A pirate crew raising a flag was not decoration. It was a threat delivered at a distance, timed to a merchant captain’s decision about whether to fight or surrender before the range closed enough for cannon fire to matter. The flags pirates flew, and the order in which they flew them, were a calculated part of how piracy actually worked.
Where the Name “Jolly Roger” Came From
Nobody has settled where the name originated, and the honest answer is that at least two explanations have real evidence behind them. One traces it to “Old Roger,” a period nickname for the devil, which fits the skeletons and death imagery pirates favored. The other derives it from the French joli rouge, “pretty red,” a reference to the plain red flags flown by privateers and, later, pirates. The term itself is first recorded in the early 1720s, used by men sailing with Bartholomew Roberts and Francis Spriggs, well after black-and-white death flags were already in use. So the name arrived after the custom, not before it.
Black Meant Surrender, Red Meant No Quarter
The two-flag system is the part most retellings get backwards or drop entirely. A black flag was the opening move: it told a merchant crew that if they struck their colors and surrendered without a fight, they would likely be robbed but not killed. One captain’s own account from 1719 described the black flag’s purpose plainly, as intended to frighten honest merchantmen into surrendering “on penalty of being murdered if they do not.” A red flag was the escalation. If the target crew resisted, or simply took too long to decide, the pirates would run up red instead of or alongside the black, signaling that no quarter would be given at all. Red flags predate the pirate era; English privateers had used red ensigns for similar reasons, and pirates inherited both the object and the threat it carried.
The First Skull and Crossbones
The design most people now picture, a white skull over crossed bones on black cloth, is usually traced to the French pirate Emanuel Wynne, recorded flying a black flag with a skull, crossbones, and hourglass off Santiago around 1700. It was not standardized for another two decades. Through the 1710s and 1720s, as Golden Age piracy peaked and then collapsed, individual captains designed their own variations, and a merchant crew who recognized a particular flag might already know, by reputation, what kind of captain they were dealing with.
Every Captain Had His Own Design
Blackbeard’s flag, by most surviving descriptions, showed a skeleton spearing a bleeding heart while holding an hourglass, a fairly literal message about time running out. Bartholomew Roberts flew more than one design over his career, including a figure of himself standing on two skulls, separately labeled with initials aimed at the governors of Barbados and Martinique, a direct threat tied to two colonial administrations that had specifically targeted his crews. Edward Low’s flag reportedly showed a red skeleton on black, dispensing with the surrender option’s usual black background entirely. Stede Bonnet’s flag paired a skull with a heart and a dagger. These were not interchangeable; a captain’s flag functioned as a kind of signature, and its imagery often responded to a specific grievance or reputation the captain wanted to project.
Why the Flags Worked as Well as Weapons
A merchant vessel that surrendered on sight cost pirates nothing: no gunpowder spent, no rigging damaged, no crew wounded in a fight over cargo the pirates wanted intact anyway. The flag system’s entire logic was to make capitulation the safer choice before a shot was fired. That is also why the flags leaned on the imagery of mortality familiar from gravestones and mourning art of the period, skeletons, hourglasses, bleeding hearts, rather than more abstract or purely decorative symbols. The image needed to be legible and alarming from a moving ship’s deck in a matter of seconds.
Sources consulted: Royal Museums Greenwich, National Maritime Museum (“Pirate flags decoded”); World History Encyclopedia (“The Jolly Roger & Other Pirate Flags”); Charles Johnson, A General History of the Pyrates (1724).
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