Katie Charlewood (3:40)

What kind of pirate are you? The swashbuckling one or the one who burns DVDs? Oh, if you're so young that you don't know what burning a CD is. Oh, that may be another history lesson that I'll just have to do at some point. But yeah, I, I was like pirates because I want to do something a little bit more fun. She says about, like, horrible stuff. Because this time of year, especially this time of year, can be really hard for a lot of people. It can be really difficult, um, especially if you're neurodivergent. So if you're neurodivergent, you are affected more on big days, um, not just because of the what goes up must come down scenario, but these big days, like big events, high holidays, whatever, they can like, really, really affect your regulation and whatnot. Like your ADHD symptoms. It's like they're turned up to 11 this time of year. And on top of this, typically people are more likely to suffer anxious or depressive episodes during the festive period. And so I'm like pirates. That being said, I am going to be talking about raiders, marauders, pillagers, plundering, murdering, torture.

Katie Charlewood (5:01)

Robbing, stealing, slavery, colonialism and just a whole lot of crime. So if you have an issue with any of those, I'm going to suggest you exit stage left and I will see you in like, two episodes. But I know what you're thinking. You're thinking, katie, it has been over 3 minutes. Please quit your jibber jabber and fact me and fact you, I will. But first we've got to get our source on.

Katie Charlewood (5:32)

Our sources are.

Katie Charlewood (5:34)

Privateers and Pirates of the West Indies by Violet Barbour, Pirates of the Original Panama Canal by Samir S. Pannell, Piracy and the Laird Sovereignty of the 18th century Atlantic by Mark Shark, Pirates of the West Indies by Clinton V. Black.

Katie Charlewood (5:56)

Piracy and History by Adlari Morali Buccaneers of the How Piracy Forged an Empire by John Latimer Modern Scholarship in Caribbean Pirates, 1650-1725 by Larry Schweikat and B.R. berg.

Katie Charlewood (6:17)

Sir Thomas Modiford by Noalla Zahidia.

Katie Charlewood (6:25)

Henry Morgan by David Williams.

Katie Charlewood (6:31)

Jamaica Gleaner Pieces of the Past Henry Morgan, the Pirate King by Rebecca Tortello.

Katie Charlewood (6:39)

The Buccaneer King the Story of Captain Henry Morgan by Graham Thomas.

Katie Charlewood (6:47)

Pirates, Brigands, Buccaneers and Privateers in Fact, Fiction and Legend by John Rogozinski.

Katie Charlewood (6:57)

The History of Piracy by Philip Gosse.

Katie Charlewood (7:03)

Iberia and the Culture, Politics and History by John Michael Francis.

Katie Charlewood (7:12)

Buccaneer Admiral Sir Henry Morgan by H.R. allen.

Katie Charlewood (7:18)

Admiral Sir Henry Morgan, the Greatest Buccaneer of Them all by Terry Breverton the Buccaneers of America A true account of the most remarkable assaults committed of late years upon the coasts of the West Indies by the Buccaneers of Jamaica and Tortuga by John Exomellon I've definitely mispronounced his name and of course we have our old favourites, history.com and biography.com.

Katie Charlewood (7:48)

Well, I use it in comfortably. Good. Then let's begin. Captain Morgan, more than just a rum he was a real person from Wales of all places. So Wales is a country that's sort of on the side of England and it's. It's part of Britain and the uk, but it is also its own country. Listen.

Katie Charlewood (8:15)

Geography is political and it's also weird. Anyway, so Henry, or as he was originally Harry Morgan, was born around 1635 in either Pencarn or Llan Romney in Wales, basically one of these two towns which is between Cardiff and Newport. So his father, he's a successful farmer and naturally it was assumed that he would follow in his father's footsteps, but alas, Harry had other plans. He ends up moving to Bristol, which I have mentioned in previous episodes that Bristol was a port town and Bristol is fairly close to Cardiff. So like once you get there, you're just like a hop, skip and a jump away, like they're really, really close. And so Henry, Harry, he is seeking adventure, right? So his uncle, I believe is some kind of seaman, I'm not sure which type, but at that point he's some something to do with a man on the sea. And Henry here, he's seeking adventure and so he makes his way to Bristol for exciting employment opportunities and he reaches the docks, he manages to make his way from Bristol to Barbados. Now, I don't think I mentioned that this time about Bristol, as it's actually an English town, so it's an English port town. It's just across from, like, Cardiff in Wales. Two separate countries. They are part of another. It's a thing. So, yes, you have Bristol to Barbados. How? I mean, logically, one would assume he either joined a crew or he stowed away, or perhaps he just tied an inflatable banana to the back of a ship and hoped for the best. Nyet, my friends, nyet. So there are two main theories, because we don't actually know exactly how he got there. Right. The first theory being that he traveled to the Caribbean as part of Robert Venable's army. Like, they were being sent over there as part of the Caribbean expedition against the Spanish by Oliver Cromwell. I know that I discussed this, actually Oliver Cromwell and the whole monarchy situation in several episodes. I think it's in some of the witch episodes. And I know I talked about it in the Barbara Palmer episode, so I will probably just do an episode on Cromwell at some point. That day is not today, though, because why would I speak about a man if I don't have to? I say that as if I'm not talking about Captain Morgan today. But, like. Like, I mean, I have so many pirates, I've got to talk about some of the male ones. Right. Anyway. Right. It's equality. Right. It's fair.

Katie Charlewood (11:24)

So the other theory as to how Henry Morgan got to the Caribbean was that he was taken to Barbados as crew and then sold on as a servant.

