The Jolly Roger is the only flag in this encyclopedia designed to make you surrender. National flags claim territory; the pirate's black flag made an offer. Run up in the last minutes of a chase, it told a merchant crew exactly who was closing on them and laid out the deal: strike your colors now and live, or resist and meet the other flag, the red one. It worked often enough that most pirate captures involved no fighting at all. And despite three centuries of fiction flattening it into one skull-and-crossbones design, the historical Jolly Roger was a genre, a shared vocabulary of death that every captain arranged his own way.
Terror as a business model
Piracy in the Golden Age, roughly the 1690s to the 1720s, was a numbers business. A pirate crew might be a hundred strong against a merchantman crewed by a dozen, but boarding actions killed pirates too, and cannon fire wrecked the cargo everyone was there to steal. The ideal capture was a surrender, and the flag was the instrument that produced surrenders. A ship that hauled up a black flag with a death's head was declaring itself outside all nations and all rules, which was precisely the point: the terror was calculated, and heavily advertised.
The system had two settings. The black flag signaled that quarter would be given on surrender. The red flag, the older "bloody flag" borrowed from 17th-century naval usage, meant no quarter. Crews that resisted past the raising of the red flag could expect no mercy, and pirates cultivated that reputation because it made the next capture cheaper. Flying the black flag was also legally fatal: in Admiralty courts, the flag itself was evidence of piracy, and captured flags were paraded at trials and executions.
The death's head appears
The earliest firmly documented Jolly Roger dates to about 1700, when Captain John Cranby of HMS Poole engaged the French pirate Emanuel Wynn off the Cape Verde Islands and logged his ensign: a black flag with a death's head, crossed bones and an hourglass. Nothing in the design needed inventing. Skulls, bones, hourglasses, skeletons and darts were the stock memento mori imagery of the period, carved on gravestones across Europe and the American colonies, and printed in mourning ephemera. The pirates' innovation was to aim the reminder of mortality at other people.
Over the following two decades the vocabulary spread through the Atlantic and Caribbean pirate community, which was small, interconnected and imitative. By the 1710s and early 1720s, the black flag was standard equipment, and observers recorded a whole bestiary of variants: full skeletons, spears piercing hearts, hourglasses held aloft, cutlasses in hand.
Named flags of named pirates
A few designs are documented well enough to attach to specific captains. The best is Bartholomew Roberts's, and it is also the most personal. After the governors of Barbados and Martinique sent ships to hunt him, Roberts had a flag made showing a large figure of himself, sword in hand, standing on two skulls labeled ABH and AMH: A Barbadian's Head and A Martinican's Head. It was less a symbol of death in general than a public death threat against two named islands, and Roberts flew it until the Royal Navy killed him in battle in 1722. Contemporary accounts also describe a second Roberts flag, showing him standing with a skeleton.
Edward Low, among the cruelest captains of the era, flew a red skeleton on a black field, first recorded in 1723. Francis Spriggs, who had sailed with Low, flew a similar design and called it by the same name, which is part of how we know "Jolly Roger" was generic: Johnson's General History notes Roberts's crew in 1721 and Spriggs's in 1723 using the name for flags that looked nothing alike.
Then there are the famous flags that history cannot back up. The horned skeleton toasting the devil attributed to Blackbeard appears in no period source, and the attribution seems to be a 20th-century invention; period witnesses describe him under black flags with death's-head imagery, without that design. Calico Jack Rackham's skull over crossed cutlasses has the same problem. The most reproduced "historical" pirate flags are, in large part, modern folklore.
Old Roger, Joli Rouge and the etymology problem
The name is first printed in the 1720s and explained by nobody at the time. A 1723 newspaper account has pirates calling their flag "Old Roger," an established nickname for the devil, which makes "Jolly Roger" a plausible ironic upgrade. The widely repeated theory that the name anglicizes "joli rouge," French for the pretty red flag, has a satisfying logic and no period evidence whatsoever; historians generally discount it. A third suggestion, linking the name to "King Roger" of Sicily, has even less. The honest answer is that pirates named their flag after the devil or after nothing recoverable, and the name outlived every ship that flew it.
From pirates to periscopes
The flag's working life ended with the mass trials and hangings of the 1720s, but its second career began with an insult. In 1901 Admiral Sir Arthur Wilson, contemplating the Royal Navy's first submarines, called them "underhand, unfair and damned un-English" and suggested captured submarine crews be hanged as pirates. Thirteen years later, in September 1914, Lieutenant Commander Max Horton's HMS E9 torpedoed the German cruiser Hela, the Royal Navy's first submarine kill of the war, and Horton entered Harwich flying a homemade Jolly Roger: message received, admiral.
The gesture became a tradition. In the Second World War, Royal Navy submarines returning from successful patrols flew Jolly Rogers embroidered with a private code of symbols: bars for ships sunk, daggers for special operations, stars for gun actions. The practice survived into the missile age. HMS Conqueror flew the Jolly Roger returning from the Falklands War in 1982, after sinking the General Belgrano, and British submarines have flown it after operations since. A flag invented to advertise lawlessness is now hoisted, with official tolerance, by commissioned warships of the crown that used to hang its owners.
References
[1] "Jolly Roger," Wikipedia, covering the etymology theories, Emanuel Wynn, and documented captain's variants. https://en.wikipedia.org/wiki/Jolly_Roger
[2] Johnson, Charles. A General History of the Robberies and Murders of the Most Notorious Pyrates (1724), the primary published source for Roberts's, Low's and Spriggs's flags.
[3] Rediker, Marcus. Villains of All Nations: Atlantic Pirates in the Golden Age (2004). Beacon Press. On the social world and symbolism of Golden Age piracy.
[4] "Use of the Jolly Roger by submarines," Wikipedia, on Wilson's 1901 remark, HMS E9 in 1914 and the Royal Navy tradition. https://en.wikipedia.org/wiki/Use_of_the_Jolly_Roger_by_submarines
[5] Royal Navy Submarine Museum, Gosport, collection of submarine Jolly Rogers including First World War examples. https://www.nmrn.org.uk/