Should Miss America\'s Boss Step Aside

Lauren Daley

Ahoy, matey! Arrrrgh! Shiver me timbers and walk the plank!

… If you’re picturing a peg-legged, eye-patched flamboyant sailor with gold earrings, a head wrap, and a parrot on his shoulder, well, there’s a reason for that.

Centuries after their heyday, pirates are ubiquitous in pop culture, from Disney's "Pirates of the Caribbean" to Douglas Fairbanks as "The Black Pirate" in the 1920s to Robert Louis Stevenson's hit tale “Treasure Island” in the 1880s.

Just a few days ago, Sept. 19 was “Talk Like A Pirate Day” (apparently that’s a thing now.) As I’m writing this, #TalkLikeAPirate is trending on Twitter. And I guarantee you will see at least one pirate on Oct. 31.

So ubiquitous are pirates into our culture, that it’s easy for us to see them as cartoonish figures with swagger a la Jack Sparrow — but of course, they were actual people, some plundered our own New England waters, and in some ways, helped our early colonies thrive.

So we learn in historian Eric Jay Dolin’s “Black Flags, Blue Waters: the Epic History of America’s Most Notorious Pirates.”

This one just hit shelves a few days ago and it’s utterly fascinating.

Step aside, Johnny Depp.

We’re about to learn the true story of pirates, and they don’t walk and talk like Keith Richards. Dolin introduces us to a “rogue’s gallery of maritime plunderers.”

I picked it up to read the first few pages, and hours later, I was halfway through, glued to stories that felt lifted from movies, a colonial history I never learned in school, and a few pirates so brutal they could be characters in “Game of Thrones.”

Their adventures, the way pirates affected the early colonies, the pirates who roamed our own SouthCoast waters — it’s all just unreal.

Take, for example, Captain Edward Low, who a “particularly nasty pirate captain who prowled the waters by Cape Cod,” as Dolin told me.

In 1722, Low and his men plundered three ships right near New Bedford, off Block Island.

“The pirates viciously stabbed Captain James Cahoon of Newport,” Dolin told me, and then went to on “plunder a couple of fishing vessels off Martha’s Vineyard.”

Low forced half a dozen or so sailors to join his crew — then decapitated two of them.

“According to a diary entry of the Vineyard’s Rev. William Homes, a sea captain ‘sailing from the Eastward, found the dead body of a man floating upon the water with his head cut off…’” Dolin told me.

See what I mean by “Game of Thrones” characters?

You can see why pirates became the stuff of movies — every story told here feels ready-made for a screenplay adaptation.

And while the book is packed with tales like this, it’s moreover a meticulously researched history, an utterly engrossing story of the Age of Exploration, the early American colonies and how these lawless rogues fit into economics and history.

Mind blowing stuff.

Don’t miss Dolin when he speaks at the Westport Historical Society’s Annual Meeting, Oct. 18 at 6:30 p.m. The event is free and open to the public, at the Deedee Shattuck Gallery,,1 Partner's Lane, Westport.

You can also see him Sept. 28 at 6:30 p.m. in Falmouth at the First Congregational Church, 68 Main St.; and at the Hyannis Public Library on Oct. 6 at 2 p.m.

In our recent interview, I asked the Marblehead author: Who would’ve plundered SouthCoast?

“The most famous is certainly Samuel Bellamy, who [captured] a 300-ton British slave ship with 18 guns. The Whydah was chock-full of treasure [when] in April 1717, it encountered a terrific storm, and crashed off the coast of Wellfleet, sending Bellamy and as many as 161 other pirates to their death — and a vast amount of treasure to the bottom.

“In 1984, salvager and diver Barry Clifford and his team found the Whydah… They’ve recovered gold and silver coins, gold dust, guns, remnants of clothes, and wooden pieces of the ship… How much the recovered treasure is worth is not exactly clear. Estimates range from an unreasonably low $200,000 to a wildly improbable $400 million.”

Real-life sunken treasure (!)

Then there was “Thomas Pound, who terrorized the waters around the Cape and Martha’s Vineyard in 1689. They were finally caught by a ship full of armed men, who were ordered by Massachusetts Governor Simon Bradstreet to hunt them down… Pound and 13 of his men were found guilty of piracy, and sentenced to hang. In the end, however, only one of them was hanged in Boston — the rest were let off.”

The one local pirate I knew of before this book was Thomas Tew because of the Newport, R.I.-based rum.

Dolin told me: “In 1691, Tew convinced the crew on board his privateering vessel to go rogue, become pirates, and head for the Red Sea."

Tew "retired briefly from piracy, settling down in Newport” Doling told me.

(P.S. I love the idea of a retired pirate, "settling down." It’s like an SNL sketch.)

But arrrgh, the sea, she called to him.

“Many of his men had squandered their shares on drink and women, and they soon came round begging their former captain to embark on another trip — [but] Tew should have stopped while he was ahead... When he attacked a Mughal ship near the mouth of the Red Sea in 1695… a cannonball ripped into Tew’s midsection, disemboweling him.”

… Yikes.

As for the cruelest pirate? That goes to the aptly-named aforementioned Low.

"Once, when Low overtook a Portuguese ship heading to Brazil, he tortured its crew to find where they had hidden their valuables,” Dolin said.

One scared sailor “blurted out that the captain had dropped [their gold] into the sea, rather than have it fall into the hands of the pirates. Furious, Low cut off the captain’s lips and roasted them in front of his face, and then murdered the captain and the entire crew.”

… Ummmm.

Wow. Ok, we have a Cruelest Pirate winner.

They're despicable dudes, clearly, but I asked Dolin which pirate's story interests him most.

“Blackbeard, not only because of the larger-than-life mythology that’s grown up around his exploits, but also because he had one of the most interesting piratical careers, and his life ended in a bloody battle with his head being hung from the bowsprit of his own sloop,” he told me.

(These pirates and their decapitation, amiright?)

“Stede Bonnet, the ‘Gentleman Pirate,’ also fascinated me,” Dolin said.

“He was a wealthy plantation owner from Barbados, who decided to give up his comfortable life and become a pirate. He built his own pirate ship, and had the captain’s cabin lined with shelves so that he could bring along books… It’s not clear why Bonnet took the dramatic action of becoming a pirate. Some have speculated…. depression, or even insanity, while others have traced its origins to some “discomforts” he found in his married life. His life ended, like so many pirates, hanging from a rope.”

So why are we, as a culture, so fascinated by the scoundrels, plunderers and murderers? Why are they part of our pop culture canon, from books to film to our Halloween costumes?

“Even in the early 1700s… people were intrigued by pirates; their exploits were widely discussed,” Dolin said.

This cultural "fascination with pirates began well before Robert Louis Stevenson published 'Treasure Island' in 1883… A massive tome, ’A General History of the Robberies and Murders of the Most Notorious Pyrates,’ by Captain Charles Johnson (1724) really launched what we would term pirate-mania," he said.

"While much of his book was factually based, there were also plenty of fabrications and exaggerations, which helped fuel people’s interest in pirates,” Dolin told me.

“But, whatever the reasons, people seem to not be able to get their fill of the bad boys and girls of history — and that includes pirates.”

Buy the book, and learn more about upcoming events at


Lauren Daley is a freelance writer and book columnist. Contact her at She tweets @laurendaley1. Read more at


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