Emanuel Wynne’s flag
A black flag with a white skull, crossed bones and an hourglass, reported in 1700 on the ship of the French pirate Emanuel Wynne. It is the earliest skull-and-crossbones pirate flag on record.
Meaning
British Admiralty records of 18 July 1700, as Guinness World Records summarises them, tell of HMS Poole under Captain John Cranby engaging Wynne’s ship off the Cape Verde Islands. Cranby chased him into a cove at Brava Island, but Wynne escaped with the help of Portuguese soldiers. Cranby described the flag as “a sable ensigne with cross bones, a death’s head, and an hour glass”. Guinness lists it as the first recorded Jolly Roger. Before it, Guinness notes, pirates flew red or black flags, red for no quarter and black for quarter, sometimes with a skull but usually plain.
Origin and history
The sources tell the 1700 fight with small differences. Charles Grey, who called it the first mention of the Jolly Roger in 1933, placed the action off St Jago (Santiago) in the Cape Verde Islands, as the World History Encyclopedia does; Guinness puts the chase at Brava. Grey and Guinness call Wynne French, the Encyclopedia a Breton. Grey’s is the oldest of the three accounts, and he quotes the description differently: “A Sable Flag with a White Death’s Head and Crossed Bones in the Fly”, with no hourglass, and he credits it to “Captain Poole”, taking the ship’s name for her captain’s. By 1710, Guinness says, most pirates flew flags of their own design.
How the form changed
Cranby listed the parts of the flag but not how they were arranged. The arrangement known today, a skull over crossed bones with the hourglass beneath, comes from the plate of pirate flags in Grey’s Pirates of the Eastern Seas (1933), drawn in black and white. Benerson Little notes that Grey’s flags, with their names, were copied exactly into Patrick Pringle’s Jolly Roger two decades later, and from there into later books.
Often confused with
The Jolly Roger in its later standard form is the skull and crossbones alone. The hourglass, a reminder that time is running out, is on several other flags of the period, among them Bartholomew Roberts’s Whydah flag and the one sold as Blackbeard’s.
Read next
- Next in Historical flagsVexillumThe vexillum was a Roman military flag: a square of cloth hung from a crossbar at the top of a spear. It was the standard of the maniples and of the cavalry, and its name came to cover any Roman standard except the legion’s eagle.
- The same shape in Celtic symbolsSt Brigid’s crossA small cross woven from rushes or straw on the eve of St Brigid’s Day, 1 February, and hung over the door or in the roof for the saint’s blessing and protection through the year. The four-armed form is the best known, but Irish crosses come in many shapes.
See also
Blackbeard’s flag, Jolly Roger, Calico Jack’s flag, Bartholomew Roberts’s flag, Aquila, SPQR.
Sources
- First "Jolly Roger" pirate flag, Guinness World Records, record entry 720049, Guinness World Records, record text
- Pirates of the Eastern Seas (1618-1723), A Lurid Page of History, Charles Grey, Pirates of the Eastern Seas (London: Sampson Low, Marston, 1933), Internet Archive full text, Internet Archive, The Black Flag, or the Jolly Roger, p. 17
- The Jolly Roger & Other Pirate Flags, Mark Cartwright, World History Encyclopedia, published 18 August 2021, World History Encyclopedia, The Jolly Roger
- The Fanciful, Mythical “Calico Jack Rackham” Pirate Flag, Benerson Little, Swordplay & Swashbucklers, 18 June 2021 (quoting his book The Golden Age of Piracy: The Truth Behind Pirate Myths, 2016), Benerson Little, quoting The Golden Age of Piracy
The same shape elsewhere
Browse symbols formed from crosses or squares and rectangles.
Researched, edited and approved by Rory Hansen before publishing. Last reviewed October 14, 2026. How we research
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