Some Terrible Cartoons About Terrible Pirates

The Gist: The scourge of piracy was ultimately defeated by punishment swift, certain, and severe.

The first of a three part  review of The Invisible Hook by Peter Leeson and

Under the Black Flag by David Cordingly.

For part one about piracy’s awesome benefits, check out Why You’d Want To Be A Pirate. For part two’s ode to pirate law, check out Republic of Pirates.

Ahoy me hearties! This email concludes the pirate trilogy. So far we’ve grasped that pirates were preferred employers and constitutional republicans. So why did everyone want to kill them? Did they just hate freedom?


Figure 1. “Everyone in my kingdom is free to follow my orders.”


They did hate freedom, but that wasn’t the principal reason. Pirates were not especially nice people. Pirates were thieves who committed larceny at the grandest scale. To achieve that end, they assaulted, tortured, and murdered victims who had the gall to resist.


Figure 2. Sadly, pirates did not actually make people walk the plank. Instead they did things much worse. If you are squeamish, skip the next two paragraphs. 


A gruesome standard was keelhauling, which involved tying you to a rope that circled under the ship and dragging you underneath to the other side, catching cuts from barnacles along the way. Or “woolding,” which described a favorite pirate technique that tied a rope around your head tighter and tighter until you talked or your eyes popped out. Montbars the Exterminator was a vicious original who preferred to “cut open the stomach of his victim, extract one end of his guts, nail it to a post and then force the wretched man to dance to his death by beating his backside with a burning log.”

Under the Black Flag describes the array of options (which were also available to tyrannical merchantmen): “It is usual nowadays to regard a sailing ship as a thing of beauty, but it could be turned into a torture chamber by a sadistic captain. There were boat hooks and brooms and iron bars to beat men with. There were axes and hammers and cutlasses to cause grievous wounds. There were ropes of all sizes which could be used to whip, strangle, and stretch bodies and limbs. The shrouds and rigging were ideal places for hanging up a stubborn man by his arms for a few hours. And after a man had been flogged till his skin was flayed off, there were barrels of brine to throw over the wounds and plenty of salt to add to the brine to increase the pain.”

So you can imagine the fear you’d feel standing in the crow’s nest at the top of your ship and spotting a Skull and Crossbones. That was precisely the point. The infamous flag was actually an invitation to surrender. The vast majority of pirate encounters left no one harmed precisely because they cultivated a reputation for inflicting horrors only upon resisters. Generally sadistic pirates had short and unprofitable careers. The successful pirate preferred not to fight because fighting meant his crew might suffer casualties, his ship might suffer damage, his treasure might not be captured. One Blackbeard biographer believes the man was an amazing marketer who never personally killed a man!

Before after

Figure 3. Going to that marketing seminar changed the course of Ed Teach’s career!


But even in the “best” of circumstances, pirates still were stealing literally tons of goods that did not belong to them. Black Bart Roberts, perhaps the most successful pirate, captured over 400 ships in three years – while maintaining the Sabbath!

weekly calendar

Figure 4. Bart was the cafeteria Christian of his day. 


So how was piracy finally scuttled? Britain gets the credit, but it took a really long time.

Fighting piracy was a logistical nightmare. The Caribbean alone is over a million square miles – and piracy occurred up and down the East Coast of the United States as well as all around Africa (Madagascar was an infamous pirate hideout). To catch a pirate, the Navy had to rely on gossip, intuition, and pirates continuing to ply their trade along sea routes. But the Navy didn’t choose to make it easy. As late as the 1700s, there were only four ships patrolling the East Coast and only three patrolling the Caribbean, all with mixed capabilities. To save costs, ships were for a long time undermanned and not allowed to resupply in the West Indies. They were also not allowed to careen, a process that grounded a ship for repairs and removal of barnacles below the waterline – something vital for speed. There was also apparently a practice of Navy captains using their ships for personal trading ventures rather than hunting pirates. Worst of all, for centuries, all pirates had to be taken back to England for trial.