Katie Charlewood (11:37)

Neither is verified. Right. For the record now, traveling on the ship and then becoming a servant on the other side, that's indentured servitude. It was a way that a lot of people actually got to the New World. So someone would pay their passage and their passage would result in them, like, working on the other side. And then they would work off so many years, and they're, like, basically paying off a debt effectively.

Katie Charlewood (12:08)

So you could work your way out of indentured servitude, you could not work your way out of slavery. I just want to confirm this for the people who might not know that. And again, I feel like I've discussed this many times before. It's just a lot of history repeating.

Katie Charlewood (12:29)

So when he's in Barbados, he does join Robert Venable's army. And it's from this military service that Henry Morgan finds himself in the world of piracy and privateering. And this is around the 1650s, which is like the beginning of the golden age of piracy. Now, the golden age of piracy lasted between, like, 1650 and 17. 1720, maybe 1730. 1730 actually, yeah, because it's 80 years in total and not that long in the grand scheme of things, but it's a good chunk of time, this 80 year period. And the golden age of piracy itself is split into three periods. You've got the buccaneering period, you've got the pirate round and then you've got the post Spanish succession period. I'm going to cover this thing a little bit now, but I think I'm going to go do a deep dive in another episode. I think yeah, you deserve that because there's a lot there. So the buccaneering period is the first period and this is from about 1650 to 1680, which 30 years, which, you know, fairly decent. And this occurred typically around Jamaica and Tortuga. And this was between the English and French seamen against Spanish ships, settlements and colonies.

Katie Charlewood (14:07)

Why the buccaneering period? Well, it's region specific. So buccaneer relates to.

Katie Charlewood (14:17)

Pirates in the Caribbean and the west coast of Central America. And the word buccaneer actually comes from the French boucan because English is four languages and a trench coat. So boucain was a grill for smoking meat and it was basically making jerky. It made jerky. So French wild game hunters, they would use the boucain on the Caribbean island of Hispaniola, which is now Haiti and the Dominican Republic, because again, remember, geography is political. So originally the term applied to these French hunters who weren't exactly welcome on the Spanish controlled island of Hispaniola. So these huntles, like they mainly survived by hunting game from native species like the hutia and, and game introduced by the Spanish oxen, boar, cows, actual cows. Like that's so many cows. Spain brought cows. But yeah, so there's hunting game. But in addition they are also pillaging Spanish ships around the coast of the island cuz, you know, finite sources.

Katie Charlewood (15:40)

Naturally the Spanish aren't too happy about that. And so they are trying to push the French game hunters out of Spanish territory. And as time goes on, unscrupulous members join these hunters along with some ne' er do wells, you might say, possibly scoundrels and scallywags. And this is not making the Spanish happy. Now the Spanish are all over the Caribbean, right? They have made many settlements and they have like really dug, you know, their, their heels in here. And so the Spanish are making life a bit more difficult, you know, for the buccaneers. And so these groups start fighting back and start pillaging more Spanish ships. And as these buccaneer groups got larger and you know, they sort of end up fleeing for another island just off the coast of Hispaniola, which was also controlled by Spain, and one that you may have heard of, the island of Tortuga. Tortuga was a bit more defensible than the northwest of Hispaniola. So, like, because they were relegated to this island with little to no food sources, they really turned to piracy because, like, they didn't have things to hunt because they were kicked off this other island. I mean, yeah, it's like, effectively, how do I put this? Piracy is crime on water.

Katie Charlewood (17:19)

More specifically, the sea. I mean, I'll be honest with you, I'm not entirely sure that lake or river piracy is quite a thing. Like, does it stop when you get to an estuary? Like, where. Where does it stop being piracy? Is it only open water? That is. That is the question.

Katie Charlewood (17:41)

Someone will have that answer for me. Anywho, you've got buccaneers, you've got Corsair and privateers. Now, privateers are legal pirates. They have a letter of mark, which is a document that makes you a legal pirate. Robbery under arms was a thing anyway. Like, it was seen as acceptable to, like, loot during acts of war. Right. To the winner go the spoils. Right. Legal looting, if you will. Now, I'm not going to go into that right now. We're gonna. We're gonna deal with that later. But so a lot of countries, they used privateers because most of them either had, like, teeny tiny navies or no navies at all. And so they were able to outsource this so they could just hire these guys to be their little navy, you know, and all they had to do is be like, yeah, you can also steal whatever you want. I'm gonna touch on Corsairs, even though they're not, like, involved in this in any way. So the Corsairs, because they're mostly over in the Mediterranean, some were, like government sponsored, crown sponsored, some weren't. Like, they. They caused such a commotion that, like, entire wars would start because of them. And so you had, like, Turkish Corsairs, you had French Corsairs, like, a whole bunch of them. They were like a massive geopolitical headache. But we will discuss them at some point. But yes, back to Henry Morgan. And so, like, at this point, he's joined General Venable's British army in Barbados. And again, the reason this army was there was because Britain had put them together with the aim of invading Spanish territory in the West Indies. This army was 3,000 strong. So a fair few men when it sailed from England, a number that Tripled when it stopped in Barbados. Right.

Katie Charlewood (19:51)

So whether Henry Morgan was an original crew member or joined in Barbados, well, whoms to say, right, so.

Katie Charlewood (19:59)

It'S got 3,000 men at this point. It had a decent number to begin. I had a thousand, right, to start. Now it's got three. Like that's big at the best of times.

Katie Charlewood (20:10)

Now I'm not here to tell people how to run their dangerous colonial armies.

