoolhouse atop a small hill, which had windows all around so he could see anyone approaching his school from any direction. It was never clear why such a feature was necessary, and that wasn't the only odd thing about Wilson. He walked with a limp, though he obviously tried to conceal it, and wore a scarf around his neck at all times, even in the dead of summerAfter Martin's confession circulated through town, the people of Brookline began to wonder about their mysterious newcomer. Wilson was reluctant to talk about his past, which only added to the mystery, but he scoffed at Martin's confession.

Still, no angry mob ever came after Wilson. He lived in Brookline for nearly three decades, but after his death in 1847, an examination of his body revealed scars on his neck and leg consistent with injuries described by Martin and a set of English pistols were found among his belongings, along with other assorted firearms. Most of the evidence linking Wilson to Captain Thunderbolt, however, was circumstantial. The people of Brookline will probably never know if they sheltered an infamous outlaw for close to 30 years, but that schoolhouse sure does bring in a lot of tourists.