The “Golden Age of Piracy” was surprisingly egalitarian. But did buccaneers make more than today’s NFL players?
Few careers have been more romanticized than piracy.
Pirates spent — and often lost — their lives chasing it. Shoulder parrots squawked about it. Treasure maps pointed to it. Her Majesty’s navy spent decades trying to keep it.
But was it actually a good gig? Could a smelly 17th-century buccaneer sailing out of Port Royal really out-earn a modern-day quarterback?
I co-wrote this quirky issue with my friend Michael Patchen, who has the excellent newsletter MoneyLemma.
About half of the original issue is intact, but I’ve added some of my own context, commentary, and updated data.
This is not a pure repost. Think of it as a remix — the newsletter equivalent of a quote tweet or a TikTok duet.
Let’s set sail 👇
MoneyLemma is a hedge fund analyst who delves into pressing, unanswered questions in the overlaps between money and society. Previous guest posts include Is America at Peak Vending Machine? and The Traffic Ticket Industrial Complex.
Table of Contents
Why 17th century pirates?
As long as there have been boats, there have been pirates robbing them. Julius Caesar, Christopher Columbus, and Tom Hanks have all been pirate captives at one point (for Tom Hanks, it was just two hours during Captain Phillips).
But this issue focuses on 17th-century Caribbean pirates. Why? Two reasons.
First, this was literally the golden age of piracy. Merchant ships were ferrying gold, silver, sugar, and spices back to the Old World — perfect targets for plunder.
Second, we actually have real economic data from this period, thanks in large part to a 500-page nonfiction tome by Daniel Defoe. Yes, that Daniel Defoe — the author of Robinson Crusoe. That story was inspired by real-life pirate Alexander Selkirk, and Defoe’s obsession with piracy ran deep.
Pirates of this generation were known as buccaneers (a term derived from the jerky they used to eat). They came from everywhere: former privateers backed by monarchs, runaway slaves, navy deserters, dumped convicts, and all sorts of misfits.
In a way, they were the counterculture of the era. Much like the LSD-fueled movements of the 1960s (which we recently covered in Investing in Psychedelic Posters, and Michael covered in this great piece), pirates rejected the systems that rejected them. They stole from the rich, lived freely, and answered to no one.
They also, let’s be clear, murdered families, sacked entire cities, and were truly disgusting, unbathed people. Still, like mobsters, gangsters, and Kardashians, we often overlook the awful stuff and romanticize the lifestyle.
The economics of piracy
Quick disclaimer: Translating 17th-century currency into modern dollars is tricky! Values were volatile, and there was no central bank to anchor purchasing power. But we’ll do our best to stay consistent using historical economic estimates.
Today, you might call buccaneers libertarian-socialists. Libertarian, because these pirates were rugged individualists who held freedom above all else. As Bartholomew Roberts — aka Black Bart, who captured over 400 ships — once put it:
“In an honest service there is thin commons, low wages, and hard labor; in this [piracy], plenty and satiety, pleasure and ease, liberty and power. A merry life and a short one shall be my motto.”
At the same time, these people were socialists. On and off the ship, they shared everything. Early buccaneers lived in bands of six or eight that operated like deranged hippie communes.
Profit sharing
This strange philosophical mix transferred to the economics of the business. Pirates were entrepreneurs who banded together for joint ventures — the venture being to plunder as many ships as possible. A group of (typically under 250) crewmates would democratically elect a captain to make strategic decisions like which vessels to target.
The captain’s authority was limited and revocable. Pirate crews could — and frequently did — vote to depose a captain mid-expedition. Once the plundering was done (or everyone was dead), the venture dissolved, and profits were split almost evenly among the crew.
Captains and quartermasters received double shares, but that was about the extent of hierarchy.
In this way, pirate ships were essentially employee-owned businesses!
Low expenses
Pirating operations had few upfront expenses. After all, ships were rarely purchased — they were stolen. Early buccaneers often hollowed out tree trunks into canoes and rowed out to hijack their first real vessel. They packed jerky, barrels of water, and rum, then took to the sea.
In terms of ongoing costs, again, not much. No fuel. No port fees (I mean, they killed anyone who tried to charge one). They stole all their supplies, repaired their own ships, hunted food, and found fresh water.
Occasionally, pirates would buy food, bribe officials, or pay for medicine, but most costs were covered through theft.
That said, Pirate Code — a general set of rules that evolved over time — did stipulate some required expenses. Crew members who lost a limb, an eye, or another body part were paid a one-time stipend.
Because expenses were so low, ships could be self-sustaining for years — even building up into small armadas of stolen vessels, many manned by captured prisoners.
Pirate governance was shockingly progressive
While pirate crews were often violent and disorderly, their internal governance systems were surprisingly structured — even progressive by the standards of the 1600s.
Most ships operated under Articles of Agreement — written constitutions that every crew member signed before setting sail.
They outlined:
- Loot-sharing rules (how the booty was split)
- Conduct expectations (there were strict rules against gambling, brawling, or murdering other crewmates, but duels were allowed)
- Injury compensation (for example, losing a right arm was worth 600 pieces of eight, or about $60,000 today.)
- Procedures for electing or deposing captains. (Incredibly, crew members had the right to vote out their captain if they felt leadership was unfair or ineffective)
“Every man had a vote in affairs of moment; the captain and quartermaster received two shares of a prize; the master, boatswain, and gunner, one and a half; other officers one and a quarter.”
