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AnecdoteVideo · 31:20 — 35:45

Drake's most spectacular heist — the ambush of the Spanish silver train at Nombre de Dios — succeeded because he allied with the Cimarrones, escaped African slaves who knew the terrain and were eager for vengeance against the Spanish.

After a failed direct assault on Nombre de Dios, Drake allied with escaped African slaves called Cimarrones, who were expert fighters and familiar with the jungle. With their help, he ambushed the mule train carrying silver from Panama, making off with 30 tons of gold and silver — the greatest robbery in English history up to that point. ✦ AI generated

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

starts at this moment · 31:20

He finds some very unexpected allies. And Drake is introduced to these allies by an African um who's been called Diego by the Spanish. He's a slave who had defected to the English during their raid on Nios. and Drake adopts Diego as a crew member and the two men get on tremendously well. ... Diego reveals that in the heights above Panama, there are African outlaws, escaped slaves called Simones. And these Simones are very proficient at fighting and they're very keen for vengeance on the Spanish. So in every way they're just the kind of guys that Drake wants to make friends with. It's an absolute marriage made in heaven. ... early in 1573 he is brought the news that he's been waiting for. The Spanish treasure fleet has arrived in Nomad Dios um ready to pick up a vast consignment of silver that is in Panama ... And on the 1st of April, he launches a second ambush. And this one is a resounding success. There are no kind of drunks spoiling the surprise. And they take 30 tons of gold and silver. And that is such a hall that half of it actually has to be buried because it's too heavy to be transported.

verbatim transcript · starts at 31:20

Transcript · around this moment

31:24well. Um, so Miranda Calfman, who wrote a great book on black tutors, uh, Diego is one of the, uh, the 10 black tutors in that book. Um, and the friendship between Drake and Diego seems to have been a very close one. Um, and in fact, um, in his book, John Sugdan points out that in the official narrative of the voyage, the one we've been quoting, Diego is mentioned, um, more than any of

31:48the other seaman on either ship in, uh, Drake's expedition, and he pretty much ends up as kind of Drake's right-hand man because he reveals that in the heights above Panama, there are African outlaws, escaped slaves called Simones. And these Simones are very proficient at fighting and they're very keen for vengeance on the Spanish. So in every way they're just the kind of guys that Drake wants to make friends with. It's

32:19an absolute marriage made in heaven. And for the Spanish, of course, it is an absolute disaster. And as an official in Panama, you know, the Spanish very rapidly become aware of this alliance between the Simones and and Drake's Englishmen. This league between the English and the Negroes is very detrimental to this kingdom because being so familiar with the region and so expert in the bush, the Negroes will

32:41show them methods and means to accomplish any evil design they may wish to carry out. And Drake does absolutely have a design because early in 1573 he is brought the news that he's been waiting for. The Spanish treasure fleet has arrived in Nomad Dios um ready to pick up a vast consignment of silver that is in Panama on the Pacific side of the ismas and this is about 60 mi away

33:11um you know along this kind of mule trail and this treasure has been kept there because the Spanish assume you know it'll be more secure there's no way that anyone could attack it actually in Panama but Drake's plan is to um ambush the mule train that will be bringing the silver from Panama. And so that February he goes with the Simones up into the heights above the mule train to try and

33:34kind of um work out the lay of the land. And after 4 days in the wild, they come to a great tree standing on a very high hill. And the Simone have cut steps into the side of the the the trunk of the tree. And at the top of the tree, there's a kind of treehouse, a viewing platform. And Drake climbs up the steps and he gets to this viewing platform.

33:54And from it he is able to see the Pacific as well as the Atlantic. So it's in the um the Keats poem. He and all his men are kind of looking at each other. Unbelievable. And Drake when he sees the Pacific something that no Englishman has ever seen before to quote the the record. He bought Almighty God of his goodness to give him life and leave to

34:18sail once in an English ship in that sea. I mean it's very Drake. >> Yeah. And actually it's a I was about to ask is he the first Englishman to see the Pacific. Of course loads of Spaniards have seen it but it's a sign of how England has been locked out of so far the kind of um exploration of the new world >> and everyone in Europe only the Spanish

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