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Black Flags, Blue Waters: How Piracy Has Shaped American History

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Eric Jay Dolin, Black Flags, Blue Waters, Notorious Pirates, Blackbeard
Illustration by Yuta Onoda - smithsonian.com

With Eric Jay Dolin, BestSelling Author of Black Flags, Blue Waters: The Epic History of America’s Most Notorious Pirates

As we impose tariffs against trading partners who aren’t playing fair, Steve’s guest reminds us that America’s role in the global ebb and flow of goods is hardly that of an innocent.  In his new book, Black Flags, Blue Waters: The Epic History of America’s Most Notorious Pirates, best-selling author Eric Jay Dolin recounts the scoundrels who terrorized the shipping routes of the Atlantic and Indian Oceans, unnerved the superpowers of the day, and ultimately reflected the brashness of the new nation to come.

State Sponsored Piracy

Starting in the late 1400s, Spain found great wealth in the mines of Central and South America.  Jealous of Spain’s success, Queen Elizabeth I, ordered one of her sea dogs, Sir Francis Drake, to attack Spanish galleons and bring back their treasures.  Drake did an excellent job and was knighted for his heroics.

The English viewed Drake as a successful privateer, but the Spanish viewed his attacks as pure piracy.

A century later, the British Colonial governor of Jamaica hired another famous sea captain, Henry Morgan, (aka Captain Morgan) and turned him loose on Spanish possessions.  They did this under Letters of Marque, licenses given to armed merchant ships with permission to attack and plunder enemy ships during times of war.

America In The 1600s

Fast forward to colonial America in the 1600s.  The Americans weren’t getting much support from England and had no representation in Parliament.  Great Britain looked at its colonies to enrich itself.  And navigation laws required that all goods to America pay customs duties to the Crown.

In frustration, American colonists turned to piracy.  In Black Flags, Blue Waters, Eric Dolin writes that Americans had no compunctions in welcoming these pirates home.  Boston and Newport even had the best money launderers, prostitutes, and grog houses to attract those pirates to their shores.

As a matter of fact, John Winthrop described a 1646 visit by pirates to Plymouth as divine providence, something they still celebrate every year in Plymouth.

As Eric Dolin says, greed and money often persuade people to view similar situations quite differently, depending on whether or not they’re benefiting from the money or being attacked and plundered.

Stve notes things aren’t all that different today, with people and governments openly or secretly worshiping at the altar of money.

The Pirate’s Code

In Black Flags, Blue Waters, Eric Dolin writes about life on pirate ships.  These ships drew up articles of the ship or the pirate’s code as it was called.

These codes specified how the money was to be split, how pirates could vote-in or vote-out as captain, where they would go in search of prizes, and which ships they’d attack.  Pirate ships were small, quasi-democratic floating societies, with rules that made then a cohesive fighting force.

Myths About Pirates…No Buried Treasures!

Eric also debunks the many myths about pirates, propagated in stories such as Treasure Island.  Pirates quickly spent what they looted.  There wasn’t really a culture of saving, adds a laughing Steve.

Eric attributes our fascination with dashing pirates to the vicarious allure of things we would never consider doing.  He dispels our romantic notion of being in control of our own destiny, going out on the open ocean, drinking rum, plundering at will, and living a long and fabulously wealthy life.

In reality, pirates didn’t make a lot of money, lived short lives, and were often hanged or forced to walk the plank.  There were no black eye patches or wooden peg legs!

To learn more about America’s history with piracy, check out Eric Jay Dolin’s Black Flags, Blue Waters: The Epic History of America’s Most Notorious Pirates.  The bottom line, says Steve, is to remember that lofty ideals were vital, but behind the scenes, money and greed played a major role in shaping the success of America.


Disclosure: The opinions expressed are those of the interviewee and not necessarily United Capital.  Interviewee is not a representative of United Capital. Investing involves risk and investors should carefully consider their own investment objectives and never rely on any single chart, graph or marketing piece to make decisions.  Content provided is intended for informational purposes only, is not a recommendation to buy or sell any securities, and should not be considered tax, legal, investment advice. Please contact your tax, legal, financial professional with questions about your specific needs and circumstances.  The information contained herein was obtained from sources believed to be reliable, however their accuracy and completeness cannot be guaranteed. All data are driven from publicly available information and has not been independently verified by United Capital.