Katie Charlewood (20:19)

But perhaps it would have been a good idea to have a plan.

Katie Charlewood (20:25)

Because like Venables, he wasn't exactly given a target as such. Right. They more sort of floated the idea because some targets in the West Indies they were suggested, but they were basically given free reign to do whatever. During the Anglo Spanish War of 1645-1660.

Katie Charlewood (20:52)

There were many Anglo Spanish wars, like, like a whole chunk of them. So I will be being specific about specific wars, cuz there, there's a lot. If I miss one, I'm sorry, but there's, there's so many. Like when weren't the English sparring with another nation? Right, like there's many. Anywho, Venables, he decides that he's not going to do anything by halves and comes out all guns blazing and he decides that he's going to attack the island of Hispaniola, the island that has been under Spanish control for well over a century.

Katie Charlewood (21:31)

On a scale of zero to invading Russia in the winter, how bad is your idea? Okay, because this.

Katie Charlewood (21:42)

They.

Katie Charlewood (21:44)

This is. Oh my goodness. Unsurprisingly, this attempt to take Hispaniola was an absolute disaster.

Katie Charlewood (21:56)

Twice. That is to say he fucked up royally. Twice. Right. They had their arses handed to them both times. And in a move that surprised absolutely no one after the second defeat, Venables declared very loudly that his men were cowards. And he's like fuck this for game of soldiers and sets his sights on Jamaica instead. Right. He thought that if he could take Jamaica that it would be like a pretty sweet victory for the British as an alternative to Hispaniola. I would like to preface this by saying that I have nothing against Jamaica. I would love to visit Jamaica. So if you want to invite me, I would love to actually. Sidebar sidebar. So I discovered that you can prepay customs through the UK if you're sending packages to the, to the us right? And I, I live in a border county, so I am very close to the uk. I live in Ireland, but I'm literally across the border. So I was like, oh, let's do that. Because I have been having a fight with USPS for months. So I'm tracking the package, and for a week at least, it has been in a sorting office in Jamaica. I didn't know that a sorting office was in Jamaica because it's going to the US because it went to New York, then went to Jamaica. And I. I thought Jamaica was part of the Commonwealth. If it's not, again, geography, by the way. Not my strong point, by the way.

Katie Charlewood (23:45)

So I was like, where's it going? Is it going there? Is it not? Like, because it's supposed to be going to Los Angeles, and there was, like, tea and chocolate in it, and I've already had to replace the chocolate before because of a customs issue. And now I don't know if this Terry's Chocolate orange is gonna land there. Still spherical at this point. Like, I'm at the point where I'm gonna have to just travel over with a suitcase full of goodies, right? Just throw it in the window and go like, that's. That's my new plan, anyway. I didn't realize there'd be a sorting office in Jamaica is my whole thing. I was very surprised, and I actually now really want to see the Jamaican Sorting Office. I'm so. I'm such a weirdo. I'm like, ooh, I want to go see the sorting office. But anyway, Jamaica at this point in time, so we're talking mid 17th century, it is this underdeveloped island, like, compared to, like, Hispaniola. It had one town, just one, I'm serious. And it was defended by a grand total of 200 Spanish soldiers.

Instacart Advertiser (24:57)

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Katie Charlewood (24:57)

And again, to reiterate at this point in history, it wasn't really seen as a useful. Like, a useful island for the British and the Caribbean.

Katie Charlewood (25:09)

So Venables here, he just used a thousand men to capture an island. That wasn't significant at this point, right? At this point, no. Here's the thing. He had 3,000 men. There's a whole stuff happening. He marched them up to the top of the hill and he marched them down again. And then he had 1,000 men. Like, some deserted, some just, like, obviously were injured or killed. And, yeah, he's left with a thousand. And in that thousand, one of which is Henry Morgan.

Katie Charlewood (25:45)

So they take the island and the. The. Well.

Katie Charlewood (25:52)

The. The country, England, they are not impressed. Like, they thought that this was such a waste of manpower and resources, so that when General Venables returns to England, they threw him in the Tower of London, like, straight away. He was imprisoned for mishandling the army. Like, that's that's the whole thing. So while he's in the clink, like most of his troops, they're still in Jamaica, including Henry Morgan. And surprise, surprise, the Spanish were fighting back. Not, not very well, but they were. But it wasn't military maneuvers that were the greatest threat to the British troops. No, it was disease. So all of these tropical diseases, like there'll be English and Welsh bodies, they just couldn't handle it. Right. So you had yellow fever, was a major one. And another, of course, was dysentery, because all roads lead to dysentery. But Henry Morgan survived because otherwise this would be a much shorter story.

Katie Charlewood (27:13)

Jamaica eventually came under complete British control when the Spanish were pushed back. And this island was actually a good vantage point into the Caribbean for the British, even though it was initially seen as Venable's failure. Also, in addition. Furthermore, it led to a village with a fairly decent port being established, one of great interest to privateers and buccaneers alike. The village of Port Royal, another one that you may have heard of. And Henry Morgan, he would always circle back to Port Royal with his booty from swashbuckling and adventure.

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Katie Charlewood (28:40)

I know, I'm putting them back.

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Katie Charlewood (28:44)

Oh, scratchers. Good idea.

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Katie Charlewood (28:48)

Thanks, random singing people.

