I told him that England must be good country as there were no slaves there; and he said to me that it was true, they were all freemen in England; whereupon I said that John Hawkins had been engaged in a slaving voyage, and had brought the slaves here to New Spain, and I asked him, how he accounted for this?
—Juan Gelofe, 15721
As it made its way down the Atlantic seaboard in the direction of the Canary Islands, the large English naval squadron must have been an impressive sight. The year was 1595 and the 28 ships and roughly 2,500 men sailing under the divided command of two aging knights—John Hawkins and Francis Drake—represented England’s first large-scale assault against Spain in six years. But as impressive as it surely was to witness, it was a familiar scene. English ships under the command of the nation’s most renowned captains routinely sallied forth to punish the Spanish and cripple their ability to continue prosecuting the now decade-old Anglo-Spanish War by plundering the West Indies. The English were practiced pirates and privateers and had conducted similar expeditions throughout the previous decades, although they typically did so with far fewer men and ships and with a greater commitment to secrecy. Perhaps that would have been a good idea here, for this last great privateering expedition of the sixteenth century would prove to be disastrous in the end. The English would reap few rewards; Drake and Hawkins would both perish; and many ships, soldiers, and sailors would never make it back to England.
The expedition began with a preliminary and fruitless assault on the Canary Islands in early October. With little to show for its efforts, the English fleet then headed across the Atlantic. During the initial planning stages, the English schemed to attack Panama, a familiar strategy by the 1590s, but Elizabeth was reluctant to commit the necessary resources and was worried about robbing the British Isles for an extended period of time of the ships that would defend the shores from another attempted Spanish invasion. Drake and Hawkins were therefore tasked with a less risky and less time-consuming mission: assaulting San Juan de Puerto Rico where, rumor had it, they might capture a crippled Spanish silver ship. But, as in the Canaries, the English once again failed to achieve their objective. Rather than return to England empty-handed, Drake (in sole command after the death of Hawkins off Puerto Rico in November) decided to try to salvage his reputation and do damage to Spain elsewhere. As a man who had faced adversity in the West Indies many times before, Drake was confident that he knew the solution to his present problem. Arriving off the northern coast of South America at Rio de la Hacha in December, Drake steeled himself and his men and determined to relive past glories and yet again embarrass the Spanish on their own turf. To do so, he realized, the English interlopers would need help from those people who had done so much in the past to help the northern Europeans amass wealth and undermine Spain’s ability to defend its American territories. To snatch victory from the jaws of defeat, then, Drake went looking for his old friends, his African allies.2
Englishmen and Africans had been working together in the West Indies, sometimes willingly and sometimes not, for more than thirty years. Thousands of Englishmen sailing in hundreds of ships had passed through the Caribbean since mid-century, during which time they had repeatedly sought out Africans, free and enslaved, for the help they could provide as military allies, translators, intermediaries, and guides. When practicable, the English also took profitable advantage of Africans as hostages and slaves. African agents provided the English with valuable information about Spanish defenses, weak spots in the colonial armor, places where goods could be bought and sold, where ships sailed and provisions might be found, and how to exploit both the land and sea to their greatest advantage. Of course, most Englishmen knew and accepted that the vast majority of black-skinned people in the Americas were enslaved and were primarily of value in the region for their labor. When the English bought and sold Africans or took them hostage and ransomed them back to their owners, they became willing participants in (and endorsers of) the transatlantic slave system. But African peoples were more than simple objects of exchange in the global struggle for power among European nations. Numerous African peoples were actually free inhabitants of Spanish cities and armed for colonial defense. Other Africans, most notably cimarrones (cimarrons), were free by virtue of having run away or rebelled and could be found (though not easily) in the more remote regions of the Spanish Main and, especially, Panama. Africans were everywhere in Spain’s Atlantic world and without them this massive expanse of land and water would have been incomprehensible and largely inaccessible to English merchants, mariners, and privateers. Not surprisingly, then, when Drake was lost in the waning months of 1595 he turned to Africans to lead his expeditionary force out of the morass.
After the English managed their first victory at Rio de la Hacha, the commander had little doubt about how to proceed. First, a member of Drake’s personal entourage, Thomas Maynarde, reported that “we tooke many prisoners Spaniards & negroes, some slaves repairinge to us voluntarily.” According to Governor Manso de Contreras, some of the “Negroes employed at the pearling station … gave Francis Drake information about my plans and where to find our people and your majesty’s treasure.” Once Drake gathered this intelligence, however, he almost immediately ransomed “the whole (except the slaves which voluntarily repayred unto us) … for 24000 peases.” The English turned a tidy profit by selling many Africans back into slavery. At the same time, the English also left the region with scores of Africans who would augment the depleted English forces in their further depredations. Manso de Contreras claimed the English departed with “100 Negroes and Negresses from the pearl station, who for the most part joined him voluntarily.”3 When Drake and his men continued on to Nombre de Dios, in Panama, Drake expected to find more Spanish treasure and even more African assistance, this time in the form of the independent African bands that had so famously aided him in his exploits during the 1570s.
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