Read The Entire Transcript Here

Steve Pomeranz: As we impose tariffs against trading partners who aren’t playing fair, my next guest reminds us that America’s role in the global ebb and flow of goods, is hardly innocent. In his new book, Black Flags, Blue Waters: The Epic History of America’s Most Notorious Pirates, he recounts the scoundrels who terrorized the shipping routes in the Atlantic and Indian Oceans, unnerved the superpowers of the day, and ultimately, reflected the brash of the new nation to come.

Eric J Dolan is the author and my guest. Welcome to the show, Eric.

Eric Jay Dolin: Thanks for having me.

Steve Pomeranz: Before we talk about the pirates and the business that they did with the colonialists, let’s talk about piracy itself before that. In the 1500s, Spain and England were mortal enemies, and there was some state-sponsored piracy as well, tell us about that.

Eric Jay Dolin: Absolutely, in the 1500s, starting in the late 1400s, Spain sort of took over a lot of the Western hemisphere. And they felt that it was their domain. They also found great wealth there in the mines, mints of Central and South America and lot of European powers including England were quite jealous of all this Spanish success.

So Queen Elizabeth I, the Virgin Queen, ordered one of her men, one of her sea dogs, Sir Francis Drake, to go to the Pacific Ocean and attack Spanish galleons and, hopefully, relieve them of their treasure, so that some of the wealth that Spain had commandeered through its conquest of the West could come back into English coffers.

And Sir Francis Drake did an excellent job. He overpowered and plundered a number of ships, came back to England, where he was knighted for his heroics. He wasn’t treated as a pirate by the English, of course, they viewed him more as a privateer. But the Spanish, of course, viewed Sir Francis Drake’s attacks as pure piracy.

And in fact, at the time, England and Spain were nominally at peace. So Sir Francis Drake was more of a pirate, and he was a privateer. But Queen Elizabeth was quite happy because the amount of money and treasure that he brought back was almost equivalent of a year’s worth of the income from the royal income.

So it was really a great win for her, and Sir Francis Drake was treated as a knight, and it’s basically true throughout history that nobody is called a pirate, unless their fellow peers call them so-

Steve Pomeranz: Yeah.

Eric Jay Dolin: So a lot of it is in the eye of the beholder.

Steve Pomeranz: Sure.

Eric Jay Dolin: Depends on whose ox is being gored.

Steve Pomeranz: Yeah, [LAUGH] one man’s ceiling is another man’s floor, that’s just the way it works. Now a century later the British Colonial governor of Jamaica hired another famous sea captain, Henry Morgan, and turned it loose on Spanish possessions, so I know that he was also very, very successful.

And they did this, these states did this under the guise of letters of marque—if I’m saying that correctly. What is that? What were those?

Eric Jay Dolin: Well, letters of marque are, basically, privateering licenses that during times of war, a government is legally allowed to issue a letter of marque to a merchant ship, an armed merchant ship.

That gives them permission to go out and attack the enemies of the country during the time of war and bring back the ships that they capture and have them adjudicated at admiralty courts and actually get part of the profits from those ships and perhaps get the ship itself.

So Henry Morgan was a buccaneer; he was a pirate for some time but also, he did get privateering licenses and some of them were issued during times when Spain and England were at war. Others were issued at times when that delineation was less clear and his acts were more piratical then privateering in nature.

But it’s important to point out that line between privateering and piracy is often quite thin. And many privateers veered into piracy, especially since both groups have the same set of skills.

Steve Pomeranz: [LAUGH] Let’s fast forward to colonial life in America in the 1600s. First of all, what was life like, let’s say for colonialists in the northeast and Boston and like? What were the actual living conditions and the difficulties they were facing under British rule then?

Eric Jay Dolin: Well, it was very difficult; they were on the edge of empire. Here they were, hugging the coast of the American colonies, not getting a lot in the way of support from the mother country, certainly not having any representation in Parliament or the affairs of the mother country.

And England really looked at their colonies, not only their American colonies, but their other colonies as ways to enrich the central powers. So the Americans were feeling a little bit left out and condescended to, and they also had a difficult time getting currency with silver and gold, and they were often forced, and they were, in fact, forced by the British government to pay for their a lot of their goods with currency, yet the colonies were often starved of the very thing that they needed to enrich their own lives.

And also the navigation laws required that all goods coming into the colonies had to first be trans-shipped through England and that entailed additional customs duties and made many of the products more expensive. So it’s no surprise that many American colonists, even in the late 1600s, well before the American Revolution, were feeling somewhat abused by the mother country.

