This is not a post I’d ever intended to write, believing–clearly foolishly–that publishing a book on pirate myths would once and for all send the the myth of Rackham’s pretended “skull and crossed swords” flag to perdition where it belongs. Or mostly so. How naive! It’s not just hope that springs eternal–so does myth flying in the face of contrary fact.

Although it’s well-documented that the “Rackham” flag–quite probably the most-depicted pirate flag in film–is a fanciful 20th century invention, Wikipedia via trolls and the ignorant continues to spew nonsense regarding both Rackham and this flag, the latest of which I learned, via a historical forum on Facebook, is that the two crossed swords might represent Anne Bonny & Mary Read. (For the record, all either of them did with a sword–quite possibly a machete, in fact, based on a witness statement–as pirates as far as we know is wave them at frightened merchant seamen who had already surrendered.) I’ll get to the ridiculous notion that the swords represent the women pirates in a moment.

Trying to correct Wikipedia is like playing Whack-a-Mole; it’s never-ending. Wikipedia is a prime resource for the lazy and the gullible, and trolls and others attempting to distort facts are well-aware of this. It’s one of the best places today to replace fact with nonsense, or worse. Don’t get me wrong: there are excellent articles on Wikipedia, including some on pirates and piracy. But to the uninitiated it can be hard to tell the difference between these and those that are little more than nonsense or outright propaganda. And even the best ones are often soon rewritten–and their important facts often disappear with the revision.

A few facts about Rackham & Co. before I describe the 20th century origin of the flag:

There is no record of any pirate flag John “Calico Jack” Rackham ever flew, if he even flew one. The only record of any flag he flew is of a white one, probably as a French flag for deception. This doesn’t mean he never flew a black flag, but if he did we have no idea what it looked like. None of the witnesses at his trial mention a black flag.

Again, as noted above, the black flag attributed to him, with skull (“death’s head”) and crossed cutlasses (or hangers or falchions) is a 20th century invention. More on this in a moment.

Rackham was a smalltime pirate who whose piracies prior to late 1720, if any (although likely; “Charles Johnson” claims he was once Charles Vane’s quartermaster), cannot be corroborated, and he would doubtless be entirely forgotten today were it not for two women who briefly sailed with him, Anne Bonny & Mary Read, and a publisher/editor, apparently Nathaniel Mist, who greatly “sexed up” their petty sea thieving. For most of his time in command, Rackham’s crew numbered only ten, including the two women and himself; he had added nine more drunk volunteers earlier the same day he was captured at sea. His piratical cruise lasted less than two months. It’s entirely likely that even his nickname, “Calico Jack,” is an invention: the moniker does not show up anywhere in the historical record except in Johnson’s book (and he invented many details in his book), unlike, for example, that of Edward Teach/Thache aka Blackbeard, which does show up regularly in the historical record.

At the time Rackham sailed with these women in his crew, he commanded a tiny 12-ton sloop named William he stole at anchor at New Providence (Johnson reimagined it as a swift 40 ton sloop), and was robbing small largely defenseless fishing and trading vessels in the waters off New Providence, Hispaniola, and Jamaica: seven small fishing boats, three merchant trading sloops, one small merchant schooner, and one small canoe. Most if not all of them were local “Mom & Pop” coastal seafarers, in other words. Hardly epic escapades. None of the vessels Rackham captured put up a fight.

Bonny & Read wore women’s clothing aboard, and dressed as men only the very few times they robbed small merchant traders and fishermen. In fact, there is only one confirmed attack in which they dressed as men, although it is probable they also did when capturing other vessels.

There was only one battle in which the two women pirates might actually have fought side by side–the battle in which they and Rackham were captured–and it was over in a moment, literally. There wasn’t much of a fight other than a single “great gun”–apparently in this case a swivel gun, not a carriage-mounted gun–and possibly a pistol fired by the pirates, and neither did any damage. There is no record of any other resistance by the two women pirates or any of the men. The pirates surrendered immediately after Jonathan Barnet’s sloop fired a broadside and volley of small arms. No pirates are recorded as having been wounded or killed in the brief action.

Further, most of what “Charles Johnson” wrote about Bonny & Read cannot be corroborated in spite of extensive research by numerous scholars and other researchers. Although much of what “Johnson” wrote about pirates in general is clearly factual and has been corroborated (pistols hanging from silk slings is an example of what might be invention proved to be a fact by the Whydah wreck, for example), he also embellished–lied–often, almost certainly to improve sales potential. His depiction of Bonny and Read as the only pirates willing to fight while the rest were drunk below deck, and Bonny’s scornful upbraiding of Rackham as having failed to fight like a man, were surely invented or grossly exaggerated by the author.

