UP FROM SLAVERY: DIEGO AND FRANCIS DRAKE

By Dr. John Sugden

This article was originally published in the Sonoma Historian which may be viewed HERE.

© Dr. John Sugden, September 29, 2021. All rights reserved. Printed by permission of the author.

Dr. John Sugden is an internationally distinguished historian who holds degrees from three British universities. His graduate degrees are in the disciplines of Modern History and Social Sciences.  His career has included pursuits as a lecturer, writer,  Senior Research Fellow, and academic editor. 

In addition to penning over 100 articles, Dr. Sugden has also written several books which include: 

•  Sir Francis Drake (1991)

•  Tecumseh, A Life (1998) Winner of the Distinguished Book Award of the Society for Military History

•  Blue Jacket, Warrior of the Shawnees (2000), Winner of the Ohioana Prize

•  Two volumes of Nelson (2004, 2012), Sunday Times biography of the year

This detail of the Drake jewel of the Drake jewel, a prized possession of Sir Francis Drake, is curated and displayed at the Victoria and Albert Museum in London, England. The sardonyx cameo shows a white European side by side with a black African.

Image courtesy of Steve Wright

In the Victoria and Albert Museum in London you can see one of the most beautiful and surprising of all English artefacts.

It is a jewelled locket. Inside a cameo of sardonyx displays the profiles of two adjacent faces, unshaven, and looking ahead, standing side by side. One of the subjects is a white European, an Englishman or possibly even a woman. The other is a black African. There is no suggestion that one figure is superior to the other. They stand side by side, as equals, allies perhaps, or friends.

It is a strikingly modern image, and a powerful one, even today in the twenty-first century. It radiates the spirit of racial equality which we rightly enshrine. But remarkably the image is actually more than four hundred years old. It is an Elizabethan locket, made in the 1580s, and in it there is also a portrait of the reigning monarch, Elizabeth I, probably by the famous miniaturist, Nicholas Hilliard. The locket was presented by the Queen as a New Year’s Gift to one of her most trusted subjects, and the image of the white and black man in harmony was obviously deemed to be pleasing and meaningful to the recipient. It represented something fundamental to that person.

One might have thought the recipient was some diplomat, ambassador or perhaps even a humanitarian scholar, but therein is the surprise.

The recipient was none other than Sir Francis Drake, the great seafarer, and the locket has always been known as ‘the Drake jewel’. Drake certainly prized it, and is seen wearing it in the two portraits of him that we now believe were painted by Marcus Gheerarts the younger in 1591 and 1594. His wife, Elizabeth, Lady Drake, also wears the locket in her standard portrait, a work of George Gower, the Serjeant Painter to the Queen, done in the late 1580s. Truly a prized possession, the Drake jewel it is one of the few relics of the admiral that survives today, and its image is widely available on internet sites.

The locket spoke to something that was once widely acknowledged: that Francis Drake stood up for black Africans and Native Americans.

As the Doge of Venice was informed in April 1586, Drake “behaved with such humanity to the Indians and Negroes [in the West Indies] that they all love him and their houses were open to all English.” An exaggeration no doubt, but Drake did respect these peoples, and spoke forcibly of the cruelties and wrongs done them, urging the English to unite with them in their struggle against Spanish oppressors. Alan Ereira, researching a television documentary as late as the 1990s, was surprised to find Native American communities in Central America who still venerated Drake as a hero.

Back in Jacobean England, one Thomas Fuller, a minister acquainted with some of those who had known Drake, used the admiral as the template for his ideal sea-captain when he wrote The Holy State published in 1642. “In taking a prize, he most prizeth the men’s lives whom he takes,” he wrote, “tho’ some of them may chance to be Negroes or Savages [Native Americans]. ‘Tis the custom of some to cast them overboard ... but the murder is not so soon drowned as the men. What, is a brother by the half-blood no kin? A savage hath God to his father by creation, though not the church to his mother, and God will revenge his innocent blood. But our captain counts the image of God nevertheless his image [if] cut in ebony as if done in ivory, and in the blackest Moors he sees the representation of the King of Heaven.” White or coloured, all were the creations of the same God, and therefore to be respected.

But for many today the locket, with its message of racial harmony and cooperation, poses a riddle. It seems curiously at variance with the fact that Francis Drake, as a young man in his early or mid-twenties, had served on slave ships owned by his relative, John Hawkins. We know that he made two voyages for Hawkins in 1566 and 1567, taking black slaves to the West Indian islands for sale to the newly established Spanish colonies. We actually know little of Drake as a man at this time, except that he was such “a great Lutheran” that he was able to persuade older ship-mates to embrace the new Protestant faith, and to teach them the Paternoster and the Creed. He did not, as far as we know, have strong opinions bout race or slavery, and rose to be a junior officer in the last of the two Hawkins ventures. But his connection with slaving, brief as it was, makes a striking contrast with the imagery of the locket, and the reputation Drake later gained as a champion of coloured races.

