Fiction, Fact, and Fancy: Downstate Pirates and Swashbucklers


Once upon a time on a dark evening in 1748, a river pilot was heading up the Delaware Bay, having just escorted a ship on its way to Philadelphia safely past the tricky shoals of Cape Henlopen. Suddenly, a small boat appeared seemingly out of nowhere, pulled up beside the pilot’s boat and a number of Spaniards clambered aboard and proceeded to despoil him of a ring, shoe buckles, and over two pounds of money.

The Spanish pirates also took away his clothes, his food, and all the sails. They left him with only some moldy bread and some greasy water. Upon withdrawing, they opened fire on the pilot boat.

Needless to say, there was no gold, silver, gems, or exotic spices for these pirates to plunder, not like in the Caribbean. Just some shoe buckles and a ring. That’s what I call piracy, downstate style.

Pirates were first documented in Delaware in 1685. The many European wars during the 17th and 18th Centuries created opportunities for Spanish, English, Dutch, and French pirates to troll the Atlantic coastline and rob ships and towns. Lewes, due to its strategic location at the mouth of the Delaware Bay, was attacked several times by lesser-known pirates. In 1698, a ship commanded by a pirate named Canoot attacked the town. Fifty well-armed men plundered houses of money, sheep, and hogs. They even kidnapped the town carpenter.

Who’s ever heard of the pirate Canoot? And, more importantly, what did they do with the carpenter?

Delaware back then was part of William Penn’s Quaker colony. The pacifist Quakers wouldn’t confront the pirates. As a result, piracy in and around the Delaware Bay was a problem up until 1750 when the British Navy positioned several warships off the coast and cleared the Bay and capes of enemy ships.

You might think that’s the end of pirates and Delaware, but you’d be mistaken. Delaware, you see, has a stronger bond to pirates than most people know.

Many, if not all, the images we have of pirates today come from Hollywood and its movies featuring romantic, heroic, swashbucklers played by handsome men like Errol Flynn, Tyronne Power, and, more recently, by Johnny Depp. This romantization can be traced back to Gilbert and Sullivan’s 1879 opera Pirates of Penzance, Robert Louis Stevenson’s 1883 novel Treasure Island, and to Howard Pyle, a Delaware artist who was one of the most influential American illustrators of the late 19th Century.

Pyle’s stories and illustrations appeared in many of the country’s most popular magazines. He had a taste for romantic and chivalric history, fact and fiction — the American Revolution, Robin Hood, King Arthur.  

Pirates were among his favorite subjects, and he excited the reading public with stories and illustrations of Captain Morgan, Blackbeard, and Blueskin, attired in headscarves, earrings, and velvet sashes; dueling; burying treasure; drinking rum. It’s been said that Pyle was to pirates what Remington was to Indians and gun fighters of the American West.
Howard Pyle, though, was a serious artist. He founded art schools in Wilmington, Delaware, and then in nearby Chadds Ford, Pennsylvania, along the Brandywine River. His style and students became known as the “Brandywine School,” and it produced many renowned artists.

Pyle drew inspiration from the Delaware coast. I’ve read that he vacationed in Lewes and later owned a summer cottage in Rehoboth Beach, where some of his most successful students, including N.C. Wyeth and his young family, often spent time with him. It’s been said that many of Pyle’s pirate illustrations were painted during the summer or painted from sketches made along the Delaware seashore. Interestingly, N.C. Wyeth would go on to do the illustrations for a 1911 edition of the pirate novel Treasure Island.

Howard Pyle died suddenly of a kidney infection in 1911 at the age of 58 while in Florence, Italy, where he’d gone to study mural painting. Ten years later, his fictional pirate stories and illustrations were compiled into a volume called Howard Pyle’s Book of Pirates, from which comes the image accompanying this column.

What was it about pirates that so enthralled Pyle? A taste for rum? For a little sodomy, perhaps? I can certainly appreciate both.

Some clues can be gleaned from Pyle himself, where he writes, or I should say, asks his readers to ponder: Why is it that a little spice of deviltry lends not an unpleasantly titillating twang to the great mass of respectable flour that goes to make up the pudding of our modern civilization? And would not every boy, for instance rather be a pirate captain than a member of Parliament?

Hmm, I’m not so sure about that. Some of those Lords live pretty well. But, I do think Pyle recognized that deep down there’s a bit of pirate in all of us. That must explain all the swashbucklers today looking for rum and booty on Baltimore Avenue. Don’t you think?

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