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Pirate Emanuel Wynn used a flag with skull, crossbones and hourglass as early as 1700, the first one known to do so. This is verified from reports of John Cranby, captain of the British ship HMS Poole, now archived at the London Public Record Office.
Emanuel Wynn (or Wynne) was a French pirate, the first one identified as having flown the black and white Jolly Roger. His flag had an hourglass beneath a set of bones, indicating that time was running out for anyone that didn’t simply surrender. He began his pirate career around in the late 1600s, preying on British merchant ships off the Carolina coast of North America. Later he moved on to the West Indies, taking both British and Spanish plunder.
British records state that on the 18th of July in 1700, Wynn was off the coast of the Cape Verde Islands when it was challenged by the Royal Navy vessel HMS Poole, Captain John Cranby commanding. Cranby pursued Wynn and his ship into a cove at Brava Island, but the local Portuguese helped Wynn and he escaped.
Cranby’s log described Wynn’s flag, which is generally believed to be the first recorded use of a Jolly Roger flag. The flag of Wynn was described by Cranby as a black flag with “…cross bones, a death’s head, and an hour glass.”
Both the hourglass and the crossed bones became common symbols of pirates. Sometimes swords replaced the bones, and other symbols appeared on the flag, but the basic design became well-known.