What, then, had changed? What happened to make turn this young man on the slave ships of the 1560s into the wiser head recognized by the likes of Queen Elizabeth and Fuller as a friend and supporter of black and Native American peoples? It was a surprising transition, especially in that age driven so forcibly by profit, violence and religious certainties.

We must beware of judging our ancestors according to knowledge and precepts that lay centuries in the future, and which they could never, therefore, have known. As the novelist L. P. Hartley famously wrote, “The past is a different country; they do things differently there.” In the sixteenth century politics and warfare, even among European nations that deemed themselves civilized, routinely involved torture, savage public executions, and the wholesale slaughter of resisting armed garrisons. Religion sharpened the divisions, as the St. Bartholomew’s Day massacre in France, the Marian burnings in England, Spain’s ferocious attempts to suppress the Protestant Netherlands, and the struggle between Christians and Muslims in the Mediterranean vividly illustrated.

When Europeans went abroad there was little regard for the indigenous peoples. The Portuguese cut an empire out of the east, brutalizing those who opposed them. Spain did likewise in central and south America, plundering, enslaving and exterminating by disease as well as by violence Aztecs, Incas, Arawaks and Caribs as they did so. To meet the shortage of labour in their mines and plantations the Spaniards imported African black slaves, using Portuguese, some French, and in the 1560s English slavers.

There was relatively little criticism of this. In Spain Bartolome Las Casas raised an influential voice of protest, mainly in defence of the Native Americans, but in England, then a minor player in overseas expansion, little debate or interest was shown in the plight of Indians or African slaves as late as the 1580s.

Many writers who talk about the Anglo-Spanish conflict in the later sixteenth-century Caribbean forget this older and bitterer struggle that was still going on in some regions. In Drake’s day the Lokono Indians were still resisting the Spaniards on the mainland, in what is now Venezuela and its neighbouring states, while communities of black Africans, known as Cimarrons, escaping from Spanish settlements and living off the country, bore a fierce hatred of their former masters.

In 1570, however, Drake began to intervene in this struggle, appearing with relatively small English forces bent upon making reprisals upon Spain for the treacherous attack upon Hawkins’s trading fleet at San Juan d’Ulua in Mexico the previous year. Drake was not the first corsair to visit the West Indies. The French had been involved in similar guerrilla warfare, but Drake was the first to realize the significance of the concomitant black and native struggle, and to cement an alliance with the Cimarrons.

The story is attracting some modern scholars, but Irene Wright gave us a wealth of essential documents as long ago as 1932, including a reprint of the classic English narrative, Sir Francis Drake Revived, written at Drake’s behest in the 1590s. It requires us to consider the crucial role played by a black rebel known only as Diego.

Sadly, we know very little about Diego. His was a remarkable life, so worthy of a historical novel or motion picture that I once tried to interest a black dramatist in Chicago in producing a script. One supposes that Diego had been born in West Africa and shipped as a slave to the West Indies, probably by Portuguese slavers. His master in the New World was a professional soldier and merchant, Captain Gonzalo de Palma, who variously resided in Panama and Nombre de Dios. Situated on the Caribbean side of the isthmus, Nombre de Dios was one of the terminals for the Spanish treasure shipments that passed between the New and Old Worlds, and Palma was much involved in security. In 1573 he was appointed captain-general and mayor of Nombre de Dios, and in 1592 would begin a three-year stint as the governor of Costa Rico.

Diego did not enjoy his service with Palma. He appears to have been used as a spy or undercover agent to infiltrate or discover intelligence about the Cimarrons who were resisting the Spaniards as best they could. When Drake attacked Nombre de Dios in July 1572, Diego seized his chance. He fled to the English. Communicating through imperfect Spanish, it was Diego who pointed out to Drake the uses of the Cimarrons, who both knew the country and the movements of the Spaniards. He also knew how they might be contacted. The policy was not without personal risk. Diego explained that he had “betrayed” the Cimarrons several timesin the past, and needed Drake’s protection to proceed.

This was a turning point. Drake had already resolved to make use of the Cimarrons. On arriving in the West Indies he had taken two Spanish ships, and deliberately released their black slaves and set them ashore. “Our captain,” says the narrative, “willing to use those Negroes well...set them ashore that they might perhaps join themselves to their countrymen the Cimaroons [sic] and gain their liberty if they would.” At this time, too, Drake was grasping the essence of the race war in the West Indies, “by reason of their [Spain’s] cruelty.” He was also cultivating the Native American communities, treating them fairly and “giving content and satisfaction of the Indians.” But it was the alliance with the black Cimarrons that paid dividends to both parties.

The evidence suggests that the relationships between the Drake and the Cimarrons were exceptionally strong. Under their leader, Pedro Mandinga, the Cimarrons “did us continually very good service, being unto us ... intelligencers, to advertise us; of guides in our way to direct us; of purveyors to provide victuals for us; of house-wrights to build our lodgings; and had indeed able and strong bodies, carrying all our necessaries; yea, many times when some of our company fainted with sickness of weariness, two Cimaroons would carry him with ease between them, two miles together, and at other times, when need was, they would show themselves no less valiant than industrious, and of good judgement.”

