And indeed he was a picturesque — and picaresque! — fellow, the buccaneer! Howard Pyle’s painting of this romantic sea rover has influenced the imaginations of half a dozen generations of readers, writers, illustrators, costume designers, film-makers, and game designers. Currently on view at the Delaware Art Museum, the painting was one of four created for an article, “The Fate of a Treasure Town,” also by Pyle, published in Harper’s Monthly Magazine, December 1905.

In fact, the paintings accompanying the article are some of Pyle’s most famous buccaneer and pirate images. In addition to the picturesque buccaneer, there is “An Attack on a Galleon,” “Extorting Tribute from the Citizens” (used as the cover of The Buccaneer’s Realm, for what it’s worth), and “So the Treasure Was Divided.” Of the most famous paintings of his buccaneer, as opposed to pirate, series, only “Which Shall be Captain?” for “The Buccaneers” by Don C. Seitz, in Harper’s Monthly Magazine, January 1911, and “How the Buccaneers Kept Christmas,” Harper’s Weekly, December 16, 1899, are missing. (High resolution images are available on Wikimedia Commons.)

Pyle’s article opens with romantic tropical buccaneering scene-setting, then shifts in detail to the sack of Cartagena de Indias in 1697, a privately-funded French privateering expedition that was composed of hired ships and troops of the French navy and army, with a large body of French buccaneers and Caribbean militia in support. The Baron de Pointis, commander of the expedition, swindled the buccaneers out of their agreed share, so they returned and extored more treasure from the citizenry. Pyle’s painting, “Extorting Tribute from the Citizens,” shows buccaneers actively engaged in this pursuit. (On a side note, the painting was used for the dust jacket of The Buccaneer’s Realm, my second book.)

But few people have actually the read the article or even know about the sack of Cartagena de Indias, and it’s the images themselves that have caught our imagination. In particular, film-makers, illustrators, and Disney have borrowed heavily from the paintings: from The Black Pirate of Douglas Fairbanks and the Captain Blood of Michael Curtiz, to Disney’s Pirates of the Caribbean attraction and films, to the sea rover art of Don Maitz, Pyle’s influence is impossible to deny.

From a historical standpoint, the paintings are far more evocative than accurate, although clearly Pyle attempted to get historical details correct. But this wasn’t easy. He had to interpret written descriptions and also — the bane of truth-seeking historians and researchers everywhere! — appeal to popular tropes as well. For popular works, some degree to catering to popular expectations is considered mandatory, or so I’ve been advised (and immediately resisted, bound by nature to do my best to keep within the limits of fact and fact-finding, at least as much as possible).

For Pyle, it was not the buccaneer or pirate’s sea roving escapades that made him appealing: “It is not because of his life adventures and daring that I admire this one of my favorite heroes; nor is it because of blowing winds nor blue ocean nor palmy islands which he knew so well; nor is it because of gold he spent nor treasure he hid. He was a man who knew his own mind and what he wanted.”

He conveyed this well with his picaresque — sorry, picturesque — buccaneer even if it appears that the young man evokes a purely romantic image of a sea roving adventurer rather than a real one.

Let’s take a quick look at his arms, accoutrements, and clothing and compare them to the historical. We’ll begin with his hat. Spotting the red ball tassels, we assume the hat is intended to evoke Spain — it’s the somewhat tropish hat of a Spanish flamenco dancer or mounted matador. Perhaps the buccaneer captured it, or, I think more likely, the buccaneer is in fact a Spaniard, a mestizo perhaps. We know that there were Spanish renegados among the buccaneers. Let’s keep this in mind as we look at the rest of him.

He’s wearing two gold earrings — small simple hoops. Most European-derived buccaneers did not wear earrings, with the occasional exceptions of the Dutch (single pearl, single ear), fops (single pearl, single ear). However, all too often our impression of pirates is influenced by our ethnocentrism: some Africans, Native Americans, mulattos, and mestizos in the Americas did in fact wear earrings. Pyle probably added earrings as part of the expected pirate cliché, but to my mind, the earrings, considered historically, are more evidence that this buccaneer is a Spanish mestizo renegade, as is the perhaps fanciful bracelet on his wrist. His dark hair and olive skin — also “Spanish” clichés — are to me more evidence of his Hispano-American origin.

