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Piracy has a longer, more interesting history than you may assume, as this literary collection clearly demonstrates

Think of the word “pirate” and give yourself a moment to sit with the images that come to mind. You likely drew from a handful of cultural touchstones embedded in our individual and collective consciousness, set there by the mass marketing of the Golden Age of Piracy. The Jolly Roger. Buried treasure. A plank waiting for someone to walk it.

The Golden Age of Piracy lasted from 1650 to 1720. Now it lives on in caricature. Piracy as an undertaking, however, is much older. With its origins in Classical Antiquity, pirates have raided and plundered throughout the world, cast as heroes, villains, honourable folks making a living, bottom feeders destroying the livings of others, state liabilities, and state assets. Piracy is multidimensional, as are the men and women who have come comprise its legends – along with the fact and fiction that make it evocative, fascinating, and fun.

In Pirates: A New History from Vikings to Somali Raiders (Yale, 2019), Peter Lehr traces the origins of piracy and the forces – push and pull, as he calls them – that have driven people to take up the life. Dispelling the Hollywood myths about the profession, he argues “piracy was not so much about romanticism and adventure as about greed and grievance, with some measure of creed or religion thrown into the mix.”

In the past, as the present, poverty, a lack of better options, and weak or non-existent state institutions shaped the choice as well. “In essence, what made individuals become pirates was an exercise in rational choice that included factors such as current living conditions, expected returns from piracy, and the probability of getting away with it.” Thus pirates, typically poor and alienated individuals, were pushed and pulled into “A merry life and a short one,” as Bartholomew Roberts, one of the most successful pirates of all time, put it.

While piracy could be a private career of risk and reward for oneself, for some it was state-sanctioned. Pirates who undertook the life in service of the state were known as privateers, carrying out raids and plunder against enemies of the flag they flew. Sir Francis Drake was one of them. In The Secret Voyage of Sir Francis Drake (Douglas & McIntyre, 2013), Samuel Bawlf attempts to unravel the mystery of Drake’s 40,000-mile voyage around the world from 1577 to 1580 which included, among other endeavours, a search for the Northwest Passage through lands many Canadians will be familiar with.

Bawlf’s volume is a detailed, gripping account of Drake’s trip on the Golden Hinde. Capturing the allure and the brutality of the endeavour, the book walks the line between the swashbuckling tropes that make up contemporary understandings of pirates – and privateers – and the harsh reality of what their activities entailed.

The historical record in text that Bawlf draws on is one source of knowledge about the history of piracy. Another is artifacts. Plenty of items remain, tucked away in museums and private collections, but the greatest piracy artifacts of them all — ships — are notoriously rare and hard to find. To date, for instance, only a handful of Golden Age pirate ships have been discovered and identified.

In Pirate Hunters (Random House, 2015), Robert Kurson tells the story of the search for one of them, Joseph Bannister’s the Golden Fleece. As the book’s protagonists, John Chatterton and John Mattera, set off to the Dominican Republic in search of Bannister — a gentleman member of the British Navy turned pirate — and his ship, their pursuit soon comes to read like historical mystery and contemporary thriller.

One of the few books that deserves to be classified as impossible to put down, Kurson’s pacing along with Chatterton and Mattera’s skills and passion, make for a story that ought to come with a warning: It will make you want to quit your job and set out to discover something, anything, beyond the horizon of your current life. And why not? Recalling one of Chatterton’s life rules, “Do it now. Tomorrow is promised to no one,” there are worse risks to take.

Both historically and today, piracy has been dominated by men. But not exclusively. Anne Bonny is one of the most remarkable figures in pirate history, matched if not exceeded by Zheng Yi Sao, who commanded a fleet of hundreds of ships and tens of thousands of men. In Pirate Women (Chicago Review Press, 2019), Laura Sook Duncombe chronicles the lives of these women and others whose stories are often ignored or marginalized. Part of understanding the layers of pirate history require a more thorough accounting of the era, and Sook Duncombe does just that.

Reconceptualizing pirates as a theme and opening it up requires non-fiction and fiction to clear space in our imaginations. A YA novel is a good tool for just that. Tricia Levenseller’s Daughter of the Pirate King (Square Fish, 2017) introduces us to the young Alosa Kalligan, captain and commander, on the search for a map that will lead to a great fortune. “I hate having to dress like a man,” the book opens. Alosa laments the disguise, a ruse designed to get her captured in the service of the search. “The clothing is awkward as it hangs lose in all the wrong places. And the smell! You’d think men did nothing but roll around in dead fish guts while smearing their own excrement on their sleeves.” A duology, Alosa returns in Daughter of the Siren Queen. She’s a character whose story you wish to follow, as you would Blackbeard’s, Anne Bonny’s, or Captain Kidd’s.

The romanticism of the dramatized pirate life is compelling and enjoyable. The historical stuff is no less of a draw, even if it bumps up against fiction we take for fact. A wide and growing range of books is opening the world to new perspectives, stories, and characters. If you decide to embark on a journey through these stories, do yourself a favour and don’t just stick too close to the shores of familiar fodder. There is treasure beyond Treasure Island.

Pairing suggestions

Food and drink

Pirate food is … not distinguished. Nor is scurvy. But pirate drinks range from rum to things with rum in it, and you can do a lot with that – including grog, one manifestation of which is a cocktail including dark rum, sugar, lime juice, and water. But nothing beats a whisky aged in rum casks. Or pirate whisky, if you will. Two of the best on offer are The Balvenie’s 14-year Caribbean Cask and Glenfiddich’s 21-year Gran Reserva. The bad news is you may have to plunder a few ships to afford them, especially the latter.


A study of relationships and identity set in the Golden Age of Piracy, Our Flag Means Death draws on real-life characters including Edward Teach — better known as Blackbeard — and the gentleman pirate Stede Bonnet. It’s fun. It’s funny. It’s charming. It’s got gay pirates. The first season is available now on Crave.


The greatest pirate game of all time is probably Sid Meier’s Pirates! From the creator of the Civilization series — the latest entry of which, Civilization 6, may have occupied several thousand hours of this writer’s life — the 2004 game finds you building a pirate empire on land and at sea. It has dancing, courting, and sword fights. Available across platforms and on Steam, the game holds up well and rounds out any proper pirate deep dive.

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