The Generation of the Jolly Roger

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

Two previous generations of piracy’s Golden Age used varied standards and colors for identification. The fabled West Indies Buccaneers of the 1670s and 1680s, commanded by men like Sir Henry Morgan and Captain Bartholomew Sharpe, flew national standards or their own banners, and were filled with the radical zeal of Protestants fighting against the New World empire of Catholic Spain. During Captain Sharpe’s attack on Spanish-held Darien in 1680, his Buccaneer companies flew flags of solid red, solid green, red with white and green ribbons, red with yellow stripes, and a red and yellow striped ensign with a hand holding a sword for the device.⁵ The next generation, the pirates of the 1690s who mostly used Madagascar as a base to attack shipping between India and Arabia, assumed the quasi-legal appellation of “privateer,” ostensibly dividing any prize profits with their backer. Captains William Kidd, Henry Avery, and Thomas Tew flew national standards, like the famous English Red Ensign, but also flew other national flags as a ruse de guerre to surprise their quarry. They developed a language of battle flags widely used among privateers when approaching a prize. As would continue to be the case, flying a black flag meant surrender immediately or engage in battle. Flying a red flag meant that no mercy would be given. Captain Thomas Pound ordered a “bloodie flag” hoisted when he cruised off Massachusetts in 1690. Captain John Halsey flew a red flag from the main masthead of his ship when he chased the Essex off the coast of East Africa in August 1708. In the maritime world, correctly interpreting the meaning of flags and their devices meant life or death, and word quickly spread among mariners of all nationalities.⁶

The final generation of pirates began when a large number of sailors, left unemployed after the conclusion of Queen Anne’s War, began striking out from their base of Providence Island in the Bahamas in 1716. This third and most desperate generation of pirates identified not with any country or king, though most were English, but with their own communal sovereignty, and attacked ships of all nations. They charged their black and bloody flags with images of fighting, of time, and of mortality, borrowing freely from gravestone carvings, printed sources, and the mark of a crewman’s death in a ship’s log. An estimated 2,400 sailors turned pirate, and their cruelty in seizing prize ships led to them being hunted down, tried, and executed. This was the “Generation of the Jolly Roger,” and of the most famous pirates in history.⁷

The Jolly Roger was seen on pirate ships sometimes as a plain black flag, but the more successful a pirate became, the more brazen his attacks and the more explicit and visually defiant his flag. Captain John Martel in 1716 flew “a Jack, Ensign and Pendent, in which was the figure of a Man, with a Sword in his Hand, and an Hour Glass before him, with a Death’s Head and Bones. In the Jack and Pendant were only the Head and Cross-Bones.”⁸ The pattern was established and others followed. Captain Richard Worley flew a black ensign with a white death’s head in 1718, as did Edward England in 1720. Stede Bonnet in 1718 added a dagger and heart to his flag, while Calico Jack Rackham, sailing with the female pirates Anne Bonney and Mary Read, used crossed swords instead of bones. Edward Teach, better known as Blackbeard, flew a black flag with a white horned skeleton holding a dart pointing to a red heart dripping three drops 
of blood when he terrorized the Carolina coast in 1718. Captain Ned Low, a particularly vicious pirate, assumed the title of “Admiral” in 1723 and hoisted a black flag with a skeletal figure of death in red. Captains Howell Davis, Oliver LaBouche, and Thomas Cocklyn greeted one another as brothers on seeing each other raise their black flags. The most successful pirate of the age, Captain Bartholomew Roberts, who scored hundreds of prizes around the entire Atlantic world in the early 1720s, sailed under four of the most unique examples of the Jolly Roger: a “Death’s Head and Cutlash (cutlass);” a “Death (white skeleton) ... with an Hour Glass in one Hand, and Cross-Bones in the other, a Dart by it, and underneath a Heart dropping three Drops of Blood;” a “New Jack ... with his own [Roberts’s] Figure portray’d, standing upon two Skulls, and under them the Letters ABH and AMH signifying a Barbadian’s and a Martinican’s Head” (for his intense hatred of the governors of Barbados and Martinique); and finally, a skeleton and the figure of Roberts holding aloft either an hourglass or a drinking glass in a toast. When Roberts was finally killed in battle with the Royal Navy off the coast of Africa, his crewmen threw the flags overboard, so they could not “be display’d in Triumph over them.” Within a few years after the defeat of Roberts, the last of the pirate crews were hunted down, tried, and executed, ending the Golden Age of Piracy. The Jolly Roger was the symbol of this last generation’s defiance of authority, time, and death. It was the symbol of their allegiance to no other but themselves and of their own Atlantic-borne sovereignty.