Who Did What Now – Episode 170
Captain Morgan: Privateer, Pirate & Buccaneer – Part I
Host: Katie Charlwood | Date: December 10, 2025
Main Theme & Purpose
In this lively and irreverent episode, host Katie Charlwood kicks off "Pirate Month" by delving into the origins and early career of the legendary Captain Henry Morgan. Charlwood brings her signature wit and unfiltered perspective to the story, examining Morgan’s rise from rural Welsh roots to notorious privateer, pirate, and buccaneer in the Caribbean. The episode unpacks the historical contexts of piracy, privateering, and colonial conflict, while exploring the murky legality and brutal realities that defined the so-called "Golden Age of Piracy." This is the first half of Morgan’s story, promising an even wilder continuation in part two.
Key Discussion Points & Insights
1. Why Pirates? Why December? [03:40]
- Katie shares her reasoning for a pirate-themed month:
- December can be tough—especially for the neurodivergent and those affected by holiday stress. Pirates offer a “fun” historical distraction.
- Acknowledges the ugly side of piracy: “I am going to be talking about raiders, marauders, pillagers, plundering, murdering, torture. Robbing, stealing, slavery, colonialism and just a whole lot of crime.” [05:01]
2. Sourcing & Research [05:32]
- Katie lists a robust, diverse array of sources, ranging from classic histories to modern scholarship, establishing the episode’s research rigor and occasionally poking fun at her own pronunciation gaffes. [05:32–07:48]
3. The Welsh Origins of Henry Morgan [08:15]
- Born around 1635 in Wales—possibly Pencarn or Llanrumney—Morgan’s background was rural, not noble.
- Katie breezily clarifies UK geography and Welsh/English distinctions.
4. The Mystery of Morgan’s Journey to the Caribbean [10:45]
- Two main theories:
- Part of Robert Venable’s army dispatched to the Caribbean under Oliver Cromwell.
- Traveled as ship crew and became an indentured servant in Barbados.
- Katie contextualizes indentured servitude vs. slavery, emphasizing their profound differences. [12:08]
5. The Golden Age of Piracy, Its Periods & Definitions [12:29]
- Golden age: c. 1650–1730, divided into:
- Buccaneering period (1650–1680)
- Pirate Round
- Post–Spanish Succession period
- Key terms defined:
- Buccaneers: origin traced to “boucan,” French for a smoking grill, becoming local game hunters-turned-pirates.
- Privateers: pirates with royal approval (“letters of marque”), essentially outsourced warships for states.
- Corsairs: Mediterranean pirates, some state-sanctioned, who created “massive geopolitical headache[s].” [17:41]
“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.” [17:41]
6. The Anglo-Spanish Wars & British Imperial Blunders [20:25]
- Venables’ failed invasion of Hispaniola in the 1650s compared to “invading Russia in the winter” in terms of disastrous planning [21:31].
- Subsequent British capture of Jamaica (with Henry Morgan among the invading force), the accidental foundation of Port Royal, and the grim effects of disease on the British occupation. [25:09]
7. Morgan’s Transition from Soldier to Pirate/Privateer [29:10]
- Post-invasion, with British officers imprisoned or dead, Morgan (and many ex-soldiers) were jobless in Jamaica. Pirate crews provided employment and camaraderie.
- Formation of pirate “micro-democracies” aboard ships:
“Pirates are their own little society, right? And typically weirdly progressive, like little floating democracies.” [30:34]
- Morgan is elected captain by his peers—thus becoming Captain Morgan.
8. The Rise of Morgan’s Reputation & Pirate Operations [34:46]
- Joins Sir Christopher Mings’ massive fleet (~14 ships, 1400 pirates) on British-crown-sanctioned raids.
- Describes easy destruction-and-loot tactics during Santiago de Cuba and Campeche raids, resulting in huge hauls and ultimately official censure from Charles II for “ungentlemanly warfare.” [35:10–37:08]
9. The Cruelty and Pragmatism of Bucaneer Warfare [47:48]
- Detailed account of the Puerto Principe fiasco:
- Pirates plan attack in front of a Spanish prisoner—who escapes, warns the town, leading to hard-fought resistance, little loot, and tortured ransoms.
- Shows pirates’ cruelty, including threats to massacre civilians and use of starvation and torture to exact ransoms.
