Henry Avery and the Greatest Pirate Raid in History
Update: 2025-03-18
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On September 7, 1695, English pirate Henry Avery led one of the most daring pirate attacks - and most lucrative - in history. And to top it all off - he got away with it.
Sources
Wikipedia: https://en.wikipedia.org/wiki/Henry_Every
"Enemy of all Mankind" by Steven Johnson
Image: https://commons.wikimedia.org/wiki/File:Henry_Every.gif
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Transcript
00:00:00
On September 7th, 1695, English pirate Henry Avery would lead an attack taking one of the largest scores in human history.
00:00:11
This is the legend of Henry Avery.
00:00:18
Hello, and welcome to History Dispatches.
00:00:26
My name is Matt Brain, and I am here with my son, McKinley.
00:00:29
Do more handsome of the duo.
00:00:33
On History Dispatches, we like to talk about fun history stuff.
00:00:38
It can be kind of weird, it can be kind of wacky, it can be stuff we find kind of cool.
00:00:43
And you know what we find really cool parts of us?
00:00:46
Yes, we love pirates.
00:00:47
I've always loved pirates, my son has always loved pirates, so you take it away McKinley.
00:00:53
This is your show.
00:00:54
Thank you.
00:00:55
Who doesn't love a good pirates?
00:00:56
I've always loved that classic age of sale, high seas, kind of movies, Arrow, Flynn, and Captain Blood in the Seahawk or two of my favorite of the old classic action movies.
00:01:07
And it's always just drawn me in.
00:01:09
One of my favorite action movies is Pirates the Caribbean, the first one.
00:01:13
First one, yeah.
00:01:14
I mean, I love pirates.
00:01:15
I know I shouldn't, they're horrible, but they're just, I just love it.
00:01:21
And I will say that I am the same way.
00:01:24
You learn that from me, you know, you watched those Arrow Flynn movies, a million times with me as well.
00:01:30
Oh yeah.
00:01:31
And we'll talk about that.
00:01:33
Maybe we shouldn't reveal them quite as much as we do later down, but Henry Avery, he's not quite as well-remembered as he should be today.
00:01:41
He's been superseded by people like Blackbeard and Captain Kid and stuff like that.
00:01:47
But he probably had the most impact on pirate and even maritime history of any pirate in history.
00:01:54
And despite that, we know almost nothing about his early life, even his name is a mystery.
00:01:59
He's gone by Benjamin Bridgman, Long Ben, Jack Avery is spelled with an A or an E, and we only have a single piece of writing confirmed to be from him.
00:02:11
Our best guess is that he was born on August 20th, 1659 in Devonshire, England.
00:02:17
And as a young man, he may have joined the Royal Navy.
00:02:19
We don't know for how long what rank he was, what he did, but he's probably served there because he had such skill and he seemed to be very good on the water.
00:02:29
But his first kind of foray onto the history scene comes in 1693 when he took up career as a slave trader.
00:02:37
As I said, pirates are not nice people, not good.
00:02:41
And he made a reputation as not he wasn't a pirate at this time, but he was quick.
00:02:47
He was agile.
00:02:48
He was smaller.
00:02:49
He worked outside of the Royal Africa Company's monopoly on the slave trade.
00:02:53
And so while he wasn't doing anything illegal, he was certainly known to ruffle some feathers.
00:02:59
Because of this reputation, he was recruited in August of 1693 to be part of a venture called the Spanish expedition shipping.
00:03:07
This was under charter from the King of Spain to get sunken treasure ships.
00:03:11
It was basically a chartered expedition from the Spanish government.
00:03:16
So this was all above board to trade and salvage sunken ships in the Caribbean.
00:03:21
Okay.
00:03:22
So it wasn't actually a pirate op, not at all.
00:03:25
It wasn't even a British operation.
00:03:26
It was completely British fleet, but it was chartered by the King of Spain.
00:03:32
And Avery was recruited to be the first mate of the expedition's flagship, a new vessel called Charles II named in honor of the king.
00:03:40
It was built specifically for this expedition.
00:03:43
It was a 46 gun frigate, and it was known as one of the fastest ships ever built at the time.
00:03:50
It was one of the fastest ships on the water.
00:03:52
Avery himself, he was a to just paint you a picture.
00:03:55
He was tall.
00:03:56
He was good looking.
00:03:57
He had supposedly gray eyes, wore a light powdered wig.
00:04:01
And he would have made quite the sight.
00:04:02
He was an imposing figure and coupled with his experience in the Navy in slave trading and then being a charismatic fellow.
00:04:10
That's probably why he got this first mate position.
