1690: On a moonlit stretch of the Hampshire Downs, a nobleman’s carriage jolts to a halt as the notorious highwayman Old Mobb steps into its path.

Dressed in women’s finery and armed with a pistol, he greets his quarry with an elaborate curtsey. “Your purse or your life, kind sir,” he quips, voice dripping with mock politeness.

The stunned nobleman reluctantly scribbles a cheque for £150 under the highwayman’s amused gaze.

“I trust your goldsmith in Exeter is as reliable as your wit,” Mobb jests, leaving the hapless victim tied under a hedge as he rides off into the night.

Such was the flair of Old Mobb, the enigmatic and theatrical outlaw who haunted southern England’s roads in the late 17th century.

Born Thomas Sympson in Romsey around 1650, his exploits elevated him from mere robber to a legend of cunning and panache. Unlike many of his ilk, Mobb didn’t just rob; he performed, often regaling his victims with witty verse or biting observations.

One of his most infamous encounters involved the Duchess of Portsmouth, Charles II’s French mistress.

Capturing her in her coach, he delivered a blistering diatribe against her status and nationality, declaring himself “king here” and confiscating her jewels as tribute.

Even Lord Jeffreys, the feared Hanging Judge, couldn’t escape Mobb’s sharp tongue. When Jeffreys threatened him with damnation, Mobb retorted that he’d stand as good a chance at salvation as the judge himself, whose hands he said dripped with the blood of innocents.

Mobb’s flair for mockery and fearless defiance turned even his crimes into a kind of rebellious theater, captivating the public imagination.

Hanged at Tyburn in 1690 (or perhaps 1691, records are murky), Old Mobb’s legend endures. Was he a scoundrel, a hero, or a figment of folklore? Perhaps all three.