First "Jolly Roger" pirate flag

Pirates have used flags to identify themselves for hundreds of years. During the 17th century, they flew either red or black flags: red meant they would provide “no quarter” (i.e., no mercy) while black meant they would give quarter. Sometimes the flags had a skull, but usually they were just plain colours. The first recorded use of the now-iconic “Jolly Roger” known as the black flag featuring a skull and crossbones, was that of the French pirate Emmanuel (Emanuel) Wynne (Wynn), who flew it during a battle in July 1700.

British Admiralty Records dated to 18 July 1700 tell of HMS Poole, commanded by Captain John Cranby, engaging Wynne's ship off the Cape Verde Islands in the Atlantic Ocean. Cranby chased Wynn into a cove at Brava Island but, with help from Portuguese soldiers, Wynne escaped. Cranby described Wynne's flag as "a sable ensigne with cross bones, a death's head, and an hour glass."

By 1710, most pirates flew their own flags with their own personalized designs.