00:04:13
Now, the expedition's first stop was in Agcaruña, Spain.
00:04:18
This is supposed to take a couple of days to secure the last bits of paperwork, dot the eyes and cross the tees to make sure everything was above board.
00:04:25
And then they'd be on their way to the Caribbean.
00:04:27
But they ended up taking five months in Spain.
00:04:30
You gotta love it.
00:04:31
Gotta love paperwork.
00:04:32
You gotta love paperwork.
00:04:33
You'reocracy rules.
00:04:34
Yup.
00:04:35
And not only was it there for five months, but there was no word of when they were gonna get out of there.
00:04:42
Imagine sleeping in cramped nasty quarters on these ships.
00:04:46
The only thing to do was drink and gamble and less and less hope that this venture was gonna do anything.
00:04:53
And then a rumor started that they were going to get sold into slavery by the Spanish.
00:04:58
Oh great.
00:04:59
Now this rumor is almost certainly completely ridiculous.
00:05:02
But when the rumor spreads, people get nervous.
00:05:06
And so they were getting fed up and ready to do something.
00:05:10
The expedition was known.
00:05:12
It was actually paying quite well.
00:05:14
And so everyone here thought they were getting a big payday.
00:05:16
And when they're just sitting there not getting money, not doing anything, they're fed up and ready to do something.
00:05:22
And so Henry Avery, he planned a mutiny.
00:05:25
You gotta remember the risk of a mutiny in this time period.
00:05:29
If you succeeded, you became wanted criminals with basically no hope of returning to any sort of normal life.
00:05:35
It was either death by sea or death in the gallows.
00:05:39
And if you failed, you were caught, declared a criminal and also sent to the gallows.
00:05:43
So it was a huge gamble to do this because even if you succeeded, who knows how long you're actually gonna be able to stay sailing for.
00:05:52
But for whatever reason, they decided to go for it.
00:05:55
And on the night of May 7th, 1694, the mutinyers they gathered up.
00:06:00
The captain of the Charles II, the guy named Gibson, he was below deck from a sea sickness.
00:06:06
From there, Avery was able to quickly take command of the ship.
00:06:09
Mutinyers from other ships made their way to the Charles II and they started hauling everyone up.
00:06:16
And before long, they had all the mutinyers in one place.
00:06:19
Of course, the other ships realized what's going on.
00:06:22
And so they actually start firing on the Charles II.
00:06:25
Avery knowing his time is short.
00:06:27
He holds the loyal crew to Gibson at gunpoint, cuts the lines and they head out.
00:06:35
And more or less they made it.
00:06:36
At sea, the captain was very confused.
00:06:39
Remember, they were a lot faster than any of you.
00:06:40
Captain Gibson.
00:06:41
Captain, yeah.
00:06:42
At sea, Captain Gibson was very confused because he was below deck.
00:06:45
He was asleep for the whole thing.
00:06:47
The rest of the ships are too slow to catch up to the Charles II.
00:06:52
Gibson was sent back with 16 other crew and Avery was now in command of 80 sailors.
00:06:58
The Charles II was recristened to the fancy and Henry Avery was now a pirate.
00:07:04
So as pirates, the first thing you did was you established a code.
00:07:12
And the pirates code was actually a fairly universal document.
00:07:16
Pirates operate under a very weirdly progressive, though it wasn't.
00:07:21
They weren't trying to be progressive at the time form of democracy.
00:07:25
The role of captain was elected.
00:07:28
Everyone got an equal share of treasure and the captain and quartermaster would get two shares of treasure.
00:07:33
So it was surprisingly egalitarian.
00:07:36
So the code they talk about in Pirates of the Caribbean was a real thing?
00:07:40
On ironically, yes.
00:07:41
We don't have Avery's exact code, but we do have a code from just like 30 years prior.
00:07:46
And it sets forth things like if you get hurt and you take, let's say you lose a leg, you get an extra chunk of change in order to like get by or whatever.
00:07:57
And so they had a weird form of health insurance.
00:08:02
It was, like I said, surprisingly egalitarian.
00:08:05
And there were also like weirdly things like you couldn't have candles under the deck.
00:08:09
So it was also like, duh, but it was all, but like it was a weird, when you read a pirate code, it would be like, no man shall fall asleep on deck.
00:08:17
They'll be punished.
00:08:18
We elect our captain and no gambling past eight o'clock.
00:08:23
And it also guaranteed that everyone would get a vote.
00:08:25
And so pirate captains had to be good to their crew in order to stay in power.
00:08:30
It was very different from a merchant or especially a military ship where the captain was king.
00:08:36
Now the first and most pressing thing they needed was actually manpower.