— New England Pirate Museum: Articles of Agreement
In some ways, pirate ships resembled early worker co-ops more than naval vessels. You didn’t just take orders; you had a voice, a vote, and a financial stake.
They were violent, chaotic, and anarchic. But in terms of labor equity, pirates ran one of the most egalitarian businesses the world had ever seen.
Pirate revenues & distribution
The revenue of a pirate ship was simple: however much loot they could plunder. But the outcomes were wildly inconsistent.
Some expeditions ended in total failure. Ships were sunk or captured before ever landing a score. On the flip side, some pirates struck gold — literally.
- In 1672, Captain Laurens de Graaf intercepted a Spanish merchant ship and seized 120,000 pesos — worth an estimated $12 million today. But even he wouldn’t see a haul like that again for another decade.
- Captain Henry Morgan once returned to port with 500,000 pieces of eight — roughly $50 million in today’s money. And that haul doesn’t even account for barrels of stolen wheat, rum, and other trade goods filling the hold.
But those were the outliers. Most captures involved far more modest bounties — grain, furs, textiles, or dried meat.
Historical records from the late 1600s suggest that, across the full lifetime of a venture, pirate ships tended to do pretty well.
- Low end: Some expeditions yielded barely anything. Captain Morgan’s Panama raid (1671) reportedly paid just $20,000 per pirate, in modern dollars.
- Median case: A well-run raid could net a pirate $60,000–$80,000, assuming modest cargo and a standard crew size.
- High end: The Cabo Verde expedition paid each crewmate 4,000 British pounds plus 42 diamonds — worth over $1.2 million per pirate today.
One robust report estimated that a typical successful venture yielded the modern equivalent of ~$5-12m per venture, or ~$3 to $8 million per successful venture.
And because expenses were minimal and loot was split fairly evenly, a successful expedition could lead to a serious payday for every crewmate.
How much did the median pirate actually make?
Key assumptions (in today’s USD)
First, we need to establish our assumptions.
- Crew size: ~100 pirates per ship for modeling “median” cases
- Loot per successful raid: ~$5-$12 million per raid. Let’s call it $8.5m
- Success rate: 60%
- Loot per raid (overall): ~$3-$8 million per raid. Let’s call it $5.5m
- Raid frequency: 1.5 raids/year for active pirate ships
- Loot per year: $8.25m per ship per year
- Captain’s share: Double (2% of loot)
- Pirates’ share: Split evenly
Expected value per pirate
Now we calculate expected value per pirate.
Let’s say the average ship yields $8.25m per year. The captain’s double take means he gets $165,000, leaving $8.1m for the rest of the crew.
Divide that among 99 pirates, and you get $81,666 per pirate per year.
Not a bad payday! Especially in an era without taxes. Though not exactly enough to buy your own Caribbean island.
Externalities (uncounted)
However, this doesn’t account for casualties or lost future earnings.
- Most pirates didn’t last long enough to get rich, because disease was a constant threat. Scurvy, dysentery, yellow fever, and tropical infections routinely swept through crews. Mortality rates from disease alone reached up to 50% of men per year!
- And then there was combat. Pirates routinely clashed with armed men or military convoys. Many battles cost crews 10–30% of their men in a single engagement.
If 30% of the crew die or are captured per year, the adjusted expected value falls substantially.
Let’s assign a crude “human cost” of death or capture: say, –$500,000 in lost lifetime earnings per person.
Adjusted EV:
- Expected income (70% survival chance): $57,166
- Expected loss from death/capture (30% chance): –$150,000
- Net expected value per pirate, per year: –$92,834!
Once you account for failure rates, death, disease, capture, and expeditions that ended with nothing, the “expected value” of piracy drops a lot.
So even though the average payday looked promising, the expected value after risk was negative for most pirates — unless they survived multiple raids without injury.
Pirates vs NFL players: Career earnings comparison
In this version, I estimated how much money each group made over the course of their careers.
- NFL players: Median salary of $860,000 per year, multiplied by the average NFL career length of 3.3 years
- Pirates: Estimated lifetime hauls based on historical case studies, then scaled to modern dollars
For example:
- A “median” pirate might participate in 3 successful raids over a short 2–3 year career, earning ~$81,666 per raid. That’s a career total of ~$204,165.
- Meanwhile, the NFL median player earns ~$2.8 million over their career.
Here’s what that looks like:
Closing thoughts
So there you have it folks. Being a pirate may have been exciting, but it was nowhere near as lucrative as being an NFL player.
The average pirate earned enough to live well for a short time, but not enough to build lasting wealth.And when you account for the potential loss of life, it wasn’t a great investment at all.
But for me, it was interesting to learn that pirate ships were collectively owned. The crew shared almost everything and kept nearly all of the profits.
Contrast that with the NFL. The Dallas Cowboys generated $425 million in profit last year, while players received about $180 million. If the Cowboys operated like a pirate ship, players and staff would actually triple their income!
As always, the real treasure isn’t just the loot. It’s the structure. Ownership, more than anything, determines who ends up rich and who ends up cannon fodder. 🦜
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That’s it for today!
A huge thanks to Michael Patchen for helping with this guest post. For more check out his excellent Substack, MoneyLemma.
See you next time,
Stefan
Disclosures
- This issue was originally written by Michael Patchen, with new sections and significant editing from Stefan von Imhof
- This issue was sponsored by FranShares
- Altea has no holdings in any companies mentioned in this issue.
- This issue contains no affiliate links.