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Katie Charlewood (29:00)

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Katie Charlewood (29:10)

So Henry Morgan, the wee Welshman, he's unemployed in Jamaica. What with Venables being imprisoned and all, and in a crazy random happenstance, an opportunity befalls him. There are two pirate ships ready to set sail, and they always need decent crew members. It's quite likely that these ships were comprised of many of Venable's ex troops because, you know, they had seafaring skills and were no longer in receipt of a working wage.

Katie Charlewood (29:44)

Disclaimer. Wee disclaimer for you. Some historians will argue that Morgan was always a privateer and not a pirate. But listen, you can absolutely be a pirate and a privateer at the same time. And let me tell you, that man was definitely up to some piratey shit, okay? So yeah, he's sailing with these pirates and they did very well for themselves with their voyages, resulting in decent profits. Better than most private jails kicking about actually. And because they're doing so well, Morgan, he has a wee chin wai with some of his shipmates and suggests that they come together and use that, you know, big hunk of decent profits to buy a ship themselves.

Katie Charlewood (30:34)

And they think this is a great idea, they buy a ship. So yeah, him, his shipmates, they have a ship now. And this is the thing about pirate ships, right? What's interesting is like pirates are their own little society, right? And typically weirdly progressive, like little floating democracies. You know, they voted on how they were going to do things, on how they were going to share profits, on how they were going to run the ship. Now obviously you have to have like a big boss in charge who knows what the fck they're doing because you need, you need some, you need a captain, okay, you need that person. Just like you need someone who can steer, just like you need someone who knows how to cook. Like you need these things on your ship. So they vote and they unanimously choose Henry to be the captain. Captain Morgan. And this is a good crew. Like they are well good at this. They've got this plundering malarkey down pat and for the next few years they are marauding, raiding and getting some really great hauls. None of this shien ultimu bullshit by the way, really good stuff. And independent work as we know is all good. But sometimes a wee bit of sponsorship doesn't go awry. A bit of freelancing here and there. And so like somewhere between the late 1650s and early 1660s, Captain Morgan joins a fleet. So Sir Christopher Mings, he was putting together a fleet of ships to launch attacks against Spanish territories. Just like Venables had, what, years before, a couple years before namingz, he is outsourcing here and he amasses the largest buccaneer fleet at the time, right? So for this plan he has this absolutely massive fleet. Like for this era he's got 14 ships involved with at least 1400 pirates altogether. And this is all approved by the British crown. A huge group of privateers were provided a letter of marque. And this is just like a seafaring hall pass for murder, mayhem, looting and pillaging. In 1662, Captain Morgan led a ship and then attack on Cuba. Basically it's the second largest city on the island, right after Havana, which was the most important and the largest. Santiago de Cuba was an important port city. And unsurprisingly, this had an incredibly strong fortress at the harbor, the Castillo del Morro. Now what is surprising is that the privateer fleet took it quite easily. And they did this by destroying the shit out of it. Yeah, like, it's easy to take over when it's fcking rubble. Okay. Like, you're not trying to claim this as your own, you're just trying to tear it down. Because if you wanted, you know, this to be somewhere where you could live, if you really wanted this area to grow, to have, you know, industry, to have commerce, to have, you know, living spaces, if you wanted to do that in this area, you wouldn't have blown the out of it. I'm just saying that we should just consider that in general about the world. Captain Morgan continues privateering for Sir Mings the following year, While was the sack of Campeche, also known as the Mansfield assault, which would become the blueprint for coastal raids in the buccaneering era. Again, to slip into some context, this is all part of the Anglo Spanish war, this one 1654-1671. So we're like in the middle of that.

Katie Charlewood (35:10)

And the attack on San Francisco de Campeche was. Which was a heavily fortified coastal town in what is now like southern Mexico. This battle lasted two hours. The buccaneers sacked the city, claiming another 14 ships from the harbor and a booty of around 150,000 Spanish pieces of eight.

Katie Charlewood (35:38)

So because of the way this port had been absolutely pillaged, King Charles II of England had to officially forbid further raids of this ilk. Right. The way that this was done, because it absolutely.

Katie Charlewood (35:58)

It's basically ungentlemanly warfare. Like, because of the manner that it was done. Like, it is seen as shocking and like, there's a really bad reaction to it sort of socially. And so he has to like forbid it. Like, there is massive outrage because of just how catastrophic it was. Now you can sort of see the way that pirate raids happen. You can imagine it and lots of running and shouting and big bamboo. Like, it's violent, it is terrifying, it is destructive. Like, we put this little Hollywood wash on it and it's fun and silly. And I'm a big fan of a swashbuckling movie. And we should bring those back. Okay. We don't need magic. We don't need magic. You want to put magic in it, that's fine. Swashbuckle and adventures, man, that's a great time period. It's just. It's interesting. Anyway, I'm not gonna into, because I'll just rant. But.

Katie Charlewood (37:08)

Anywho, Captain Morgan is, like, privateering is fine and all, but what if I actually want to do something instead of waiting for the opportunity to be handed to him? And so he decides instead to attack different coastal cities. Trujillo Vil, Hermosa, Granada. Like, he's got his eyes set on all these places. Every single village fell, like, every single one of them. He takes them all. And he was gaining quite the reputation for being this, like, amazing leader, for having massive colonies, and he's, like, being feared and respected. And there's. There's just this sort of myth and legend kind of coming from it, because he's really, really good at pillaging and plundering, right? With very few loss of crew, he's well respected by his men. It's. He's. He's doing well in the piracy sphere. And, like, this reputation. It's also because he hasn't lost a lot of crew, especially, like, either by, like, defeat or by.