00:08:39
They had 80 guys, but the ship required probably three times that in order to be like actually effective in combat.
00:08:46
And so they got their first taste of piracy when they raided three English merchant ships near the Cape Verde Islands.
00:08:52
And they took on nine new sailors, slowly but truly growing their ranks.
00:08:57
In addition, they stopped and they made modifications to the ship, making it even faster.
00:09:02
The biggest thing that it was you actually removed that the forecastle, and what this did is one, it streamlined the ship to make it even faster, but two, it fully made everything egalitarian because the captain slept with the crew,
00:09:14
okay.
00:09:15
And there wasn't a place that captain could go and hide and stuff like that.
00:09:18
So that part of pirates, the Caribbean is incorrect.
00:09:22
But now they had a choice.
00:09:23
They were at the crossroads of Africa, Europe, and the Americas.
00:09:26
And they'd actually decided to head south at the time.
00:09:29
The Indian Ocean was the main hotbed for piracy.
00:09:32
And so they decided to make the trip around the Cape of Good Hope.
00:09:37
We don't exactly know why they chose this.
00:09:40
But our best guess is that a few years prior, a pirate by the name of Thomas II, captain of the Amity, had at the time the largest treasure score in history, attacking the Mughals.
00:09:51
His exploits had made it back to England.
00:09:53
And there's some evidence that Avery and two actually knew each other, but they decided we're going to head south.
00:10:00
And now I do want to just take this aside and just say that as cool as these stories are, Henry Avery himself was a brutal individual.
00:10:09
He was extremely polite to other Englishmen.
00:10:13
But during his travel south of Africa, he raided a guineaine village and took on slaves.
00:10:18
They don't ever talk about what the slaves did on the ship, but you can't imagine it was anything very nice.
00:10:24
And so while he was polite and gentlemanly and many people liked him for that, he made his career in this slave trade and he was not a nice person to people outside of his command.
00:10:38
But they arrived in Madagascar in early 1695.
00:10:42
They had traveled 5,000 miles and their mission was to carry out the largest heist in history.
00:10:49
So I mentioned before that the Indian Ocean was a hotbed for piracy and the reason was because it had the evil, busiest and most lucrative trade routes in the world.
00:10:59
In particular, the Mughals, they were an Islamic empire that ruled most of India regularly made large pilgrimages to the Arabian Peninsula.
00:11:08
And so there's meant that there was tons of gold and spice and stuff like that constantly flowing in this area.
00:11:15
In Madagascar, Avery spent a couple of months, they repaired the ship, took on food and did some raiding actually in the French comoros, taking on more and more sailors and at this point he had over 150 men at his command.
00:11:28
After a few months, they decided to head north to the Red Sea and the plan was to wait for the Mughalships actually coming from Mecca back to India.
00:11:39
They knew they'd be loaded up with gold and jewels and essentially their goal was to wait for the Mughal treasure fleet, find the fattest one there,
00:11:50
attack and take it.
00:11:51
Not very complicated.
00:11:54
And as they made it to the island of param at the mouse of the Red Sea, something really kind of funny happened because Avery was not the only pirate who had this idea.
00:12:03
In fact, six ships had all converged on param independently.
00:12:08
Their goal was to attack the Mughal treasure fleet.
00:12:11
One of these ships was Captain by Thomas II and what I love about this is that they decided what's better than a pirate ship, a pirate fleet and they decided to team up and attack the Mughal fleet together.
00:12:27
Our good friend Henry Avery was actually elected as admiral of this fleet, which is interesting.
00:12:33
Thomas II and the Amity were actually there and he would have made probably a more logical choice because he had been raiding Mughals the previous few years.
00:12:41
But Avery was charismatic.
00:12:44
He had easily the best ship in the fleet and he seems to just have been able to convince people to do what he liked and so he was he got the command they elected him admiral.
00:12:54
He may have been in command, I love this fact, he may have been in command of as much a quarter of the world's active pirates at the time.
00:13:01
In 1720, so 30 years later, they said that there was about 2,000 active pirates in the world at the time, which is less than I would think.
00:13:11
But Henry Avery at this time commanded 440 men.
00:13:15
So if those numbers are correct, that means he would have had a massive population of pirates proportionally under his command.
00:13:23
They knew the Mughal fleet was coming from down the Red Sea across the Arabian Sea back to India, but their goal was no ordinary treasure ship.
00:13:31
But a vessel called the Gangessewai, or the Gunsway, and if they could take it, it would become the largest score in human history.
00:13:39
And so for a month, they remained on param, basically the baking in the summer heat until they almost made a catastrophic error when the treasure fleet slipped past param in the middle of the night.