Pirate globe

Figure 5. “Well, we have 10 ships. Where do you figure the pirates will be?”


Until 1536, a conviction for piracy in English courts required either a full confession or two eyewitnesses, neither of whom could be an accomplice. That was an incredibly high bar, especially as the witnesses were most likely sailors spread across the globe. Bizarrely, England allowed indicted pirates to plead not guilty but if they refused to plead at all, they would be tied to the floor and have heavier and heavier rocks placed on their chest until they pled or were crushed to death. Interestingly, to demonstrate that the Admiralty had jurisdiction, convicted pirates were hanged just off the shore, close enough for crowds to witness justice, but far enough out that their bodies would be submerged by the sea at high tide. 1536 provided only a marginal improvement by allowing accomplices to testify against each other. 

The most effective punishment is swift, certain, and severe. England only initially succeeded with the last. No wonder pirates operated with impunity (and were all the more preferred as employers!). Pirates were so little worried about being captured that they could take two days after confronting a ship to survey its cargo. If the Navy was truly on their trail, they had tens of thousands of places to hide until the Navy was forced to return to England. The most fearsome pirates had faster ships with more men and more guns than the standard Navy patrol. And even if against all odds they were captured, they still had to be transported thousands of miles to England during a journey where a lot could happen. And then multiple witnesses would have to be produced who had been at the scenes of the crimes those thousands of miles away. And after all that, a pirate on trial might present evidence in the form of a classified newspaper ad that he or someone else paid for advertising that he had been conscripted by a pirate crew. The pirate might beg for mercy and insist that he participated in piracy only to save his own life.

In the 1700s, Great Britain finally got serious. Pirates were an occasionally useful tool in harassing the Spanish and other European rivals, but they went too far when they threatened the British commercial empire. The British experimented with offering amnesty in hopes that pirates would give up their careers but it only had a limited effect: Woodes Rogers estimated that of 600 pardons he issued, 100 of the recipients were back pirating within 3 months.


Figure 6. “Are you still offering amnesty? I accidentally stole another few ships since my last one.” 


What really won the fight was financing the fleet and changing the law. Starting in 1700, merchantmen sailors who successfully defended their ships and cargo received financial bonuses. This principle was expanded in 1721 when the law provided that merchantmen sailors who failed to defend their ships and cargo forfeited their wages and suffered 6 months imprisonment. Captains of naval vessels who pursued personal profit over duty were finally punished. Anyone who traded with pirates would be treated as an accomplice. And most importantly, pirates could be tried and executed at sea or in the colonies. Suddenly, a pirate might be executed within days of capture. American Puritans had no tolerance for the traditional defense. The great preacher Cotton Mather ministered to captured pirates and violently reacted to their claims of conscription: “Forced! No; there is no man who can say he is forced unto any sin against the glorious God. Forced! No; You had better have suffered any thing than to have sinned as you have done. Better have died a martyr by the cruel hands of your brethren than have become one of their brethren.”

The Golden Age of piracy produced an attractive republican society. They were only able to do so because they operated outside the law, but it’s fascinating that they chose the structure they did. Unfortunately, it was built on a campaign of larceny and murder that governments allowed for too long. Ultimately, only the swift, certain, and severe delivery of justice brought their mayhem to an end. Thankfully a great republic arrived within a century to deliver on the promise of meritocracy and democracy.

Under the black flag

Figure 7. Under the Black Flag. Score 7/10. Some great stories about pirates, but a bit scattered.

Invisible hook

Figure 8. The Invisible Hook: 7/10. Fun premise worth reading, some arguments more interesting than others.

Thanks for reading!  If you enjoyed this review, please sign up for my email in the box below and forward it to a friend: Think – do you know anyone who loves history or the law? How about someone worried about crime? Or is there perhaps a person somewhere out there that isn’t yet fascinated by pirates?

I read over 100 non-fiction books a year (history, business, self-management) and share a review (and terrible cartoons) every couple weeks with my friends. Really, it’s all about how to be a better American and how America can be better. Look forward to having you on board!

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