Katie Charlewood (38:32)

Desertion, I should say. Because the thing about being a captain, like, during this era, like I said, a pirate ship is like this little floating democracy, right? If they don't like the shit you're doing, if they think that you don't know what you're doing, if they don't respect you.

Katie Charlewood (38:52)

They'Re gonna mutiny, right? That's what's gonna happen. They're gonna take over. Someone else is gonna become captain. That's how this works, right? And his crew would have mutinied. They did not.

Katie Charlewood (39:07)

So he's gaining a reputation and people are just kind of like, oh, he's out there being a privateer. Good for him. And his family start making their way to the Caribbean. And this is what, 1665, 1666. And, you know, he does the thing that is classy if you're rich, trashy if you're poor. Marrying your cousin.

Katie Charlewood (39:37)

I mean.

Katie Charlewood (39:41)

Ah, he was into more than one type of booty. Listen, he didn't actually have any kids with his cousin. Like, there weren't any children from this marriage. So, yeah, I'm not sure he was really into booty. Like, there's no sort of documentation regarding that. Maybe he wasn't into sex, maybe he was just into like pillaging. Anywho, seriously though, this is actually a really smart move because his uncle, Colonel Edward Morgan, like I said, he was a seaman. So he had moved to Jamaica with his family and he was made the deputy governor of Jamaica. So he's like upper class now, right? So this ensured that Captain Morgan had friends in high places and these connections with the upper echelons of Jamaican society, which was solidified when he married his cousin, Mary Elizabeth Morgan. I mean, at least she didn't have to worry about changing her SOL name though I feel like less paperwork. That's nice. Anyway, he gets quite pally with Colonel Thomas Modiford, which is handy because the very year that Edward Morgan is named deputy governor, he dies. And Thomas Muddyford, he is his replacement. And Morriford here, he names Captain Henry Morgan Colonel of the Port Royal Militia. And it's round about this time as well that Captain Morgan purchases his first plantation in Jamaica. He would go on to own three. He has plantations, he has slaves. Like to be clear, Captain Henry Morgan was very much a man of his era, right? He had slaves, he had plantations. He really, really liked money. Okay, so all the swashbuckling adventuring aside, it would be weird if I didn't mention this because a lot of his like pirate booty, so he would take a portion of like treasures and trade and whatever and he would use that to purchase things like plantations. Like he invested his pirating money so that he could then make more money. Like that's.

Katie Charlewood (42:19)

It's weird that that's his honest income, but yeah, he purchased his first plantation.

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Katie Charlewood (43:36)

Now, Captain Morgan served in the Port Royal Militia as a captain before, but now he's advanced in rank and he's commanding it. And the deputy governor issued him a letter of marque against the Spanish. Now, remember, this letter of marque allowed him to attack Spanish vessels, fleets, etc. It did not approve any raids on land. This is important. Like, now and in the next episode.

Katie Charlewood (44:15)

Anyway, as it so happens, around about the same time as this is going on, these pirates called the Brethren of the Coast. Like, I mean, that's actually a pretty cool name. We are the Brethren of the Coast. I mean.

Katie Charlewood (44:34)

When you're a professional pirate, you'll be honest, brave, and free the soul of decency. Anyway.

Katie Charlewood (44:44)

So these Brethren of the coast, they were in need of an admiral because they lost their somehow, maybe to dysentery, maybe to something else. Whom's to say? Naturally, being a big lover of booty, he accepts the possession. And now, well, now he has an entire fleet of buccaneers under his admiralty. So now he's Admiral Morgan.

Katie Charlewood (45:13)

So.

Katie Charlewood (45:16)

His reputation certainly preceded him. And he's seen as the king of buccaneers. And he is fucking loving it, by the way. Like, he uses his privateer fleet to. Because, again, he's got his letter of mark. He uses this to attack the Spanish. And even though he's not supposed to attack land, he's gonna do it anyway, right?

Katie Charlewood (45:46)

The audacity is not new, lads. It's not new. Like, it's been around quite a while.

Katie Charlewood (45:54)

He considers attacking the very heavily fortified city of Havana, but realizes that on the scale of zero to invading Russia in the winter, this is attacking a Caribbean fortress with not enough men. Mm. And so he chooses a new target, that of Puerto Principe, which, by the way, this was. This is a total shit show. So here's the thing. They're on the ship, they're planning their attacks, they're laying out all the details, schemes, you know, the backup plan, the whole lot, all in front of a Spanish prisoner. They're doing it in front of this guy.

Katie Charlewood (46:44)

Why? What? Why would you be doing it in front of the prisoners anyway? Like, clear, you should be doing this privately. I'm not. Again, I am not teaching people how to rob effectively. I'm just saying you could be smarter.

Katie Charlewood (47:01)

So. Of course, not one person considered that maybe, just maybe, it was possible that the aforementioned prisoner could speak English.

Katie Charlewood (47:14)

Spoiler alert, he did. So when the Ship got to a bay which is like near Puerto Principe. The aforementioned English speaking Spanish prisoner escaped. He swam to shore and warned everyone of the attack.

Katie Charlewood (47:33)

So the governor gets notified and he sends messengers through the street and they are preparing for the attack. The entire town is woken up and they're telling people to go hide their valuables.

Katie Charlewood (47:48)

So when the pirates attack the town, not only are they faced with resistance that they weren't expecting, this battle lasts four hours. Now the Spanish, they are absolutely bollocks, right? They are, they are, I'm, I don't want to say annihilated, but they are pretty beaten down by this pirate crew. And eventually the pirates demand a surrender or they will burn the town to the ground.