00:13:51
I wonder if they knew that they were there or something because they almost lost it, right there.
00:13:56
And even with that hefty head start, Avery quickly gave orders, the slowest of the six pirate ships were scuttled, and her crew was taken aboard the fancy.
00:14:07
And then he actually towed the next slowest ship.
00:14:10
And yet even towing a ship, the fancy was still faster than any of the treasure fleet.
00:14:16
So much so that the other two ships actually fell behind.
00:14:19
But remember convoys at this time were not tight dense things.
00:14:24
People got spread out at night.
00:14:26
It was hard to see.
00:14:27
And so it's not surprising that Thomas II and the Amity actually had the first exchange of the battle.
00:14:34
And we're actually defeated.
00:14:36
They attacked one of the treasure ships called the Thoth Mahamandi.
00:14:39
And we're absolutely devastated.
00:14:42
Thomas II was killed.
00:14:43
The Amity was destroyed.
00:14:46
And Henry Avery didn't even know about this.
00:14:49
Because on September 7th, he caught his first sight of the treasure ships.
00:14:54
And it was actually the Thoth Mahamandi.
00:14:56
He was able to sneak up on her at dawn.
00:14:59
They fired a single broadside into her.
00:15:02
And she surrendered, which is kind of interesting.
00:15:04
They think that possibly she was damaged in the exchange with the Amity, but it was only here that he would have learned that Thomas II was dead.
00:15:14
And so he's basically on his own at this point.
00:15:17
And on the Thoth Mahamandi, they took 60,000 pounds worth of treasure.
00:15:22
And that's about $5 million today.
00:15:23
So this is no small score.
00:15:25
And they could have walked away.
00:15:27
But would you?
00:15:29
They knew that they knew that something's out there.
00:15:31
And you're in for a penny and for a pound, right?
00:15:35
And so they kept it up, pursuing the gunsway, and before it could make it back to India.
00:15:39
Remember, they're tracking her for days, you know what I mean?
00:15:42
And so they're just trying to catch up.
00:15:44
And their speed paid off and soon they were on the gunsway.
00:15:48
And I just wanted to describe to you this ship.
00:15:51
At the time, it was one of the biggest ships in the world.
00:15:53
It would have had hundreds of cannons, several decks high, so it was a tall ship, enough room for possibly a thousand passengers, hundreds of tons of treasure and dozens and dozens of muskets that you could shoot down onto lower ships with.
00:16:11
And so to attack the ship was insane.
00:16:14
But they went for it because they were able to get on her quickly and they fired one good broadside.
00:16:21
And this seems to have hit a powder magazine taking the ship out of commission, not allowing it to move.
00:16:26
And then they boarded.
00:16:28
Now there's two conflicting reports.
00:16:30
The English report says that the pirates stormed Aeroflin style and took the ship.
00:16:36
We're talking a couple hundred guys against hundreds of trained Mughal soldiers, maybe, maybe not.
00:16:42
The other story is from the Mughals themselves and actually from the captain.
00:16:46
And because of that, I'm inclined to believe him because he looks horrible in the story.
00:16:52
That's not normally how this thing goes.
00:16:54
And so as they were storming, he runs below deck, puts on a woman's disguise, and thus completely decapitating the command and Aeroflin is able to storm the ship very quickly.
00:17:06
In the report, he also says Aeroflin had twelve hundred men, which is absolutely not true, which is again, so he makes himself look good in one way.
00:17:14
And so I think there's actually a kernel of truth to that.
00:17:17
But either way, there's some fighting.
00:17:19
Several dozen Mughals are killed, apparently not a single pirate.
00:17:22
And Aeroflin takes the ship.
00:17:25
The guns way is his.
00:17:26
Now, two things happen.
00:17:29
One, we're going to go back to the elephant in the room, pirates not being good people.
00:17:33
There were several dozen women on board, mostly from actually the Mughals court.
00:17:37
And Aeroflin's troops proceed to commit apparently horrible sexual violence on them, just brutal.
00:17:44
The reports say that women were literally throwing themselves off the ship.
00:17:47
It was that bad.
00:17:49
So of course, all the reports also say that Aeroflin didn't participate.
00:17:52
Yeah, they always say that.
00:17:55
But either way, they made off with 600,000 pounds worth of gold in jewels, and that is over a hundred million dollars worth of stuff today.
00:18:07
It is still the largest heist ever conducted in human history.
00:18:13
Now Avery knows that they have to go.
00:18:16
They've just pissed off the Mughals.
00:18:18
They have the entire world at their backs.
