Welcome back to This Day in Scottish History. I’m your host, Colin MacDonald, and today, we journey back to October 10, 1820—a day that saw a bold, violent escape from Dumfries Tolbooth by one of Scotland’s most infamous thieves, David Haggart.

David Haggart, born on June 24, 1801, in Golden Acre near Edinburgh, was no stranger to a life of crime. His life was one of adventure, danger, and defiance of authority, but it all came to a tragic end with his desperate actions on this very day.

Haggart’s beginnings were humble. The son of a gamekeeper, he spent part of his childhood as a gillie, assisting Highland hunters, and received a good, if basic, education. Yet, even as a boy, Haggart was drawn to trouble. By 12, he had begun committing petty thefts, a habit that would soon consume his entire life.

In 1813, at the age of just 12, Haggart enlisted as a drummer boy with the Norfolk Militia stationed at Edinburgh Castle. His brief stint in the military would later inspire romanticized accounts of his life, such as in George Borrow’s Lavengro, where Haggart is described as a "wild, red-headed lad," brimming with strength and daring. But this idealized portrayal doesn’t quite match the real story of a boy who was far younger than Borrow imagined, and whose career as a soldier was short-lived. Haggart was discharged after just a year and returned to schooling, briefly apprenticing as a millwright.

When the firm he worked for went bankrupt in 1817, Haggart, now 16 and desperate, found himself turning to crime for survival. He quickly became a prolific pickpocket, burglar, and shoplifter, moving from town to town, racecourse to fair, across Scotland and northern England.

Alongside an Irish companion, Haggart’s criminal exploits proved remarkably successful in those early days. Together, they amassed over three hundred guineas in the span of a few months. But with success came risk. He was imprisoned six times and managed to escape four of those, marking him as a resourceful and determined outlaw.

His criminal life led him to Dumfries Tolbooth, a grim prison where Haggart’s cunning and boldness would once again come to the forefront. His time there was short-lived, however, as he plotted his most infamous escape, which would come at a tragic cost.

On October 10, 1820, David Haggart made his break for freedom from Dumfries Tolbooth. He had already gained a reputation for slipping out of tight spots, but this escape was different—it turned deadly. During his bid for freedom, Haggart struck down the tolbooth keeper, escaping the prison but leaving the keeper fatally wounded.

Fleeing the scene, Haggart’s next stop was Ireland, where he sought to disappear. He considered leaving for America or France to escape the law's long reach, but fate was not on his side. In March 1821, after a series of thefts, Haggart was arrested at Clough Market in Ireland. Despite his best efforts to remain incognito, he was recognized and extradited back to Scotland. His days of outrunning the law were finally over.

After his return to Edinburgh, Haggart was put on trial on June 11, 1821, for the murder of the Dumfries tolbooth keeper. Found guilty, he was sentenced to death. But even as he awaited his fate, Haggart’s story continued to captivate the public.

In the weeks leading up to his execution, Haggart managed to write and dictate his own autobiography, a detailed account of his life as a criminal. Titled The Life of David Haggart, it was edited and published posthumously with an appendix by the noted phrenologist George Combe. The autobiography paints a vivid picture of criminal life in early 19th-century Scotland, and much of it was written in Scottish thieves' cant, a language peppered with Romany words.

Haggart’s narrative is full of swagger, almost reveling in the life of a rogue. However, Lord Cockburn, a Scottish judge and contemporary of Haggart, claimed that much of the book was fabricated to make Haggart appear as more of a villain than he truly was. Regardless of whether his stories were true or embellished, The Life of David Haggart captured the public imagination and remains a curious document of a life cut short by crime.

David Haggart was hanged in Edinburgh on July 18, 1821, at the age of just 20. His brief life as a thief and murderer ended on the gallows, but his story continued to live on through his autobiography and later adaptations, such as the 1969 film Sinful Davey.

The story of David Haggart is a cautionary tale of a young man whose early descent into crime led him down a path of destruction. His life, as brief as it was, remains a window into the world of early 19th-century Scotland, a time of great change but also of significant hardship for many. Haggart’s choices, whether driven by circumstance or his own reckless spirit, led him to a violent end, but his tale has endured, a testament to the complexities of crime and punishment in his era.

As we reflect on the events of October 10, 1820, we are reminded of the turbulent lives of those who lived on the fringes of society, and the lasting impact they left on Scottish history.

Thank you for joining me today on This Day in Scottish History. I’m your host, Colin MacDonald. Be sure to tune in tomorrow for another fascinating episode. Haste ye back!

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