As for the modern origin of the flag, I’ll quote from the draft manuscript of The Golden Age of Piracy: The Truth Behind Pirate Myths (I’m too lazy to pull up the published final):

“Many…pirate flags depicted today, such as those purportedly of  Stede Bonnet, Calico Jack Rackam, and Blackbeard, are modern inventions without historical basis. The pirate flag we know incorrectly as Calico Jack’s, with crossed cutlasses under a skull, may well have been inspired by the flag used in the 1935 film version of Captain Blood, that of a pair of cutlass-holding arms crossed beneath a skull. And this film flag may have been inspired by the early flag of Bartholomew Roberts, that of a death’s head and an arm holding a cutlass, or by the Dutch red battle ensign with an arm holding a cutlass, or by the seventeenth century flag of Algiers (a notorious have of Barbary corsairs), or even by a Barbary corsair flag of no quarter.

“We simply do not know what the pirate flags of these three pirate captains really looked like…except that Blackbeard’s was a black flag with a “death’s head,” and not the commonly attributed black flag with horned skeleton [apparently a very early 20th century invention]. Similarly, the purported pirate flags of Christopher Moody and John Quelch are misattributions: Moody’s is actually the Barbary corsair flag of no quarter described later in this chapter, and Quelch never flew a pirate flag…

“The origin of our modern popular but fanciful renditions is a series of several books whose illustrations were passed from one to the next, with few or any changes. The earliest publication of this series discovered to date—and probably the origin [except for the fanciful Blackbeard horned devil flag which was published previously in The Mariner’s Mirror]—is Basil Lubbock’s The Blackwall Frigates, published in 1922. The book includes a plate of eight pirate flags (even though the Blackwall frigates only came into being a century after the Golden Age of Piracy expired, but pirate flags sell books), three of which are misattributions, although otherwise mostly accurate, and one is a fanciful flag taken from an illustration in Charles Johnson’s pirate chronicle. [Rackham’s purported flag is not among them.]

“Most of these flags, with names now added, were reproduced in Charles Grey’s Pirates of the Eastern Seas. Patrick Pringle’s Jolly Roger: The Story of the Great Age of Piracy, published two decades later, includes nine pirate flags, all reproduced exactly from Grey’s book. In 1959, Hans Leip’s Bordbuch des Satans (Log of the Satans) includes some very similar flags clearly inspired by Lubbock, Grey, and Pringle, although two have been miscaptioned. Leip also adds three new flags, all imaginary: those of Calico Jack Rackam, Stede Bonnet, and Henry Every [“Long Ben”]. [Every’s flag includes a skull with a bandana and earring, a clear giveaway that it’s an invention.]

“Most of Leip’s pirate flags were reproduced exactly in 1961 in Pirates of the Spanish Main, part of the American Heritage Junior Library, with credit to Leip’s book. Pirates of the Spanish Main became a classic source of historical pirate lore—and mythical pirate flags—to literally thousands of young readers who imagined themselves pirates, not to mention to publishers of subsequent books on piracy. Similarly identified flags, some accurate, some, like those in the other books, not, were published in 1978 in Pirates, a title in the popular Time-Life “The Seafarers” series [including the “Calico Jack” flag with crossed swords]. It is no surprise that inaccurate images of pirate flags would appear in pirate books: for many publishers, the main purpose of images in a book is to get readers to buy it. The image of the “Jolly Roger,” whether accurate or not, is the perfect lure.”

The two most similar written descriptions of historical black pirate flags circa 1715 to 1730 to Rackam’s purported flag are “this flag was a black cloth in the middle of which was depicted a cadaver [skeleton] and scattered bones and crossed sabers” (I’ve translated this from French), and “The Ship hoisted a Black Flagg at the Main-Top-Mast-Head, with Deaths Head and a Cutlass in it…” Neither were hoisted by Rackham. The former is the only reference I’ve found to crossed swords among the many eyewitness descriptions of pirate flags.

If there were an early 18th century origin to the Rackham flag, we can blame Daniel Defoe’s Captain Singleton, a pirate novel published in 1720: Captain Bob [Singleton] flew “a black flag, with two cross daggers in it.” We cannot be certain this is the ultimate origin, for the idea of crossed swords is quite common throughout history.

