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The Fanciful, Mythical “Calico Jack Rackham” Pirate Flag

The popular fanciful “Calico Jack” Jolly Roger.

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 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 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.) But I’ll get to this ridiculous notion 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. And even the best ones are often soon rewritten–and their important facts often disappear with the revision.

John “Calico Jack” Rackam (or Rackam) as depicted in an early edition of Charles Johnson’s pirate history (1726). The image is entirely fanciful, it is certainly not an eyewitness image.

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 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 possible that even his nickname, “Calico Jack,” is an invention.
  • 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. There was only one battle they might actually have fought in together–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. Although much of what “Johnson” wrote 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.
The pirate flag from Captain Blood (1935) starring Errol Flynn. This flag is a possible inspiration for the “Calico Jack” flag: crossed arms with swords instead of crossed swords, and the sword hilts are virtually identical to those of the “Calico Jack.” The color of the flag in the film is unknown, but I’d like to think it’s red as a “no quarter” banner which would be somewhat historically accurate. DVD screen capture.

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. 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, 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.]

The “Jolly Rogers” depicted in The Blackwall Frigates, 1922. The “Calico Jack” flag is absent. I’ve no idea where the idea of a pirate pendant stiffened with battens came from; it’s not in the written piratical record anywhere.

“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.]

The pirate flags in Hans Leip’s Bordbuch des Satans (Log of the Satans), 1959. This is the first apparent appearance of the “Calico Jack” flag with crossed swords. Author’s library.

“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 front cover of Pirates of the Spanish Main, part of the American Heritage Junior Library, 1961. This book inspired numerous young pirates and provided them with numerous iconic images. Author’s library.
Pirates of the Spanish Main in the attic scene in The Goonies (1985). Blu-ray screen capture.
The pirate flags depicted in Pirates of the Spanish Main, 1961. The are copies of those in Leip’s book. Author’s library.

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.

Soon after I posted this blog, my friend Antón Viejo Alonso mentioned to me that conquistador 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).

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, given my interest in piracy and swordplay, not to mention, in a modern sense, its associations with Navy SEALs and Cutthroat Island (see below).

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.

Cutthroat Island Blu-ray screen captures.
The “Calico Jack” flag was also used on the teaser poster and other promotional materials.

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:

Blu-ray screen captures.

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 bad ass female pirate gives the order–and in the engagement following:

Blu-ray screen captures.

The “Calico Jack” flag is 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.

Black Sails Season 4 Blu-ray screen capture.
The Calico Jack Rackham flag as designed by the Black Sails production crew and sent to me for comment. Hopefully the Starz lawyers won’t mind me posting this. 🙂

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 units wear the flag patch too.

US Navy SEALs (reportedly: I haven’t confirmed the image) sporting the Calico Jack Rackham flag, apparently after fast-roping onto a vessel for a photo op.

[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!)

The Polish edition, translated by Maciej Studencki.

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 at 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. First posted June 18, 2021. Last updated July 30, 2021.

Hollywood Boarding Actions: “Alright, My Hearties, Follow Me!”

An English privateer coming alongside a Spanish galleass in The Sea Hawk (Warner Bros., 1940) starring Errol Flynn. The scene was shot in an indoor set, with partial replica ships–sets, that is–sitting in a water tank. The ships were moved together on rails hidden underwater. Author’s collection.

We may have only seen the ship-to-ship action coming alongside “board and board” in but a single film, and certainly in no more than two or three, but the Hollywood image of “Boarders away!” is indelibly impressed on our swashbuckling psyches.

I’m not going to go into the details of coming alongside, nor many of the actual boarding action afterward, which in Hollywood films the latter is usually composed of “cutlass-sharpening hack-and-slash” action. Plus, I’m lazy, or rather, in a hurry to complete longer more detailed blog posts, making this one a bit of a placeholder as I finish the remaining three “Duel on the Beach” posts. For more detail on how boarding actions actually happened, see The Sea Rover’s Practice (and also the associated pdf of additional information and comments).