Katie Charlewood (48:22)

You would be surprised how many, how many solutions there are to problems that involve arson.

Katie Charlewood (48:33)

So they're like, we're gonna do that, but also we are going to viciously kill all of the women and children in Puerto Principe in front of all of you.

Katie Charlewood (48:46)

If you don't surrender.

Katie Charlewood (48:51)

So the Spanish surrendered. They had suffered heavy losses and then the buccaneers had like barely any loot. Like there wasn't a lot of return for the amount of effort that had been put in here. So they decided to lock the Spanish in their churches.

Katie Charlewood (49:21)

And then they decided they were going to try and like search the town. So they plundered. They were trying to find valuables and whatnot, but most of them had already been removed from the town and hidden away. So yeah, there was very little reward for this outright act of illegal piracy.

Katie Charlewood (49:42)

Unsurprisingly, Captain Morgan is pissed. So he decides that he's going to starve the prisoners locked in the churches and then the pirates torture them.

Katie Charlewood (49:56)

This may shock you, but pirates were not exactly the most patient of people. And so they're like, this is bullshit. And they give the Spaniards an ultimatum.

Katie Charlewood (50:12)

Provide two ransoms or suffer. Right, that's it, that's, that's the ultimatum. If they paid these ransoms, they'd be fine. So like there the two ransoms are, there's one for the town and one for their lives. So if they, you know, paid the ransom for their life.

Katie Charlewood (50:35)

Then the town would be burnt to ash before their eyes.

Katie Charlewood (50:42)

If they didn't pay any ransom, the town would be set ablaze and the prisoners would either be killed or taken to Jamaica and sold off as slaves. Yeah, these guys were not fucking about. So four prisoners, they offer to go find the hidden goods and valuables and they're like, there's some people who've Run away with some of the goods as well. Like they've gone. We'll find them, you know, and we'll bring them back. And these guys are warned, they're like, listen, if you don't return, there's gonna be so much death, like the streets will be red with blood and we will kill every member of your family. We're gonna destroy everything and you will come back to blood and ash. And so they're out there for a couple days and they come back empty handed, right? They're like, we couldn't find it, but. But they play with Captain Morgan to give them 15 days, which is an oddly specific number. And they're like, we will pay you the whole shebang. Fifteen days. And he's like, you know what? Yeah, why not sure.

Katie Charlewood (52:00)

He's like, I'm here now. Like I may as well like wait. And so these prisoners, they go away and they come back within the agreed time frame and they bring with them a sweet, sweet chunk of booty and even more prisoners, right? They're like, we found these guys hiding and we brought this. And we brought this. Hooray. And so the pirates, obviously, they search, you know, all the prisoners just in case they've got anything else hidden on them, like maybe some valuables, maybe something else. And they do.

Katie Charlewood (52:42)

So as they're searching, they find a letter from the Governor of Santiago who tells them to drag it out, you know, as long as they can, so that they can send reinforcements to fight the pirates. So Henry Morgan, he is reading this letter and he is not a happy bunny, right? He is angry. And so he orders all of the treasure to be put on the ships. And then he tells the prisoners that they have one day to pay their ransoms, right? Like you got one day or else. And the Spanish are, they're begging for more time. But he is so done at this point that he's just like.

Katie Charlewood (53:29)

No, I can't give you any more time. I'm absolutely done with this whole thing. And like, to the point, like he's so fcked off with this whole scenario that he just takes 500 cows with him. Like.

Katie Charlewood (53:46)

I sht you not. They're like, we don't have money. I got these cows though, okay? 500 cows. And he's like, I, I guess I could eat, you know? And so his crew are there and they're cutting up the cows, right? Because they're just like divvying stuff up and they're figuring out what they're gonna do.

Katie Charlewood (54:06)

So while this is happening, two Crew members get into a fight, one French, one English, right? And they challenge each other to a duel, which is supposed to be a fair fight. But when they get to the meeting point to do the duel, right, the English fella stabs the French guy literally in the back, right? And another Frenchman, he wants revenge, and it's a whole thing. Captain Morgan does not allow insurrection amongst his ranks. A fair fight is fair. A challenge with honour is fine. But this stabbing in the back, bullshit, absolutely not. So the Englishman, he's viewed as treacherous, right? This is, this is dodgy behavior. And so he's putting chains and he was to be hanged in Jamaica. Like, that's the goal. Being brought back to Jamaica. He's going to get hanged.

Katie Charlewood (55:08)

Because, you know, Sweden. And as far as raids go, this was piss poor 50,000 pieces of 8 and 500 cows, which, not really that much when you have to consider it has to be shared between 700 or so men.

Katie Charlewood (55:29)

Now, Morgan, obviously, he thinks it would be best to attack another town, you know, to try and reap some more rewards, you know, make up for the loss. But the French ships that were part of this fleet, they. They weren't keen on this idea and they went their separate ways. But it was like a totally cool separation, like, no harm, no foul. They were like, we, we're kind of done now, no worries. And so Captain Morgan takes, you know, the remaining fleet and they return to Port Royal, where he had the English crew member hanged because, you know, he was severe, but he was true to his world, right? So he's lost a good chunk of his fleet thanks to the whole backstabbing incident. But of course he wants more booty, because of course he does. And, like, he's lost, what, 30% of his crew, but he's still like, let's go bigger and big better. Like he's chasing that next. That next sort of raid. Like an adrenaline junkie, but, like, for pirating.

Katie Charlewood (56:42)

So it's what, 1668 at this point, and the fleet set sail to where? Well, Captain Morgan had learned his lesson about talking about his plans in front of people.

