🏴‍☠️ Pirate Flags — The Untold Story The first documented black pirate flag appeared in 1700. It was flown by Emmanuel Wynn — a black flag with a death’s head. (Yes… we put it in the video.) Before that moment, many pirates flew red flags. Red meant one thing: No mercy. And this may be where the name Jolly Roger truly comes from — not a cartoon skeleton, but the French phrase joli rouge — “pretty red.” But here’s the part Hollywood gets wrong. Pirates did not want to kill or destroy ships or ca