A boarding action with ships pretty much equally “board and board” in The Son of Captain Blood (Paramount, 1963) starring Sean Flynn, son of Errol Flynn. The scene arrangement may be an homage to the similar scene in The Sea Hawk or simply a convenient way to shoot it. Author’s collection.

I will note the two most outstanding parts of the image. First, for reasons of simplifying the image for audience, not to mention of shooting it and for the powerful graphic image it makes, Hollywood usually shoots the scene in only one fashion: the two ships are perfectly lined up broadside to broadside, as in the images above and in the one below. However, in reality this was not the most common method. Ideally, the boarding vessel put its forecastle at the waist (basically, the center) of the ship to be boarded. This was to facilitate boarding by sending boarders aboard at the lowest part of the attacked ship. Plus, the main shrouds were located here, and this was by far the safest place to board an enemy ship.

And no, there was no swinging from one ship to another!

The usual variety of ship boarding arrangements is depicted below, with forecastle to amidships (no. 1) the most common.

Illustration from The Sea Rover’s Practice by Benerson Little (Potomac Books, 2005).

The second point to make is that boarding was generally undertaken only after the enemy’s fire was suppressed and, if possible, its decks cleared. Often, an attacked vessel’s crew would retreat to closed quarters (behind fortified bulkheads and below locked hatches) and fight from a fortified position rather than on the open decks. The point is this: boarders standing on the gunwales as the ships come alongside, as Hollywood has it, would be cut down by a hail of musketry, swivel gun fire, and great guns (as cannons are known as sea) loaded with small shot!

Two pirate ships engaged at “pistol shot,” soon to be “yardarm to yardarm” as they come alongside to board. Again, this is an easy way to shoot scenes like this, making it clear to the audience what’s going on. No, you wouldn’t see the fireballs and fiery explosions of which the film’s director was so fond! Publicity still from Cutthroat Island (MGM/UA, 1995). Author’s collection.

So, what might these boarding actions actually have looked like? Well, a minority may have looked somewhat like those above, albeit without men exposed on the rails until boarders were actually “away.”

“Slag bij Livorno” (“Battle of Livorno”) by Reinier Nooms, 1653 – 1664. Rijksmuseum.

In the painting above, three ships are yardarm-to-yardarm, with boarders attacking. All three ships are evenly alongside, as in the Hollywood images above. It is impossible to tell from the painting (accounts of the battle might provide the answer) which two ships came alongside first. A second Dutch man-of-war has come alongside in support of the first. Ideally, such support was provided by boarding across the deck of the allied vessel, but this, as the painting illustrates, was not always possible. To the right is another pair of ships equally alongside. In all these cases, boarding appears to have been intended: the sprit and sprit-topsail yards have been brought alongside the bowsprit and sprit-topmast respectively in preparation for boarding.

“Na de Zeeslag” (“After the Battle”), Reinier Nooms, 1652 – 1654. Rijksmuseum.

In the illustration above, the boarding action is more typical, if atypically backwards: facing opposite directions, that is. But the ships have their heads ideally placed amidships. This and the painting above are two of the few mid- to late seventeenth images actually showing boarders in action.

Detail from “Zeeslag met overname van een schip,” 1652 (?), Reinier Nooms, 1652 – 1654. Rijksmuseum.

Above is the classical, preferred method of boarding: ship’s had to the waist. The off-side ship has boarded the near, and boarders on the gangway from the quarterdeck to the forecastle (a common feature of many Dutch ships of this era) are attacking defenders in the waist below.

So, as with everything Hollywood, there’s usually a bit of truth at its core, but distorted for reasons of practicality of illustration, or ignorance, or sometimes even mere laziness. Even so, if nothing else, the Hollywood images do evoke the reality, at least from a distance!

And now, for fun: boarding in the manner of The Sea Hawk photo above would work only with Toons as shown below… 🙂

Cover image from the 1992 Looney Tunes Pirate Puzzle.

*The title quote is from Captain Blood starring Errol Flynn, screenplay by Casey Robinson (Warner Bros., 1935).

Copyright Benerson Little 2021. First posted January 25, 2021. Last updated August 15, 2021.