Soon after I posted this blog, my friend Antón Viejo Alonso mentioned to me that conquistador, traitor, sociopath, and murderer Lope de Aguirre is said to have had three identical flags made in 1561, each with a black field with red crossed swords, the colors representing the blood he shed and the “lamentations and mourning” he caused. Whether this may have influenced Leip’s illustrator is unknown. Many flag designs appear to be parallel developments independent of previous or current similar flags, and not descendant, although clearly many also fall into the latter category. Black flags, and mortuary symbols on flags, have been around since antiquity, and have been used on land as well as sea. Aguirre’s flags were described by Friar Pedro Simón (1574 – circa 1628). The English translation of his work is entitled The Expedition of Pedro de Ursúa & Lope de Aguirre in Search of El Dorado and Omagua in 1560-1 (London: Hakluyt Society, 1861). A modern reprint is also available.

The modern “Calico Jack” flag of skull and crossed swords is a popular one in pirate films and among pirate fans. I myself own versions in both black and red, but I don’t represent them to be authentic. It’s an easy flag to imagine, substituting crossbones for crossed swords. I can even imagine myself creating it today or three centuries ago, or even today, given my interest in piracy and swordplay.

The “Calico Jack” flag has been used in several films, and a possible, even likely inspiration for its use in pirate movies, including the Disney franchise, is the flag flown aboard the pirate ship Wicked Wench in the Pirates of the Caribbean attraction at the Disneyland theme park. In fact, the design is also used early on in the ride in the form of a talking skull, with crossed cutlasses beneath it, providing safety and other information to visitors.

Very likely, the ride’s designers selected the design from the book The Pirates of the Spanish Main (1961) discussed above, although it is possible the Captain Blood film flag was also part of the inspiration. In fact, the entire ship-attacking-fort scene in the attraction was copied from the similar scene in the film. Notably, the attacking Spanish ship in the novel the film was based upon is described as red-sided, just as is the Wicked Wench in the attraction. (Carrying the hypothesis further, is the name Wicked Wench a bit of a joke on the Arabella–the name of Captain Blood’s ship–and the very proper English lady whose name it was? This would be in keeping with the piratical sense of humor of the attraction’s designers.)

All of this suggests that the Wicked Wench was the first fictional, and for that matter, non-fictional as well, ship to fly the “Calico Jack” Jolly Roger–although arguably the Arabella of the film Captain Blood did so in its original form. It’s entirely possible therefore that all subsequent film pirate ships flying the flag may have been inspired in part by the flag flown by the Wicked Wench, which was in turn inspired by the book The Pirates of the Spanish Main, and ultimately by the film.

(Historical note: buccaneer ships, one of which the Wicked Wench was originally depicted as, rather than as the pirate ship which would become the Black Pearl, did not fly black flags with skull and bones–only those of later pirates did.)

In Swashbuckler (1976), a version of the flag with ensanguined cutlasses is shown flying at the masthead of the Blarney Cock in the film, and flying in a odd arrangement at its stern in the movie poster and other marketing materials. The film stars Robert Shaw, Genevieve Bujold, James Earl Jones, Peter Boyle, Beau Bridges, Geoffrey Holder, Avery Schreiber, and, in an early role, Angelica Huston:

Captain Thomas Bartholomew Red (Walter Matthau) flew a version in Pirates! (1986) aboard the captured Spanish galleon Neptune:

Morgan Adams flew it aboard the Morning Star in Cutthroat Island (1995); “Hoist the colors!” she orders at the beginning of the battle with Dog Brown’s Reaper. The flag flown from the Morning Star was slightly modified from the original 20th century illustration, although the popular “original” was used on posters and other promotional materials. The film, although it bombed at the box office (odd that a blockbuster is a film that makes lots of money, yet a blockbuster is also a very large bomb…), has a great soundtrack, plenty of comic book pirate action, and Geena Davis did a better job portraying a pirate captain than many men have in films.

It was flown aboard the Black Pearl in Pirates of the Caribbean: The Curse of the Black Pearl (2003) at the beginning of the film when Elizabeth Swann imagines she sees the ship in the distance as she holds up a cursed Aztec coin, probably because this was the flag originally flown aboard the Wicked Wench, which was via a certain revisionism converted from a buccaneer ship to the former name of the Black Pearl.

It was flown again aboard the Black Pearl it in Pirates of the Caribbean: At World’s End (2007) during the “Hoist the colors!” scene–again, a badass female pirate gives the order–and in the engagement following:

The “Calico Jack” skull and crossed swords also appears in Pirates of the Caribbean: Dead Men Tell No Tales (2017) on the main-topsail of the Queen Anne’s Revenge, now commanded by Capt. Barbossa. The sails are of wine red or burgundy velvet with yellow-gold tassels, probably an homage to or inspired by the reputed sails of some the wealthiest Cilician pirates in antiquity. Some even captured Julius Caesar, who, after ransoming himself, had the pirates captured and put to death.

