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Drake's 1585-86 expedition to the Spanish Indies strategically undermined Philip II's financial credit, even though it wasn't as lucrative as hoped.

Though Drake failed to capture treasure ships, his sacking of Spanish colonial cities exposed vulnerabilities in Spain's empire and caused European bankers to refuse loans to Philip II. ✦ AI generated

Tom Holland · The Rest Is History · 2026-08-10 · original ↗

starts at this moment · 48:02

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And so Sydney must um be terribly excited about this.

And this isn't a long expedition. He's back in Plymouth by the 22nd of July 1586. And actually, and it's not quite as lucrative as Drake had been hoping. He doesn't manage to capture any treasure ships, but strategically it is hugely significant because as he done before, he's able to highlight the pretty precarious nature of Spain's American empire. And the result of this in Europe is to undermine Philillip's credit with his bankers. And so the Pope and the Dukes of Florence and Seavoi all refuse him a loan when the news of Drake's expedition reaches them.

verbatim transcript · starts at 48:02

Transcript · around this moment

47:55Colombia, which he also captures again. He extorts a massive ransom. And this isn't a long expedition. He's back in Plymouth by the 22nd of July 1586. And actually, and it's not quite as lucrative as Drake had been hoping. He doesn't manage to capture any treasure ships, but strategically it is hugely significant because as he done before, he's able to highlight the pretty precarious nature of Spain's American

48:22empire. And the result of this in Europe is to undermine Philillip's credit with his bankers. And so the Pope and the Dukes of Florence and Seavoi all refuse him a loan when the news of Drake's expedition reaches them. And the bank of Seville actually goes bust and Burley is kind of cackling and rubbing his hands at this and says truly Sir Francis Drake is a fearful man to the king of Spain

48:47which I think he is. So while Drake's been off sacking Cartahena and whatnot, what has Sir Phillip Sydney doing? Because he's been in the slightly more unglamorous uh surroundings of flushing on the uh what's that coast of modernday um >> Yeah, it's an island. Is that Yeah. an island off off uh off the shelter. Yeah. So he's arrived there in mid- November which is never really a great time to

49:12turn up to an island in the North Sea. Um it's completely miserable and when he lands he has to walk three miles through mud before he can reach the port itself. And he wrote to Lester as dirty a walk as ever poor governor entered his charge with all. Lester himself arrives in Flushing three weeks later and he's greeted there by Sydney um by the two sons of William the Silent and by

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