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After being humiliated in the Spanish ambush at San Juan de Ulúa in 1568 — where the Spanish killed and captured dozens of the English slavers — Drake declared war on Spain personally, abandoning trade as a mug's game and concluding that piracy was the real money since Spain's defenses in the Indies were dangerously weak.

The speaker recounts the devastating 1568 Spanish attack on Hawkins' and Drake's slaving fleet at San Juan de Ulúa, which left Drake humiliated and craving vengeance; realizing Elizabeth's government refused to back him, Drake privately declared war and pivoted to piracy against Spain's poorly defended treasure colonies. ✦ AI generated

Tom Holland · The Rest Is History · 2026-08-03 · original ↗

starts at this moment · 16:38

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Do you think he really did that? Because it would be foolish surely to to forewarn this guy.

And the impact of this attack is devastating. So four English ships are sunk. Um over 300 um English sailors are killed. 114 are taken prisoner. ... And Drake feels he has massive amounts to prove. ... He takes an amazing course. He thinks, 'Okay, well I will declare war on the Spanish myself.' ... Drake has noted that Spain's defenses in the Indies and on the Spanish main are actually very weak because they are not expecting to be attacked. So Drake is thinking, well, with boldness and good planning, we could take the Spanish completely by surprise. And this is the start of what will become, I guess the most devastating piracy in English history.

verbatim transcript · starts at 16:38

Transcript · around this moment

16:38Hawinson's fleet are in the Caribbean. They think they are trading. The Spanish would say they're smuggling and they're massively blown off course, aren't they? Into I mean they're blown basically to Vera Cruz, which is modern day um Mexico. >> And I think this featured in a series about the fall of the Aztecs, didn't it? >> That's exactly where they go. >> Yeah. Where Cortez met the Amsterus from

16:59Montuma and there was all sort of great banter with exchanging gifts and firing cannons and things. >> All of that. Yes. So this has been called by the Spanish San Juan de Ulua and UA apparently derives from the local name for the Aztecs. So Hawkins and Drake and the slaving expedition, you know, they've sold all the slaves by now and they they've got their money and they're ready to go back home to

17:21England, but they've been blown off course and they have arrived at the place where the Spanish adventure on the Spanish Maine, so that's the kind of the mainland of America. It's where it began. But it is terrible timing because while they're making their repairs, the Spanish viseroy of Mexico turns up with a massive fleet including two huge warships completely bristling with cannon and the English flatillaa is

17:48completely dwarfed by it. So Hawkins desperately tries to kind of sign a truce with the Spanish um you know concealing the fact that he's basically been trespassing on spat and the Spanish sign it but there's an element of treachery in this because the Spanish are just kind of preparing to launch a full-scale attack on this intrusive English fatilla and they justify this on the grounds that um that

18:13the English are pirates and trespassers and criminals which I guess if you're Spanish you know is nothing less than the truth and the impact of this attack is devastating. So four English ships are sunk. Um over 300 um English sailors are killed. 114 are taken prisoner. Lots of these are sent to the galley. There is one poor guy, a man actually not from England but from Cork in Ireland who is

18:37burnt at the stake. Drake and Hawkins both managed to get away but their ships have been very badly mowled in this battle and Hawkins ends up taking a massive financial hit. So all that money that he had made slave trading has basically been lost. And the debacle leaves both men, but I think particularly Drake, feeling very badly bruised. And it has a profound impact on the future course of his life because

19:02Drake is left feeling very humiliated both by the defeat, the fact that the the English have been pulverized by the Spanish, but also because he had escaped the battle before Hawkins did. And so there are rumors that he had been guilty of cowardice. And it seems possible that Hawkins himself believed this. And certainly when they return, there's an element of bad blood between the the cousins. And I think Drake therefore

19:29feels he has massive amounts to prove. And it compounds the sense of anger and outrage that he feels specifically towards the Spanish. And he has a kind of gunslinger in a spaghetti western resolve to be avenged, right? you know, he he he wants to go back and take his anger and his frustration and his sense of shame out on the people that he blames for the humiliation that he'd

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