Little is known about his early life, though it is believed he was born around 1678, in Kirkwall in the Orkney Islands, a group of small islands north of Caithness in northern mainland Scotland. Originally a shepherd, the introduction of flax led to the collapse of the wool trade on the impoverished islands and many of the Islanders took up smuggling.His career on the sea began smuggling contraband between Scotland and France, and later as a seaman on English privateers sailing between England and Jamaica. During the War of the Spanish Succession, Red Ben, an intelligent and physically imposing man described by contemporary’s as “seven feet tall with arms like tree trunks and eyes like steel, cold, hard. Had a shock of hair, red like the fires of Hell”  led a mutiny aboard the captured French ship La Téméraire and renamed it The Bonnie Prince. She was a two-hundred-ton frigate armed with twenty cannons, and he and its crew of 250 men ranged the west coast of Africa where Red Ben started in earnest on gaining a reputation as a fierce, unforgiving and exceedingly tight fisted pirate.
Red Ben wore a kilt and many an incredulous ships Captain was rendered fightless and impotent at the sight of his bulk arising out of the smoke of battle wearing what they assumed was a dress. To further the shock value as he assaulted a ship he would play his bagpipe, only reaching for his twin claymore swords as the battle closed. This image, which he cultivated, has made him the premier and only image of a seafaring swashbuckling Scottish pirate. In the following years Red Ben acquired a fearsome reputation for cruelty after repeatedly preying on shipping and coastal settlements of the West Indies and the Atlantic coast of North America. A running duel with the British thirty-gunned man-of-war HMS Warthog added to his notoriety.Unlike other contemporary pirates, Red Ben preferred to diversify, he did not believe in a single buried investment where capital was held in littoral environments, for later recovery, with securities of dead shipmates bones and single issue prospectus written in blood that detailed procedures to track the recovery of the plundered treasure.
Red Ben preferred to bank monthly, paying creditors on a 60 day merchants cycle ensuring he maintained maximum exposure to interest in his hard won doubloons and held various stocks including hedges. Red Ben would on Sundays take a form of ships pulpit and lecture his crew on the benefits of savings and thrift and impress upon them the value of investments. It was this habit that led to his downfall and the end of his swashbuckling days.Red Ben was eventually poisoned by the ships cook, with an arsenic laced Haggis.