Katie Charlewood (56:57)

So his fleet, they're following his lead and they get close to Costa Rica, and he tells his captains his plan to pillage the town of Portobello under the COVID of darkness. And he tells them that he wants to steal every damn valuable from this frankly, massive city.

Katie Charlewood (57:22)

Is this pride? Is this ego? Is this just.

Katie Charlewood (57:29)

Like, like the whole thing of gambling, like you're just chasing that next rush? Is it like a dopamine thing? For him. Now, his captains, they question this very audacious plan because to put it simply, they do not have enough men. But Henry Morgan, he's just like, less men means less people to share treasure with. Like, he is so self assured. Like he genuinely doesn't believe that they can fail. And here's, here's the thing. Portobello is not a place you want to fck with. Like, apart from Havana and Cartagena, like, no, no, like, like it was the strongest place owned by Spain in the West Indies, right? This would be a challenge for any fleet, let alone one much reduced.

Katie Charlewood (58:27)

Not only was the very entrance to the city guarded by two castles, there were many more inside the city for people to shelter in if there was an attack. So you've got 400 families there or thereabouts residing in this ridiculously well fortified city, along with a garrison of about 300 soldiers, right? He's only got about 460 men, right? Those numbers are not good. This is not an easy peloton plunder scenario. But Captain Morgan clearly has something to prove.

Katie Charlewood (59:06)

And so they decide to be sneaky deaky about it and they carefully head up river. They transfer from the ships into smaller boats and even like canoes. There's like 23 of them. All in all, because they don't want to be noticed, they make it to land, they reach the guard post, the first one. It is manned by a single guard who they very quickly overpower, question and bring with them. It's by the time they get to that sort of first point, it's sort of early hours of the morning, like it's still nighttime, but it's that kind of time. So he's telling them all about the city and how to maneuver it, like. And so when they get to the castles at the entrance of the city, they line up against the castle walls, you know as not to be seen.

Katie Charlewood (60:05)

And then the guard they've captured, right, Morgan orders him to call into the castle and tell the soldiers within to surrender or they'll be cut into pieces with no mercy. And so he shouts in and says the thing. And.

Katie Charlewood (60:23)

Instead of surrendering Morgan, the Spanish garrison just starts shooting at the pirates. And this fight starts, but it is over fairly quickly because inside the castles there were explosives, right?

Katie Charlewood (60:41)

It's like this clay pot which we set alight and thrown kind of like an old timey grenade, right? So what they would do is they would infiltrate the castle and, and take it from inside.

Katie Charlewood (60:55)

So then when the pirates were in, you know, they did what they threatened to do, which was slice up the Spanish. Now, they didn't dice everyone because they didn't have time for that. Instead, the remaining soldiers were locked in a small room.

Katie Charlewood (61:14)

In this castle that is full of old timey grenades and gunpowder.

Katie Charlewood (61:22)

So on the way out, they set it alight and it goes boom.

Katie Charlewood (61:31)

This not the most subtle of moves and does not go unnoticed by the people in the city. The citizens are just like chucking valuables into wells. They'll hide in shit because, you know, massive explosion has happened and they don't want to lose everything they have. And the governor could not do sht, right? He's trying to rally troops, he's trying to rally people. He cannot do either. And so like Princess Peach, he runs off to another castle. And the pirates are absolutely, well, pillaging the out of Puerto Bello, right? They're on hour 12. So like they are 12 hours of plundering. How are they not tired exactly? Like, there's a lot to say for adrenaline. And so even though they had looted a lot of stuff, they knew that there were higher classes. And the governor, they were all hiding in these other castles in the city.

Katie Charlewood (62:37)

Naturally, they assumed a whole lot of that treasure would be in there with them. So Captain Morgan takes a small force to attack the governor's castle and a few other teams, like they split up, right, and they go attack. Now the governor's castle is so well guarded that they beat back Morgan and his men. Meanwhile, Captain Morgan saw that the other castles were being taken by his crew because they were raising their throne.

Katie Charlewood (63:06)

And I think his ego got the best of him here because he's just infused with. I don't know if rage is the right word, but definitely a terrible, horrible, horrible idea. He gets one of his men to round up as many religious men and women as he could find.

Katie Charlewood (63:28)

Super Catholic Spain, remember, very religious. So he's got nuns, priests, monks, anybody he can get his hands on, right? He gets the crew to make 12 ladders that were wide enough that they could hold three or four people at a time. So they could climb three or four at a time.

Katie Charlewood (63:47)

So these ladders were placed up against the castle walls. And he makes these, you know, religious men and women climb up.

Katie Charlewood (63:58)

Gently, followed by his pirate crew. So.

Katie Charlewood (64:04)

He makes the assumption that the governor of super Catholic Spain.

Katie Charlewood (64:11)

I mean, one that he wouldn't fire on his own people, and he especially would not fire on people who had taken religious orders, right? He couldn't shoot men and women of God. Like, like that's, that's just A no brainer, right?

Katie Charlewood (64:29)

He assumed incorrectly. So all of the nuns, priests, whatever, climbing up the ladder, they were fired upon and they are begging and pleading, but to no avail, right? They're begging the governor to just stop firing, but he is just killing everyone.

Katie Charlewood (64:51)

The pirates climb up after all of these, like, religious people, like they're using them as human shields effectively. So they get up and they overpower the castle.

