Who Did What Now: Episode 171 – Captain Morgan: Pirate, Knight & Politician – Part II

Host: Katie Charlwood
Date: December 13, 2025

Episode Overview

In the riveting second half of the Captain Henry Morgan saga, Katie Charlwood dives deep into Morgan’s transformation from notorious pirate to celebrated knight and cunning politician. With her hallmark wit and relentless fact-checking, Katie unpacks the myth and reality behind the infamous Welsh adventurer. She exposes the brutal details of his Caribbean campaigns, his fraught relationship with colonial governance, his eventual legitimation by the British Crown, and the bizarre twists that followed his death. This episode does not shy away from confronting both the violence and the legacy-building that made Captain Morgan a legend—while challenging the romanticized image of pirates in popular culture.

Episode Structure & Key Segments

1. Catch-Up and Setting the Scene ([02:11]–[05:00])

• Katie recaps Part I: Morgan’s origins, rise to captaincy, marriage, and reputation for ruthless privateering, as well as the blurry legality of his actions under British law.
• Notable quote:

  “Henry Morgan, actually, Harry Morgan, was Welsh. He moved to Bristol, ended up in the West Indies … joins a pirate crew, becomes a captain, gaining a no-fucking-around reputation, becomes a privateer, marries his cousin, becomes an admiral and commits blatant acts of illegal piracy.” (04:25)

2. Piracy, Propaganda, and Legal Gray Areas ([05:00]–[11:00])

• Morgan’s attack on Portobello exceeded his letter of marque—making it outright piracy, not legal privateering.
• Katie addresses pushback from listeners (especially “men in my comment section”) who try to dispute Morgan’s criminality.
• She details the professional divides among historians:

  “The level of confidence one has to have to argue with a historian over a topic that they have quite aggressively researched, fact checked. … The audacity.” (07:12)

• Thomas Modiford’s political maneuvering as Morgan’s superior and governor: trying to dissociate himself from illegal acts while spinning narratives about Spanish threats to justify attacks.

3. The Cartagena Mission and the Catastrophic Explosion ([17:20]–[27:11])

• Morgan’s plan: attack rich Spanish holdings, especially Cartagena.
• Detailed sequence: On Cow Island (Île-à-Vache), Morgan absorbs a Royal Navy frigate into his fleet.
• Showcases Morgan’s cunning in dealing with French pirates—inviting them aboard, then capturing their ship due to a technicality over unpaid provisions.
• Disaster strikes:

  “The Oxford exploded because, again, all of the gunpowder, the ship was destroyed and 300 of Morgan’s men were dead. … Karma is a bitch, like me.” (25:01)

• Morgan salvages valuables from corpses, recovers, and re-assesses his strategy.

4. The Maracaibo and Gibraltar Raids – Torture & Terror ([28:17]–[43:11])

• After losing key ships and hundreds of men, Morgan sets eyes on easier targets: the towns of Maracaibo and Gibraltar (modern Venezuela).
• Katie ensures listeners don’t miss the brutality:

  “They find 30 people. They bring them back and immediately start torturing them. This torture lasted for three whole weeks. Three weeks of the rack, of beatings, of burnings…” (32:37)

• The pirates torture a mentally disabled man in Gibraltar for a pittance and vent even more rage upon him, highlighting the dark reality behind the swashbuckling stories.

5. Escaping the Spanish Trap – Cunning and Deception ([43:41]–[52:00])

• Facing a blockade by the Spanish navy, Morgan’s democracy aboard ship is highlighted as he consults the crew.
• Intricate ruse: pirates deploy a fire ship, disguised with men-shaped logs; it destroys Spanish vessels, leading to their escape:

  “They plan to send out a fire ship … they make it look fully manned, so they have logs that are dressed in men’s clothing … The ship, on fire, collides with the Spanish ships ... causing it to sink.” (45:27)

• Further deception: repeated feints at landing with rowboats trick the Spanish into undermanning the sea-facing cannons, letting the pirates sail away.

6. The Panama Campaign – Outlaw to Hero ([52:00]–[60:00])

• After increasing Spanish-British hostilities (including Spain declaring privateering against the English), Morgan is authorized by Modiford to wage war.
• Morgan leads a massive campaign: taking Providence Island, storming Chagres Castle (losing 150 men), and enduring a grueling cross-country march to Panama City.
• The Spanish preemptively torch Panama City. The booty is scant; most of Morgan’s men perish on the return journey.
• Nevertheless, Morgan is greeted as a hero in Jamaica—reinforcing his complicated legacy of outlawry and patriotism.

