So You Want to Become a Pirate…

It’s easy to understand. The life of piracy has not lost its appeal. Perhaps you have in mind becoming something dashing like Errol Flynn in his depiction of Captain Blood? Or perhaps the erratic and mischievous Jack Sparrow? — sorry, Captain Jack Sparrow! Maybe you’re more inspired by the famous, popular figure of Long John Silver? You probably don’t want to end up like Captain Hook, however. These figures — though, alas, purely fictional — were based on a reality that some might consider all the more intriguing for its truth. In this post we’ll have a look at some of the figures whose exploits defined the Golden Age of Piracy in the Caribbean. These men and women, though they often lived short and violent lives, nonetheless inspired whole sub-genres of historical fiction and fantasy across a variety of media, as well as exciting significant scholarly interest. Before we get into them, however, you must first ask yourself: Why do you want to become a pirate?

The Allures of Piracy 

One of the hallmarks of piracy, especially in the early-eighteenth century, is its particular brand of egalitarianism. Unlike on British naval vessels, where the bulk of the prize money for captured enemy ships went to the captain and the officers, the pirates shared their winnings much more evenly. The code-of-conduct attributed to Bartholomew Roberts in Captain Johnson’s A General History of Pirates — one of the key primary texts on piracy — states that a captain and quartermaster get two shares for every one share that the rest of the crew get, with other officers getting one-and-a-half. Some observations put the captain’s share at only 50% more — compared with 1400% more on a privateer. Decisions would be taken by a council called on board the ship, with every sailor getting a vote; the captain himself may be voted in — or voted out. Benjamin Hornigold, for example, was voted out as captain when he refused to plunder English ships.

More broadly, you might be attracted to the libertarianism or republicanism of pirate life. The Pirate Republic, established on Nassau after the end of Queen Anne’s War in 1713, has been seen as a precursor to the American Republic that was established from 1776. Piracy attracted a range of individuals, from sailors dissatisfied with life on board merchant or naval vessels, to people of African descent who had escaped slavery. All were, or saw themselves as, victims of monarchical tyranny, and sought to free themselves from the yoke of whichever crown they were subject to. Much of their newfound liberty had a particularly masculine edge — many women in pirate communities found themselves still confined to the role of boarding house keeper or prostitute. But that did not preclude women from being pirates, as we shall see.

And then there is perhaps the strongest appeal of all — treasure. Above all, you want to become rich. This has been the key motivating factor from the early days of piracy in the Caribbean. Sir Francis Drake, committing piracy in all but name under the sponsorship of the English crown, attacked mainland Spanish America and captured Spanish ships. The prize was Spanish gold, dug from the ground by enslaved indigenous and African labour, and destined to fill the coffers of Spain. Gold similarly motivated Sir Henry Morgan, who led a series of raids against Spanish settlements, most famously in Panama. And it motivated the series of pirates, like Sam Bellamy, who flooded to Nassau after rumours spread of a wrecked Spanish treasure ship along the Florida coast.

So, now that we’ve established why you want to become a pirate, let’s see what company you will be in.

Meet Your New Captain

During the Golden Age of Piracy, thousands of people flocked to the Caribbean and, whether intentionally or not, found themselves going ‘on the account’, as they used to say. It is not possible to discuss all of these figures in this short post, so we might focus our attention on several who stand out.

As previously mentioned, Francis Drake was one of the earliest of the Caribbean’s pirates. But was he really a pirate? The term might need some clarification — he might not have considered himself a pirate. Rather, he acted as a privateer, receiving the sponsorship of Queen Elizabeth, granted in the form of a letter of marque that entitled him to attack non-English shipping. He was joined by his contemporaries Sir Walter Raleigh, Sir Richard Grenville, and Sir John Hawkins. These men, pirates to various degrees, led English raids against Spanish coastal settlements in South America in the search for gold that might enrich Royal coffers, as well as themselves. They furthered English colonial expansion in the Americas and provided the basis for more permanent settlement.

The pirates of this earlier generation were followed by the likes of Henry Morgan — you may know Morgan well already from the bottles of rum which, like the pirates before you, have led you to many a bad decision. Sir Henry Morgan, hailing from Wales, became a true buccaneer. He began his career as a soldier, joining an expedition in 1654 to capture the island of Hispaniola, which now is split between the Dominican Republic and Haiti. After falling to capture this island, however, the invasion force moved to wrest Jamaica from Spanish hands. The island was to become the jewel of the British Empire. Morgan spent the rest of his career raiding Spanish settlements in South America, just as Drake had, later becoming arrested for his attack on Panama, forgiven, and then knighted in recognition of his achievements.

Among the ranks of pirates were not just those who took part in the imperial project, but freelancers, explorers and naturalists. One of the most famous of these is William Dampier, the first person to circumnavigate the world three times. It is true that Dampier joined a series of buccaneering adventures — he was with Captain Bartholomew Sharp at Panama from 1679, and he returned there again some years later under different command. But he also travelled extensively, documenting his observations. It is because of his travel writings, published later in his life, that we have such vivid descriptions of logwood cutters in the Bay of Campeachy, and how we have observations about early Australia and Indonesia. He became one of several at the time to gain celebrity status from his published exploits, joining Alexandre Exquemelin, whose own text documents in graphic detail the exploits of French and English buccaneers who lived on Tortuga. Dampier’s book was followed by one by Woodes Rogers, with whom Dampier had sailed later in his career, and of whom we will learn more shortly.