- Result: measly loot and 500 cows [53:46] for hundreds of pirates—a poor payout that leads to unrest and strict discipline (including an execution for dishonorable dueling).
10. The Legendary Raid on Portobello [56:57]
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Despite reduced numbers, Morgan leads a bold, “audacious” [57:22] raid on the heavily fortified Portobello.
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Innovative assault tactics, human shields (religious captives), psychological warfare, and extreme violence.
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Massive ransom extracted by threatening to raze the city; Morgan’s brashness in negotiating sends panic to Panama’s president, including a pistol with a taunting message:
“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.” [67:13–67:30]
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Pirates indulge in an extravagant celebration with their haul, spending it all within weeks—never satiated, always seeking the next rush.
11. Henry Morgan’s Social Mobility and Plantations [41:25]
- Morgan cements his place among colonial elites:
- Marries his cousin, ensuring “connections with the upper echelons of Jamaican society.”
- Purchases plantations (using pirate loot) and owns slaves—Katie underscores this grim, historically accurate detail:
“Captain Henry Morgan was very much a man of his era... He really, really liked money.” [41:25–42:19]
12. The Pirate Social Structure: Discipline and Mutiny
- The democratic and meritocratic aspects of pirate life repeatedly emphasized: captains served only by consent of their crew and could be deposed at any time. Morgan’s firm but fair discipline keeps him in command.
Notable Quotes & Memorable Moments
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Katie on Morgan’s character:
“The audacity is not new, lads. It’s not new. Like, it’s been around quite a while.” [45:46]
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On Portobello’s defense:
“Here’s the thing. Portobello is not a place you want to f*ck with. Like, apart from Havana and Cartagena... it was the strongest place owned by Spain in the West Indies. This would be a challenge for any fleet, let alone one much reduced.” [57:22–58:27]
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Morgan’s balls/ego:
“Captain Morgan, a man with balls so big that you’d think he had elephantitis of the scrotum...” [66:39]
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On pirate equality/democracy:
“A pirate ship is like this little floating democracy, right? If they don’t like the shit you’re doing, if they think you don’t know what you’re doing, if they don’t respect you—they’re gonna mutiny, right?” [38:32]
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Katie summarizing the economics of piracy:
“It’s weird that that’s his honest income, but yeah, he purchased his first plantation.” [42:19]
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On Hollywood depictions:
“We put this little Hollywood wash on it and it’s fun and silly. And I’m a big fan of a swashbuckling movie…but, like, it’s violent, it is terrifying, it is destructive.” [36:38]
Important Timestamps
- [03:40] – Why pirates, why December: history, emotions, and neurodiversity
- [05:32–07:48] – Sources and humor about historical research
- [08:15] – Morgan’s Welsh boyhood and ambitions
- [10:45–12:29] – Theories on how Morgan reached the Caribbean; importance of indentured servitude
- [12:29–17:41] – Golden Age of Piracy explained: key terminology, context, and legal vs. illegal piracy
- [21:31–27:13] – Venables’ failed invasion(s), Jamaica's accidental conquest, and disease
- [29:10–30:34] – Emergence of pirate democracy; Morgan’s ascension
- [34:46–37:08] – Morgan’s fleet actions, notably Cuba and Campeche
- [47:48–55:29] – Puerto Principe disaster, pirate cruelty, ransoms, and lack of profit
- [56:57–68:29] – Daring and devastating sack of Portobello; legendary psychological warfare and enormous ransom
Episode’s Tone
- Katie is witty, sardonic, and unflinching—balancing historical accuracy, humor, and social commentary.
- She doesn’t shy from the brutality and moral ambiguity of pirate life or gloss over the real horrors of colonial slaveholding.
- The episode is as much about busting myths and cinematic stereotypes as it is about relishing real-life adventure.
Concluding Notes
- The episode concludes with Katie promising a Part II—“Because it’s going to get worse”—teasing further dark adventures ahead.
- [68:29] “But that’s gonna be for next time.”
- Katie’s recommendations (music, books, comedy), and a recurring call for listeners to engage with their friends’ creative work (support, share, interact), rounding off the episode in her typically inclusive, communal tone.
For Next Episode
- Expect an escalation in both violence and audacity as Morgan continues his pirate/privateer career.
- Katie hints at more historical insight and no shortage of wild, swashbuckling stories to come.
Summary prepared to flow as a stand-alone guide for listeners and non-listeners alike.