He has a red cloak over his shoulders, but would a buccaneer wear one? Probably not in the daytime, given the highs in the upper 80s and lows in the upper 70s year-round in Cartagena de Indias, although in some areas of the Caribbean cloaks, jackets, blankets, “ruggs,” &c were worn or used, typically at night. That said, a 1680s image, if not eyewitness then at least based on eyewitness descriptions does show a Spanish pirate or privateer with a cloak! More on this below.

Further, French priest and eyewitness Jean-Baptiste Labat described the admiral of the Armada de Barlovento in the Caribbean as wearing a cloak, but he was an old man and perhaps needed the cloak to keep his old bones warm at sea. And Spaniards wearing them are depicted in period images of New Spain, see the last image below for example. Perhaps, as with the Spaniard’s ruff which was often added historically as a satirical symbol — Spaniards no longer wore ruffs –, Pyle added the buccaneer’s cloak as a mere symbol of dress to indicate that the man is a Spaniard. This isn’t the first time Pyle put a cloak on a buccaneer: he also did so in his painting, “How the Buccaneers Kept Christmas,” Harper’s Weekly, December 16, 1899.

His “musket” is a bit of an anachronism: it is a Jaeger or Jaeger-type hunting rifle. Developed in the late 17th century in the region later to become known as Germany, there is no indication they were ever used by buccaneers. These Caribbean sea rovers used the long fusil boucanier, especially among the French, and various other muskets at times. However, there are instances of carbines (Sp. carabinas) in use on occasion at sea and ashore, and we will assume this is what Pyle meant to represent. His pistol could represent any number of sea pistols in use at the time, and is close to their common size. Its lock is indeterminate, but it hints of a Spanish Miquelet style.

His rapier, or possibly broadsword, is a shell-hilt, of what could be a Spanish-style doble concha, although the true cup-hilt (taza) was far more common. All or nearly all English, French, and Dutch buccaneers carried cutlasses, although there are documented indications of a few exceptions for smallswords and broadswords. However, the rapier — espada ropera — was still in common use in Spain, Portugal, and Spanish-governed parts of Italy at the time, not only among gentlemen (and most Spaniards considered themselves gentlemen!), but also among soldiers and almost surely among some seamen and artilleros. In fact, the eyewitness, or nearly so, image below of a Spanish privateer or pirate from the 1680s shows him wearing a Spanish rapier. Curved quillons were uncommon on Spanish swords of the era, although they did begin to show up on some at the end of the 17th century. Again, although for Pyle the rapier may have been a necessary trope, historically it would point the buccaneer being a Spaniard, Portuguese, Italian, or Corsican.

His sash is a bit wide, at least from what eyewitness images suggest, but his belt is correctly worn over it. The pouch or box on his right may be a cartouche box worn on a strap in a rather un-buccaneer style. His breeches, buttoned at the sides, are quite typical of those shown worn by Spaniards in the era, although Pyle may have depicted this style to evoke the swashbuckler or pirate as he did in other paintings, “I Had Met My Equal” for example.

And last, his sandals: most buccaneers, according to eyewitness descriptions and images, wore conventional shoes, or boucanier shoes made from skin pulled from the hocks of hogs (see here for details), or went barefoot, at least among the poorest sort. However, as noted not all buccaneers were English, French, or Dutch. Some were Spanish renegades, including Spanish Native Americans and mestizos, and we know that some of both groups wore sandals at the time.

The image below was drawn by a French engineer in the 1680s, almost certainly based on local eyewitness accounts of French pirates or privateers who attacked Nipe on Saint-Domingue (modern Haiti). There is no chance Pyle ever saw this image, yet his picturesque buccaneer evokes it well! The Spaniard is even wearing a cloak! Many Spanish pirates and privateers — most, some eyewitnesses noted — were men of color: Native Americans, mestizos, Africans, and mulattos. Is this what Pyle intended, a Spanish or mestizo renegade buccaneer? I can’t be entirely certain, but the evidence and my gut assure it is.

