The novel Princess Bride by William Goldman features a secret pirate franchise called the Dread Pirate Roberts. Goldman based the Dread Pirate Roberts on the greatest European pirate captain of the 18th Century, Bartholomew Roberts of Wales.
Accounts vary on exactly when John Roberts went to sea, probably between the ages of 10 to 13. He spent most of his life as a sailor, serving in the Royal Navy and merchant vessels, the last being a junior officer aboard the slave ship Princess of London.
After being captured by pirates, he was coerced into joining their crew when they realized that he was a skilled navigator. The captain, Howell Davis, who was also Welsh, undoubtedly wanted someone he could trust who spoke his own language. It's thought that after joining the pirates Roberts changed his name to Bartholomew Roberts as a "nom de guerre."
Six weeks later, the Portugese killed Davis. The crew elected Roberts as replacement. Roberts is supposed to have said that now that he had muddied his hands by becoming a pirate, it would be better to be a commander of pirates than a common man.
Roberts proved to be one of the most feared pirates of the era. In a reign of sea terror lasting some two and a half years from 1719 to 1722, Roberts is believed to have captured 472 ships. He was so able an opponent that ship's captains surrendered immediately upon seeing his flags rather that fight.
Just months before his 40th birthday, he was reportedly killed off the coast of Africa in a battle with the HMS Swallow.under then Captain Chaloner Ogle. So feared was Roberts, that his defeat earned Ogle his spurs as a knight and put him on the fast track to becoming an admiral. Historians have marked Robert's death as the high water mark of the "Golden Age of Piracy."
Tall and dark, Roberts certainly served darkness, but defied the caricature of a blood-crazed lunatic. He preferred to be humane to his captives and sometimes gave them presents, not out of innate kindness, but because it served his purposes. A strict disciplinarian, he forbade women and boys on ship, preferred tea over hard liquor, did not smoke, and encouraged his men to abstain from alcohol and tobacco. Roberts also possessed both organizational ability and coolness under fire that earned him the respect of his enemies.
Roberts also had a great love for classical music and employed musicians to play aboard his ship whenever the crew wished, save for Sunday when he gave the musicians the day off.
He welcomed all nationalities into his crews except the Irish, who he simply could not trust. This aversion to the Irish was so well known that captured sailors would fake an Irish brogue in order to avoid being pressed into service aboard his vessels.
He was known to be a flashy dresser and dressed up not down for battle. On his last battle, he wore his trademark crimson clothes with a hat and red feather. Around his neck hung a gold chain and crucifix taken from a Portuguese treasure ship and intended for the King of Portugal. During the battle with the Swallow, his men said he was fatally wounded in the neck. He then told his men to throw him overboard rather than be captured. They supposedly weighted his body in chain, wrapped it in a sail then tossed overboard. The body was never recovered.
Above all, Roberts was a purposeful, talented, and rational leader who chose to serve evil, accepting the short life of a pirate because it offered him food and comfort over the grinding misery of a sailor's life. In that I find him understandable and at the same time unquestionably evil because he knowingly stepped over the line and accepted the consequences.