00:18:21
And so they don't run all the way to Madagascar.
00:18:23
But they run all the way to the mahamas, specifically Nassau, which was known to host Shady Characters.
00:18:30
They get rid of the fancy because it's an obvious ship.
00:18:34
And they divide up the spoils.
00:18:36
And with that, the pirate career of Henry Avery is ended.
00:18:42
Dozens of crew went on to be found and captured, kind of all over, especially the American Seaboard.
00:18:48
And this is why we have so much testimony of these events because people told about it in court and stuff like that.
00:18:54
That Avery himself was never found, nor was his famous Mughal treasure.
00:19:01
It is still unfound, but he got it out of there because actually some of the coins on the ship were found in Providence, Rhode Island just a few years ago.
00:19:10
And more than just the heist, this legend made it everywhere.
00:19:15
He was the talk of the town in the 1690s.
00:19:19
There were so many legends that were based off of this, and you've probably heard some of them.
00:19:24
Supposedly he, in the Mughal Princess, they ran off to Madagascar and lived the rest of their lives in Paradise.
00:19:31
He founded the pirate colony of Libertalia, all those legends of Libertalia, the famous pirate haven stem from Henry Avery in this event.
00:19:39
But more than that, it was his kind of exploits and the newspaper stories and the books written about him.
00:19:47
Again, most of them not true, that inspired the next generation of pirates.
00:19:51
And it all kind of comes back to Henry Avery's incredible heist of the gunsway.
00:19:57
There's like two things that I love on this one.
00:20:00
You talk about describing the Mughal ships, and I remember doing some research on some of the great Chinese treasure ships of the 1400s and things,
00:20:12
and those are like that.
00:20:13
Their western ships were nothing compared to these things.
00:20:17
Tiny.
00:20:18
To actually have stopped one is just incredible, so again, and you point out that he had to have gotten lucky, hit the powder magazine.
00:20:26
One of the weird things about those ships is sometimes they were not necessarily designed that well in that they were deterrents in their size.
00:20:35
They were so big.
00:20:36
So when they actually got in the combat, they sometimes things like that happened where they were found susceptibility.
00:20:41
I also wonder that their captain sounds like a terrible commander.
00:20:45
And if they had a maybe the better guy in charge, they could have done a little better damage to Avery.
00:20:52
The other thing I love about Henry Avery is he scores big and he goes off and that's it.
00:20:58
I think one of the things I always find funny is a story of the person making one final big score doing this, you know,
00:21:08
the light before they retire.
00:21:11
He made his one big score and that was it.
00:21:12
And he was just like, no, I'm not interested in being pirates, but you know, and all those other ones that the pirates are like or the bad guys are like they love being pirates.
00:21:20
They don't really care about the treasure and so forth.
00:21:24
But here he just got his money landed and basically said, okay, guys, here's your, here's your loot.
00:21:29
Have a good time.
00:21:30
We really don't know what happened to him his last.
00:21:33
There's some legends of him living in like Ireland or back in Devon.
00:21:38
Some legends say that he spent all his money and lived the rest of his life as a popper.
00:21:42
But nothing is concrete.
00:21:44
There's no like good credible source for any of it.
00:21:47
So we have no idea what happened.
00:21:50
He literally could have so funny.
00:21:51
He could have just bought in a state in the mountains of Alps and just retired, you know, with that much money.
00:21:59
He could have done whatever he wanted and disappeared, you know, because no one's going to look him up on the internet in 1690 something.
00:22:06
And I mentioned that this was kind of sparked so much maritime history.
00:22:11
He sparked the first worldwide man hunt.
00:22:14
Oh nice.
00:22:15
The British government, the East India company and the Mughal Empire all had bounties out for him.
00:22:23
All had people.
00:22:24
I'm guessing Spain did too.
00:22:25
Probably.
00:22:27
But he literally sparked the first worldwide man hunt.
00:22:32
That's for him.
00:22:33
And he evaded it all.
00:22:34
I got to give him some credit.
00:22:36
Okay.
00:22:37
Well, this was a pirate story, which we always love and McKinley, thank you for for telling the story of Henry Avery, I think.
00:22:47
So I'm going to wrap up today by just saying, Hey, I hope you had a good time.
00:22:51
If you want to learn more about the show, go to our website history dispatches.com.
00:22:57
There you can find all sorts of stuff about the show, including listening to other episodes.
00:23:01
So again, thank you for listening McKinley.
00:23:04
Thank you again for leading things today.
00:23:06
Thank you very much.
00:23:07
All ready.
00:23:08
Good day everyone.
00:23:11
(electronic beeping)
00:23:14
