Place  /  Origin Story

The Generation of the Jolly Roger

26 pirates were put to death in Rhode Island on July 19, 1723. Their flag, and everything it stood for, hung with them.
New York Public Library

Gravelly Point in Newport Harbor, Rhode Island, witnessed the gruesome spectacle of a mass hanging just after noon on 19 July 1723. Twenty-six men, the youngest just seventeen and the oldest forty years of age, were hanged for the crime of piracy. Captain Charles Harris, a 25-year-old London native, was hanged alongside his crew before a crowd of thousands gathered on shore and in boats. The pirates were not alone in hanging from the gallows. A flag, the most potent and illustrative symbol of their criminal way of life, was hung with them:

Their Black Flag, with the Pourtrature of Death having an Hour-Glass in one Hand, and a Dart in the other, at the end of which was the Form of a Heart with three Drops of Blood, falling from it, was affix’d at one Corner of the Gallows. This Flag they call’d Old Roger, and often used to say they would live and die under it.1

Although the iconography may not be the typical white skull and crossed bones on a black field, this flag which Harris and pirate crew called “Old Roger” was indeed a variant of the most recognizable maritime flag in history—the Jolly Roger, the acknowledged standard of the Golden Age of Piracy’s third and final generation.2

What colonial Rhode Island’s provincial authorities were demonstrating by hanging the Jolly Roger on the scaffold with the corpses was the two-fold forcefulness of the flag. Black flags of canvas or silk communicated a visual message (surrender peacefully or face battle) to potential prize ships at sea. The pirates’ black flags also served as the representative symbol of those men who “went on the account,” (as turning pirate was called) in the eyes of both national authorities (the crown, provincial governors, admiralty courts) and also in the eyes of the pirates themselves. Various pirate flags incorporated “a triad of interlocking symbols—death, violence, limited time,”3 aspects of maritime life with which all sailors, especially pirates, were intimately familiar. Depending on the particular crew and captain, the flag was usually black and emblazoned with devices, sometimes the famous skull and crossed bones of a death’s head, a full skeleton or “anatomy,” crossed swords, hourglasses, darts, hearts dripping blood, or even an image of the pirate captain himself. It is surprising to realize that it was only during the last ten-year period of piracy’s Golden Age, from 1716 to 1726, that the Jolly Roger assumed its most documented, familiar form, and its undisputed prominence as the flag of pirates throughout the Atlantic world.4