Emanuel Wynn

British Admiralty Records, in the Public Records Office in the UK show, in a report dated 18 July 1700, that HMS Poole, a 32-gun fifth-rate frigate[1] commanded by Captain John Cranby, engaged Wynn's ship off the Cape Verde islands.

Cranby enlisted the assistance of Portuguese soldiers, but thanks to their delay in attacking, Wynn slipped out of the harbor and escaped.

[2] Most historians agree that Cranby's journal is the first witness account of a black Jolly Roger used aboard ship,[3] which Cranby described as "a sable ensign with cross bones, a death's head, and an hour glass" (the quotation is from Earle, Pirate Wars, p. 154) or "A Sable Flag with a White Death's Head and Crossed Bones in the Fly.

[5] 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 their time was running out and only by timely surrender could they evade death.

[6] There were no other reports at the time of pirates using similar flags aboard ship (though red and other versions had been used by buccaneers during campaigns while ashore)[7] but within 15 years the skull and crossbones design and its many variants would become the standard flag of Golden Age pirates.