Drake's 1572-73 raid on Nombre de Dios succeeded through an unexpected alliance with escaped African slaves, the Cimarrones, who were fierce fighters eager for vengeance on Spain — the first alliance ever made by an English captain with a black military power.
The speaker details how Drake, forewarned of a treasure fleet, allied with the Cimarrones (escaped African slaves) in Panama through the freed slave-turned-right-hand-man Diego. Their combined ambush seized 30 tons of gold and silver, the greatest robbery in English history to that point, despite his near-failure and early rain-stalled attack. ✦ AI generated
Tom Holland · The Rest Is History · 2026-08-03 · original ↗
starts at this moment · 30:16
And these Simones are very proficient at fighting and they're very keen for vengeance on the Spanish. ... It's an absolute marriage made in heaven. ... And on the 1st of April, he launches a second ambush. And this one is a resounding success. ... And they take 30 tons of gold and silver. ... It is, you know, the basically the greatest robbery in the whole of English history up until this point. ... There is this alliance with the Simone. So, as we said, it's the first alliance ever made by a British captain with a black power.
verbatim transcript · starts at 30:16
30:16Nottingham, I'm going to come in and steal all your treasure. >> Do you think he really did that? Because it would be foolish surely to to forewarn this guy. I think he did because he was a he's among other things he's a master of psychological warfare. >> Okay. Yeah. He's trolling him. >> Yeah. Exactly. He's building a a kind of sense of himself as a menacing figure
30:34operating in the shadows who has to be taken seriously. >> Yeah. >> And and as you say, that kind of trolling is something that that makes Drake even at this stage before he's really taken any treasure from the Spanish makes him into a kind of bogey manner, you know, a phantom of the shadows. Well, I mean, not least because he actually does it, right? He actually follows through on his promise.
30:56>> He does. So, how does he pull it off? This amazing kind of heist. And the simple answer is 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
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