Wynne is one of the first pirates to fly a Jolly Roger as we know it today. His flag consisted of a white skull over crossed bones with an hourglass underneath. This was a symbol to anyone who saw it that time was running out and that they could only avoid death by surrendering.
One of the few contemporary descriptions of Wynn’s flag comes from Captain John Cranby, who commanded the HMS Poole. The Poole attacked Wynn off the Cape Verde islands in July of 1700. Cranby’s description is as follows: “a sable ensign with cross bones, a death’s head, and an hour glass.”
Following the attack by the Poole, Wynn left the Cape Verde islands for the Caribbean and more profitable raiding opportunities, attacking British and Spanish shipping. His eventual fate is unknown.