That said, author George MacDonald Fraser in his comic novel The Pyrates (1984 US edition) described the sails of the Grenouille Frénétique (the Frantic Frog), commanded by Happy Dan Pew, as having “velvet sails…fringed with silk tassels in frightful taste…” In fact, Barbossa’s “bon vivant and gourmet” image in Dead Men Tell No Tales might well have been inspired by Fraser’s description of Happy Dan Pew.

The iconic flag was also used in Peter Pan (2003) as both a traditional Jolly Roger and as a sail decoration, notwithstanding that sail decoration, with the exception of an occasional Spanish fishing vessel and similar, had for more than half a century been abandoned by the late 17th and early 18th centuries which provided the piratical source material for Mr. Barrie and Peter Pan (or Peter and Wendy if you prefer).

The “Calico Jack” flag is depicted also in the Starz Black Sails series at the very end of the final season. I was the historical consultant for all four seasons, and for reasons of both history and legal liability I traced the origin of the purported Calico Jack flag for the producers. The writers wanted to use the flag because it was already popularly attributed to Rackham, the set designers wanted something that looked authentic, and the lawyers wanted to be sure there was no copyright or trademark infringement.

A version was used in Lego Scooby-Doo! Blowout Beach Bash (Warner Bros., 2017). Scooby-Doo has always been fond of pirates, or at least ghost pirates and fake pirates…

Such an icon is the flag that it shows up in modified but immediately recognizable form, here in the BBC’s Doctor Who episode, “Legend of the Sea Devils” (2022):

Navy SEALs sometimes wear a “Calico Jack” flag patch on their field uniforms. Often the flag’s skull has an eye patch, a variant based most probably on choice of vendor. If my memory is correct–for the record, I’m a former Navy SEAL–its use began in the very late 80s when “real world” VBSS operations (board and search operations) were put to use. I might be mistaken, however. Pirate flag patches weren’t yet a fad in the Teams I served in (ST-3, SDVT-1) in the 80s. Certainly the “Calico Jack” patch remains in use today by Navy SEALs. Luminox, maker of a watch used by Navy SEALs, even has, or had, a special limited edition (375 watches only, I think) Navy SEAL watch with a Rackam skull and crossed swords on its face, although notably not the most common design of the flag, at least on one version. (See below, I couldn’t get captions to work on the tiled images.) Other military special operations units have been spotted wearing the flag patch, or one similar, too.

[Self-Promotion Alert!] The “Calico Jack” flag is also on the cover of The Golden Age of Piracy. Again for the record, the publisher chose the cover. I had no real input, although I’ve no problem with it. It certainly stands out and gets attention, and that’s what dust jackets are supposed to do. It slipped my mind when I first drafted this blog post that the Polish edition also uses the “Calico Jack” flag. (Sorry, Maciej Studencki, for missing this the first time around!)

If you’re looking for more details on pirate flags–accurate details, that is–you can read the book above or Ed Fox’s Jolly Rogers, the True History of Pirate Flags (author given as E. T. Fox). Or better yet, both. 🙂

If you’re looking to fly the flag, try eBay, lots of vendors carry it. It’s also available in red, and in design variations as well. There’s also a “weathered” version in red, but I’ve only seen it available so far at one ebay vendor and a few non-eBay vendors. Plus there are patches, stickers, T-shirts, rings, cufflinks, and more. If you want to fly the flag regularly, plan to pay a little more for sturdier nylon and construction; in particular, look for fabric that’s fade-resistant (all flags fade eventually). If you want to make your own authentically, you’ll need wool bunting or, in a pinch, silk.

When buying, remember, black means “good quarter if you surrender now,” which in practice means “surrender now and we might not murder, torture, or abuse you much,” and red means “no quarter, we’re going to kill you all.” Perhaps the best description of the meaning of the red flag of no quarter comes not from my books, or any other book on piracy, but from Les Aventures de Tintin: Le Secret de la Licorne (Casterman, 1946; reprints in many languages; in English, The Secret of the Unicorn). Enjoy! Don’t read French? “Tonnerre de tonnerre de Brest!” It’s never too late to start learning another language! Or, buy the English version. It’s a fun read, and there’s a sequel too.

Copyright Benerson Little 2021-2022. First posted June 18, 2021. Last updated February 5, 2023.