And they had good reason for feeling that way.

Steve Pomeranz: Yeah, and so they were in kind of desperate straights, so here come the pirates now who are kind of a knocking off all of these merchant ships and other things like that. And then bringing that money and that booty to the shores of this young, early pre-country, and they were getting the money they needed, they were getting the goods they needed.

And I understand from your writing that Boston and Newport had the banks with the best-skilled money launderers and also some of the best prostitutes and grog houses in the world. So there were more attractions to bring in those pirates.

Eric Jay Dolin: Yes, yes, a lot. The colonies did compete to give higher rates or fees for sort of laundering foreign money or Spanish silver dollars.

And so the pirates could get more bang for the buck if they went to certain colonies. But one thing that’s really important to mention in connection with the piracy that took place in the late 1600s, much of it was American ships with Americans on board. People from the colonies going around the Cape of Good Hope into the Indian Ocean and attacking Mughal or Muslim ships coming from India, that were transiting to the Red Sea and the port of Jeddah and Mocha.

And they had plenty of treasure on board and one of the things that made it easier for Americans at the time to accept this form of piracy—even though those Red Seamen were given privateering licenses because it was during King Williams war and France and England were at war—those privateering licenses were basically just covers.

They were not privateers, they were pirates going in the Indian Ocean, but what they were doing, is they were plundering these, quote-unquote, infidels or heathens halfway around the world and bringing that money back to the colonies. So the colonists who often labeled these Red Seaman as privateers, even though they weren’t, didn’t have any compunction against supporting them because they were attacking people they looked down on anyway.

And then they were bringing all this great stuff back to the colony.

Steve Pomeranz: Yeah, I mean, they were the heathens. They didn’t care about the heathen; they were less than human, so they didn’t really care. That kind of, in a way, kind of juxtaposes the fact that New England and Boston was really kind of ruled by a Puritan autocratic kind of government in morality, and yet, in this case, I guess they looked the other way.

As a matter of fact, John Winthrop described a 1646 visit by pirates to Plymouth as divine providence, and actually, I went online and I find they’re still celebrating that today, in Plymouth every year they have a celebration, yeah.

Eric Jay Dolin: It seems throughout history, one of the things that’s really fascinating about pirates and to be reflected in so many elements of American or world history is that money talks.

And money often persuades people to view similar situations quite differently, depending on whether or not they’re benefiting from the money, or they’re the ones being attacked and being plundered. So the colonists really had no problem with this money. And even though perhaps it didn’t square with their religious morals to some extent, they were willing to accept it.

Later on, in the 1700s, when it was the colonists and their interests that were being attacked by pirates, they were singing quite a different tune. But again, greed and money determined the course of American history and world history very strongly.

Steve Pomeranz: Yeah, and I don’t think things are much different today.

As a matter of fact, we see very much the same parallels between kind of the have and the have-nots as well. My guest is Eric Jay Dolin, the book is Black Flags, Blue Waters: The Epic History of America’s Most Notorious Pirates. We don’t have that much, but I was interested in the surprising way in which pirate ships were governed.

How did they manage their own affairs?

Eric Jay Dolin Well, they were largely democratic in nature, but don’t confuse them with sort of being political philosophers. Basically, what they did is they drew up the articles of the ship or the pirate’s code, as it was called, and in that, it would determine how the money was split.

And often the money on a pirate ship is split almost equally with the captain and the quartermaster and perhaps a medical person if he was onboard receiving a little bit more. The pirates also had the opportunity to vote for who would be their captain, where they would go in search of prizes, and which ships they would attack.

And along with this voting ability for their captain, they also could depose the captain who they felt was not doing a good job, and that happened quite a bit. So, yes, they were democratic in nature, but it was really because they were a floating society and they needed to establish rules that would make them become a cohesive fighting and threatening force.

And you have to keep in mind, many pirates mutinied on merchant ships, killed their despotic captains, took over the ship, and launched into piracy. So it makes sense that those very people who had been lorded over by one individual would not want to recreate a system on their pirate ship where there was too much power concentrated in the hands of one man. So that was in large part the reason, why they voted their captains in, and then voted their captains out. So it is a fascinating floating society, but again, don’t draw any parallels between the democratic principles that the pirates had in the early 1700s, and the democratic principles on which the American Revolution turned.