Bookends, Bookcovers, & More…

The painting has inspired a variety of objects and art, ranging from bookends to bookcovers to game miniatures. The bronze-clad bookend below, “Pirate’s Den” by Peter Manfredi (1930) for the Pompeian Bronze Co., is a three dimensional copy of Pyle’s painting. This example is one of two variants; the other has part of the background removed.

The Pompeian statuette bookend below, “Buccaneer” by Peter Manfredi (1930), was clearly inspired by Pyle’s painting. On the left is “Miss Pirate” by the same sculptor and year for Pompeian Bronze Co., Brooklyn.

In The Black Swan (20th Century-Fox, 1942), only loosely based on Rafael Sabatini’s novel of the same name, Tyrone Power’s costume is clearly based on, and probably an homage to, Pyle’s famous painting. The hat with tassels hanging from it, the cape, the sash, the rapier, are all clearly intended to evoke Pyle’s picturesque buccaneer.

The image has been used often on the covers of trade paper editions of Captain Blood: His Odyssey by Rafael Sabatini. The one below is published by the Naval Institute Press. Pyle’s painting doesn’t evoke the urbane and sedulous Captain Peter Blood, but it does evoke the buccaneers he led. In fact, part of the novel takes place during the sack of Cartagena de Indias, although Sabatini moves the attack on the beautiful city up in time.

The painting inspired the cover of a mass market edition of Cup of Gold by John Steinbeck, a fictional, and quite literary, account of famed buccaneer Henry Morgan.

CrossGen published a series of six comic books 2003-2004 by Chuck Dixon, Steve Epting, and Frank D’Armata featuring a Spanish female pirate hunting captain, Donessa Cinzia Elena Marie Esperanza Diego-Luis Hidalgo (seriously!). Captured by buccaneers in 1687, she turns them into pirate hunters to seek out and destroy their pirate lord in return for the location of a great treasure. Commanding El Cazador, she is known by her English and French crew as Lady Sin and Captain Sin. She appears on the cover of Issue 5 (March 2004) in an homage to Pyle’s Picturesque Buccaneer. My many thanks to Antón Viejo Alonso for reminding me of this comic book cover!

The Naxos re-release of these film music classics by the Brandenburg Philharmonic Orchestra uses the picturesque buccaneer on the “album” cover, albeit reversed. Good music too!

Firelock Games created a special edition figure as an homage to Howard Pyle for its popular (and quite historically accurate) Blood & Plunder tabletop wargame. (Full disclosure: I’ve done quite a bit of consulting for Firelock Games.)

Even produce growers, or at least one of them, have appropriated the swashbuckling image…

Perhaps the most significant homage to Pyle’s painting came from another great illustrator: Norman Rockwell. But Rockwell’s buccaneer is no longer the youthful adventurer with a touch of arrogance, but a tired grizzled veteran with torn cloak and shirt, a sash of a different color, a hat that has long lost its tassels, and a leg lost to a broadside, yet who keeps sailing the Main with his buccaneer brethren even as he begins to long for home. There are a few anachronisms, as there always are in such paintings: his pistol is of a later era, as is the cutlass that has replaced his rapier, and his boots are entirely fanciful and unhistorical — pirates didn’t wear any such footwear. But I find no real fault with such details. As I said, these are evocative, not historical images.

But I do find fault with the home Rockwell has the buccaneer dream of, for it evokes Olde England as N. C. Wyeth might have painted it — perhaps even the Admiral Benbow Inn! — and not Spanish America. I imagine our Spanish renegade buccaneer, young and old, longing instead for a place along the Spanish Main: Campeche or Veracruz, Havana or Matanzas, Puerto Bello or Maracaibo. Or perhaps he’s even from Spain! But no matter: he has chosen to sail with the hated buccaneers, and might never see his home or family again. But let us remember that these are only paintings, only part of the story: we might fill and finish the buccaneer’s tale as we please.

Copyright Benerson Little 2022. First posted August 17, 2022. Last modified March 6, 2023.