Captain Wynne

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Myth: Pirate: Captain Wynne. The first Pirate Little is known in the historic record of the fate of this pirate Captain but Emmanuel Wynne is often given credit for starting the "Jolly Roger" craze around 1700 with his skull and crossbones on a classic black background, accompanied by an hourglass image. The forerunner had been a white cross on a black flag. Wynne began his piratical career raiding English merchantmen off the coast of the Province of Carolina near the end of the 17th century. He later moved to the more profitable waters of the Caribbean attacking both English and Spanish ships. British Admiralty Records, dated 18 July 1700, report that the HMS Poole, commanded by Captain John Cranby, engaged Wynn's Pirate ship off the Cape Verde islands. Cranby chased Wynn into a cove at Brava Island but, assisted by Portuguese soldiers, Wynn escaped. Most historians agree that Cranby's account is the first mention of a Jolly Roger, which Cranby described as "a sable ensigne with cross bones, a death's head, and an hour glass." Wynne is believed to be the first pirate to fly the now familiar form of the "Jolly Roger." His flag, showing the distinctive skull and crossbones motif, was augmented with another common pirate symbol: an hourglass meant to signify to his prey that only by timely surrender could they evade death.
¾ inch diameter