Katie Charlewood (65:04)

All of the Spanish soldiers surrendered, right straight away. No, no issue. The governor was so pissed the, that he shoots at them and he kills some of his own soldiers. The pirates offer him the chance to surrender and he tells them he'd rather die. And so they kill him.

Katie Charlewood (65:31)

So, yeah, the city is now under the power of the pirates and they're just living it up. Like they've been doing this for what, a whole day nearly. They're tired, they're, you know, they relax and be cool, everything's fine, have a party. They spend the next fortnight in Portobello, drinking, feasting and just having a damn good time. They've earned this.

Katie Charlewood (65:57)

And Captain Morgan, who loved a good ransom, demands 100,000 pieces of eight from the city.

Katie Charlewood (66:05)

And so they send two men over to the city of Panama, like pre Canal fame, by the way. And they're like, go get your money. So these guys, they tell the President of Panama about the attack. And so he gathers a force, right, to deal with the pirates. But first he sends a letter to Captain Morgan warning him that if the pirates do not get the heck at a dodge, they will receive no mercy.

Katie Charlewood (66:39)

But Captain Morgan, a man with balls so big that you'd think he had elephantitis of the scrotum, he responds with the threat that if he doesn't get his money, he's going to burn Portobello to the fucking ground.

Katie Charlewood (66:58)

And he'll go once he has his damn money.

Katie Charlewood (67:02)

So the President of Panama just pays it. Not only does he pay the ransom, but he, like, he's writing his letters and he's like, hey.

Katie Charlewood (67:13)

How did you take the city with so few men? And Captain Morgan responds by sending him a pistol with a note telling him to watch over it and you'll soon come to Panama to collect it.

Katie Charlewood (67:30)

The President sends the pistol back because this is the least fun pen pal he has, and warns him that Panama would not be as favourable to him as Porto Bello had been. The President also had massive balls because Captain Morgan was not a man to be trifled with.

Katie Charlewood (67:51)

But they have verbat. And so they return to Jamaica. Now these fellas like Their money is shared. They get their pay. Whatever he's investing in his plantations.

Katie Charlewood (68:03)

So these pirates, right, these privateers, they spend every single one of the 250,000 pieces of eight. Okay. Like, it doesn't take them long. It's like two weeks, three weeks maybe it's a few weeks. And these big spenders are on the lookout for their next adventure.

Katie Charlewood (68:29)

But that's gonna be for next time.

Katie Charlewood (68:37)

Yeah, I'm stopping it here because we have more to talk about. So I'm gonna make that into another episode, which you're going to get very soon if you don't already have it. So that is the story of half the story of Captain Morgan. Because it's. It's gonna get worse. It's gonna get worse now.

Katie Charlewood (68:57)

Oh, I. Oh, goodness, I didn't tell y'. All. I. I'm in Belfast in the first of February. It's for Imbolk. It's like St Bridget's Day. It's. Oh, my God. I'm probably gonna talk about some cool women. That's a live show that's gonna be in Belfast. And the sunflowers on the socials. Come see me. If you're thinking, oh, I don't know what to get someone for Christmas a ticket to see me, I'm amazing. More gigs will be coming out over the year. More stuff's happening. I've got big news to share. It's going to be coming. It's going to be fabulous now. Yeah. Anything else? Anything else to share with you at the end of the show?

Katie Charlewood (69:39)

Yeah. I'm so excited to have, like a month of pirates because it's just a really fun era. It's a really fun era to talk about. Although what I've noticed is some people have such an issue with the term the golden age of piracy. I'm like it. That's just what it's called. It's like how we call things the Victorian period or the Gilded Age or whatever. It's just a name we give things. It's fine. Don't freak out about it. But. Yeah, that's what that is. But I guess we are on to recommendation. Time for listening. I'm gonna put the link in the description down below. Danny Vadilla, he's got a song called Stay Mad. Look at me promoting men today.

Katie Charlewood (70:24)

So, yeah, there we go. You can listen to him. It's really catchy. Come on, let's do. Do a thing. Also, I've got such a thing. I'm going to pause sidebar for recommendations.

Katie Charlewood (70:38)

I'm the person who believes that we should be like, always, like, interact with your friends content, share it, boost it. Like, don't just like and scroll because you want to show the algorithm that you're interested in the content. Like, you really need to engage with it. You know what I mean? You need to interact with the content. And I think that's really important when it comes to our friends, like, because I know a lot of, a lot of the platforms are being a bit dickish right now, and so we need to share their stuff. Like that's, that's something we need to do. And I think it's very important to share your friends stuff. Like you can't buy stuff all the time or do whatever, but if you share it and comment on it and do stuff, interact like, it helps, boost it, right? It's just a good thing to do. Now I do owe Dani a bagel, which is not why I'm sharing it. I do actually think it's a really catchy song. So listen to Dani's song, stay mad. Okay, let's do this. Now, for watching, for reading, I'm gonna go with the Murder Game by Tom Hendle. Look at me supporting more men. And for watching, for watching, watching, watching. What should I recommend? I feel like I'm on a role with like, men. You know what? Daniel Sloss, Daniel Sloss's new comedy special, can't. It's on danielsloss.com Go check that out. There you go. I've supported three men this episode. Who knew I could do it? Listen, I don't hate men, okay? Some of my best friends are men. But those are your recommendations for today. So adios. Au revoir, au vuitize, my friends. Bye. Bye.

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Katie Charlewood (73:36)

I know. I'm putting them back.

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Katie Charlewood (73:40)

Oh, scratchers. Good idea.

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Katie Charlewood (73:44)

Thanks, random singing people.

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Katie Charlewood (73:56)

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