Steve Pomeranz: Well, these people were ruthless, they were scoundrels, they didn’t mind killing and stealing and doing what they needed to get what they wanted, so-

Eric Jay Dolan: Yeah.

Steve Pomeranz: Now I don’t think I will confuse them again. How about using Democratic principles and opining on that?

We have a lot of myths about pirates. For example, Robert Louis Stevenson in Treasure Island wrote of buried treasure. Was there ever any buried treasure?

Eric Jay Dolan: There’s no record of any pirate during the Golden Age burying their treasure. They often spent it as fast as they got it and just think about it.

If you bury a treasure, that implies that you’re going to be able to get back there sometime in the future and that was not necessarily guaranteed. Also if you buried your treasure, somebody else might find it and they like to keep the treasure nearby and when they had opportunities in ports of call to spend it, they did.

Steve Pomeranz: Yeah, so, there wasn’t really a culture of saving. [LAUGH]

Eric Jay Dolan: No, there weren’t good money managers.

Steve Pomeranz: No 401Ks there.

Eric Jay Dolan: [LAUGH] The few pirates that got a lot of money, and I have to emphasize that it was a few, it’s amazing how many pirates really failed to achieve much in the way of wealth.

But the few that did manage to get their hands on a lot of money often didn’t do very well with it over time if they even survived.

Steve Pomeranz: Not surprising. So why are we so enticed by these kinds of images whether it’s the Western gunslinger, or the prohibition era bootlegger, and the pirate, we’ve got these dashing leading men, Errol Flynn, so many years ago, and Johnny Depp today—I don’t know how dashing he is, but he’s different. The bottom line is why are we so attracted to these people, is it because they go against society?

Eric Jay Dolan: I think that’s certainly part of it, the allure of reading about people that do things that you in your own life would never even consider doing.

And sort of the abstract notion of being in control of your own destiny, for a pirate, going out on the ocean, being on a ship with other men, drinking rum, plundering at will, and hopefully, living a long and fabulously wealthy life. Now, unfortunately, the reality of it was nothing like that.

Steve Pomeranz: Well, most pirates didn’t really make any money.

Eric Jay Dolan: Right, most pirates not only didn’t make any money, they lived relatively short lives, and many of them found the end of their life at the end of a rope, being hanged.

Steve Pomeranz: Yeah.

Eric Jay Dolan: So, another part of it is what you mentioned.

Hollywood, Errol Flynn, I mean, the leading men, the rakish rapscallions, the good-natured thieves on the ocean. Those images that we’ve seen in so many movies starting in the early to mid-1900s have had an indelible impact on how we view pirates. And then there’s some other thing, you have to talk to a psychologist to get the answer to this ‘cause I still am puzzling about it.

But why do people love reading about the bad boys and girls of history, people who do horrific things? Be it a murder mystery or a war or something else, things that are really wrenching, difficult to read about, and that you probably wouldn’t want to be involved in, nevertheless, create such a compelling narrative that people are drawn to it. And I think pirates benefit from that to some extent. And it’s exciting to dress up with a patch, an eye patch, a hook for a hand, which is another myth. Going around saying argh and matey.

Steve Pomeranz: What about wooden leg? Not many wooden legs, I understand.

Eric Jay Dolan: I came across no pirates with peg legs, however, there were men at the time, sailors who had their legs blown off by canons.

Steve Pomeranz: Yeah.

Eric Jay Dolan: They did get prosthetics that were, in effect, wooden legs as well as claw hands. But it’s difficult being on a ship when you have two good legs and two good hands.

Steve Pomeranz: Yeah.

Eric Jay Dolan: Imagine the difficulty getting around without that.

Steve Pomeranz: All right, well, the book is about pirates. It’s a great little book, Black Flags, Blue Waters: The Epic History of America’s Most Notorious Pirates.

And I think the bottom line here is to remember that money and greed and that rather than the many lofty ideals that we would like to believe shaped the expansion and the success of America—rugged individualism, things like that—which, of course, did exist, but equally so or to a great degree so, money and greed also had a lot to do with that. My guest, Eric Jay Dolan.

And to hear this in any interview again or if you have a question about what we’ve just discussed visit our website at stevepomeranz.com to join the conversation. And while you’re there, sign up for our weekly update for a brief rundown of the important topics we’ve covered that week, straight into your inbox.

That’s StevePomeranz.com. Eric Jay Dolan, thank you so much.

Eric Jay Dolan: Thank you.