7. Political Reckoning – From Pirate to Knight ([60:00]–[65:00])

• In a twist, Morgan’s acts spark diplomatic crisis: his superior Modiford is sent to the Tower of London, and Morgan is summoned to England.
• Morgan defends his actions before King Charles II with aplomb:

  “This level of just, again, massive cojones, right? Just huge. Just ... the testosterone oozing out of this man … King Charles was like, really into it.” (63:19)

• Instead of punishment, Morgan is knighted and later returns to Jamaica as Lieutenant Governor and political power-broker.

8. Morgan’s Later Life and Death ([65:00]–[72:00])

• As a politician, Morgan turns a blind eye to continued piracy and presides over Port Royal’s evolution as a pirate haven.
• He enforces martial law and is eventually stripped of some titles after political rivals accuse him of corruption.
• In declining health, Morgan dies of dropsy (oedema) in 1688.
• Notable eulogy:

  “On 25 August 1688, Henry Morgan died in his sleep … Amnesty was declared so that privateers and pirates could pay their respects without being arrested.” (69:18)

• His wealth at death: equivalent to over £1.1 million today. His estate passed not to direct descendants, but to relatives and godsons required to adopt the Morgan name.
• Four years after his burial, an earthquake sinks Port Royal—and Morgan’s grave—into the sea.

9. Reflections, Facts, and Cultural Notes ([72:00]–[76:00])

• Katie addresses the “Henry vs. Harry” Morgan name debate, clarifying pronunciation and historical usage.
• Fun fact: The famous Captain Morgan rum is truly a rum (not bourbon), despite confusion owing to barrel-aging methods.
• Closing recommendations:
  • Watch: “Muppet Treasure Island”
  • Listen: "Stay Mad" (independent artist)
  • Read: Robert Louis Stevenson’s "Treasure Island"
• “So ends the story of Captain Morgan. Actually, now I’m going to look up this rum thing one sec … apparently, flavoured rum because it’s a blend of rums with Madagascar and vanilla. … No man is an island unless his name is Madagascar.” (74:45)

Notable Quotes & Memorable Moments

• On historical debates:

  "The audacity. Like, you're not an expert on piracy, just ’cause you used to burn DVDs, man. ... You really need to stop." (08:55)

• On Morgan’s lack of mercy:

  “He collects them all together, they search them for valuables, and then they dump them back into the ocean to, to be devoured by the monsters of the sea. The monsters of the sea. That, that was my attempt at Welsh.” (26:14)

• On pirates and democracy:

  “Which is very democratic. Like I said, pirate ships … floating democracies, right?” (44:24)

• On the disaster at Panama:

  “When they land outside Panama City, they are met with a Spanish force of 2,500 men, … and these Spaniards, they fire a single shot and then they bolt it. … What’s weirder is that when they get into the city, almost every building is burning.” (57:37)

• On burial and Port Royal’s fate:

  “An earthquake strikes Port Royal and like two thirds of the town sank into Kingston Harbour, right, including Palisades Cemetery. So Captain Morgan’s grave … goes into the sea and it’s never recovered because of course it isn’t, because earthquake and the sea and monsters of the ocean.” (71:40)

• On legacy and historical myth:

  “So ends the story of the pirate and privateer, because you can be both at once. Henry Morgan.” (72:09)

Tone & Style

Katie blends sharp historical analysis and irreverent humor (“boom shakalaka boom … I’m too white to say that”) to keep complex tales accessible and engaging. She is unafraid to call out romanticized or misleading portrayals of pirates, stresses the atrocities they committed, and frames Morgan’s legacy within the realities of colonial politics and violence. Her asides lend personal flavor and invite listeners to question their own assumptions, especially about how history is remembered and retold.

Timestamps for Key Segments

• [02:11] – Introductions, personal anecdotes, and recap of Part I
• [05:00] – Modiford, Morgan’s letter of marque, and politics of piracy
• [17:20] – Formation of fleet, Cow Island rendezvous, naval buildup
• [25:01] – The explosion of the Oxford and mass casualties
• [32:37] – The torture and plundering of Maracaibo and Gibraltar
• [43:41] – Escaping the Spanish blockade with a fire ship
• [52:00] – The Panama campaign and aftermath
• [63:19] – Morgan’s knighthood and royal approval
• [69:18] – Morgan’s death, funeral, and posthumous legend
• [74:45] – Captain Morgan rum fact-check and cultural recommendations

Summary

This thorough, darkly humorous episode departs from romantic pirate lore, instead showing the calculating, violent, and daring life of Captain Henry Morgan. Listeners come away with a clear understanding of Caribbean colonial politics, the line between privateers and pirates, and the construction—and deconstruction—of historical myths. Katie’s vibrant delivery, sharp critiques, and honest reflection make Part II an unmissable tour de force of historical storytelling.