Though these works have formed the basis of much of our understanding of piracy and buccaneering in the 17th Century, many of the pirates who have captured our imagination hail from what was in reality a rather brief period of history some years later. From 1702 until 1713 England (Britain from 1707) was at war with France and Spain. As in previous wars, letters of marque were given to private crews to attack belligerent shipping. Many men built their careers here. Some were satisfied with their exploits during the war. For others, however, the return to peace in 1713 was too much to bear. Some continued their raids against Spanish and French shipping; some, such as Henry Jennings, with the backing of the Governor of Jamaica. Another, Benjamin Hornigold, was credited with establishing the free Pirate Republic at Nassau in New Providence. 

This generation of pirate gave breed to another — Jennings oversaw the rise of the vicious Charles Vane, who, at his peak, “presided over an orgy of violence and cruelty”, according to the historian Colin Woodard. The truth of this is debated — it may well have been an exaggeration by colonial officials, but either way it cemented his reputation. And reputations were important — Blackbeard, born Edward Teach (or Thatch), was tutored by Benjamin Hornigold, and cultivated for himself a fearsome reputation. He is noted for putting slow burning fuses in his beard that added to his fierce appearance. His reputation meant, however, that his prizes were more likely to surrender, and this helped him avoid violence and torturous behaviour.

All of the individuals mentioned thus far have been men. Could women not be pirates, also? The answer is yes — some of the most fascinating figures in the history of piracy have been women. Indeed, one of the fiercest pirates of all time was Zheng Yi Sao, a pirate queen who operated in China in the early-nineteenth century. In the Caribbean, most famous are perhaps Anne Bonny and Mary Read. The two sailed with Calico Jack Rackham, Charles Vane’s former quartermaster and a captain known for his flamboyant dress. Rackham’s fame, however, stemmed principally from his decision to sail with Bonny and Read. The two women dressed as men and fought valiantly alongside their male comrades. They were also captured and tried alongside these men. But their fate was not the same — though both were sentenced to hang, they escaped the noose by revealing that they were pregnant. Both were, it seems, though Mary Read did not benefit much by this, for she died in prison later. It is not clear what happened to Bonny.

There are, of course, numerous others who I have not mentioned. The legend of William Kidd and his buried treasure, or Stede Bonnet, the ‘Gentleman Pirate’. There are also pirates and buccaneers of other nations, such as the Frenchman François l’Olonnais. Another time, perhaps. For now — and purely for the sake of balance — you might want to consider some reasons not to become a pirate.

It’s a Hard-Knock Life

The main reason not to become a pirate is that it will severely shorten your lifespan. Few pirates were known to retire — one of the most famous exceptions was Henry Every, who gained a fortune from seizing the shipping of the Grand Mughal of India. He managed to evade capture with his wealth, though it is questionable whether he managed to hang onto it all. Every was unusual. The fate most likely to befall a pirate was capture, trial, and death by hanging, it seems. 

This is the fate that met several of those active in the 1710s and 1720s. Woodes Rogers, who we met earlier, was active as a privateer during Queen Anne’s War, but instead of turning himself to piracy, he returned to his former life, and later sought the employment of the state. When the pirates of Nassau became too much of a nuisance, he formed an expedition to rid the Caribbean of this scourge. Rogers embarked on a campaign to reclaim Nassau, asserting himself as governor of New Providence

His tactic was to use both carrot and stick. Pardons were offered to any pirate who promised to cease their destructive activity, and the noose was offered to those who refused the pardon. Some, like Jack Rackham, took the pardon but returned to their old ways. Some, like Benjamin Hornigold, became themselves pirate hunters. Others met their fate in battle. Blackbeard was killed in an engagement with the crew of Robert Maynard, who had been sent to hunt down the fearsome pirates. Blackbeard was killed aboard the Lieutenant’s ship, becoming the focus of his adversaries and receiving a series of deadly cuts and shots.

Capture of the Pirate, Blackbeard, 1718, by Jean Leon Gerome Ferris (1920)

One of the biggest killers at that time, however, was disease and accidents at sea. A sailor was as liable to die of some fever, or scurvy, as they were of falling from the rigging, or drowning overboard — during storms and otherwise. Wounds inflicted by accidents or in battle could easily become infected. The shadow of death was everywhere — sailors would joke about being visited by ‘Captain Death’. And, of course, burials took on their own significance at sea. It may well have been preferable for sailors to be buried on land, but this wasn’t always possible. Many were committed to the deep, wrapped up in blankets or hammocks, with round shot secured to their feet to drag them to the depths. In so doing, many sailors became food for the creatures of the deep, unceremoniously finding their bodies ripped apart by sharks who had been attracted to the ship.

Perhaps you don’t want to be a pirate after all.

You Better Get Ship-Shape

If you want to read more about the pirates mentioned here, and more besides — if you want to know more about Morgan’s attack on Panama, Dampier’s travels, or Blackbeard’s blockade of Charleston — then you can find out more in these books. This list is not exhaustive — far from it — but it is a good place to start.

David Cordingly, Life Among the Pirates (1995)

Colin Woodard, The Republic of Pirates (2014)

Joel Baer, Pirates of the British Isles (2005)

Diana & Michael Preston, A Pirate of Exquisite Mind (2005)

Marcus Rediker, Between the Devil and the Deep Blue Sea (1987)

Have you got any more that you would recommend? Let me know.


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