Extremely little is known of Captain Wynn's life. Another of the first Captain's to use The Jolly Roger to identify himself as a Pirate, Wynn was known to have existed by virtue of his listing as a Pirate through British Admiralty reports of the 18th Century. He was known to operate in the Caribbean and off the Carolina's (America). HMS “Poole” (a British Warship) – reported engaging Wynn. Wynn and his crew escaped that fight. It was believed that Wynn was initially a Merchantmen (giving him intimate knowledge of the local sea trade routes). He and his crew were thought to have been killed in battle and his ship sunk by the British Navy in the 1720s.