Through this vital assistance, Drake was able to ambush Spanish mule trains carrying treasure across the Isthmus of Panama to Nombre de Dios, and achieve his first major successes. It was unquestionably a formative experience. Drake listened to the grievances of the Cimarrons. One of their former Spanish masters was said to make cruel use of a hundred or so slaves in his mines.

When the time came for the English to depart, they felt greatly attached to their allies. “Thus,” says the narrative, “with good love and liking we took our leave of that people.” As for Diego, Drake commemorated his continuing usefulness by naming a river (Rio Diego) and a fort (Fort Diego in the Gulf of San Blas) for him. Diego chose to remain with him when he returned to England. He thus lived as a free man in Elizabeth’s England, and was likely presented at court.

The Spaniards were rightly alarmed by these developments. “This league between the English and the Negroes is very detrimental to this kingdom, because being so thoroughly acquainted with the region, and so expert in the bush, the Negroes will show them methods and means to accomplish any evil design they may wish to carry out and execute,” the Municipal Council of Panama wrote the Crown on 24 February 1573. “These startling developments have agitated and alarmed this kingdom. It is indeed most lamentable that the English and Negroes have combined against us.”

Such concerns were not unfounded, for Drake’s reliance upon the Cimarrons underpinned his next great venture, which ultimately led to his circumnavigation of the world in a journey of some 50,000 miles, the longest single voyage yet accomplished by anybody.

Diego went with Drake in his flagship, the Golden Hind, and was a significant asset. Backed by members of government, including the Queen, Drake intended exploring the Pacific coasts of America, and raiding the unwary Spanish ships and settlements there, but his greatest quandary was how he might safely return. One possibility was to seek the legendary Northwest Passage that no one knew for certain existed, but another was to escape by means of the Isthmus of Panama, relying again upon the assistance of the Cimarrons. In that event Diego would have been an important intermediary.

Drake’s raid was accomplished, as every schoolboy once knew, and an immense treasure taken, fortunately without the cost of a single Spanish life. The prisoners that Drake took in 1579, however, testified both to his preoccupation with the Cimarrons, and his great regard for them. “Captain Francis,” said Nicholas Jorje, “says that he loved them, and that he spoke well of them, and every day he asked if they were at peace.” Another witness, San Juan de Anton, who commanded the richest of Drake’s prizes, deposed that the English assured him that “these Negroes [the Cimarrons] were the brothers of Captain Francis, who loved them dearly.” Anton also noticed Drake’s policy of freeing black slaves he found on Spanish ships, unless, that is, they specifically wished to remain with their masters. I cannot think of another Elizabethan who spoke of coloured peoples in this way.

His treatment of the indigenous peoples on this voyage was also in marked contrast to the brutalities visited upon them by Columbus, Pizarro, Cortes and Da Gama, or more latterly many English adventurers. In 1585, for example, Sir Richard Grenville (he of the Revenge) destroyed a Native American village in Virginia after the theft of a silver cup. When Indians stole Drake’s cap, among other wonders, on his outward voyage, the captain “would suffer no man to hurt any of them.” His forbearance and motives were more evident in later encounters. In defence of the lives of his men Drake twice resorted to arms, but only as a final resort. When two of his men were killed and others wounded, one himself, during a landing on Mocha, off the Chilean coast, in November 1578, Drake refused to allow his men to fire upon the natives with the ship’s artillery in retribution. “The cause,” he explained, “was no other but the deadly hatred which they [the Indians] beare against their cruel enemies the Spaniards, for the bloudy and most tirannous oppression which they had visited towards them.” In his view the natives had simply taken the visitors to be Spaniards.

Where possible, Drake followed a policy of leniency and friendship, exemplified, perhaps, in his relations with the Native American peoples who greeted him when his ship refitted in what he called Nova Albion. Anthropologist Robert Heizer, in Elizabethan California, is one of several scholars who have described this important episode. As James Cook and others would demonstrate two centuries later, relations between unknown and culturally diverse peoples were pregnant with uncertainty and potential violence, but in Drake we see some of the earliest attempts to understand and identify with native communities.

It is possible, coincidentally, that the attack on Drake’s boats at Mocha cost the life of the estimable Diego. According to one account he was among those mortally wounded by the natives. The deposition of San Juan de Anton, however, might be read as establishing that Diego was still alive several months later. It is not clear when or how Diego died, but he does not appear to have survived the voyage to become the first black circumnavigator. Nevertheless, his career would have seemed astonishing to his fellow villagers in Africa. He had survived the horrors of slavery, and escaped from Panama to achieve several years of freedom in England, viewing spectacles he could never have imagined. Not least he had been the associate of one of the most dynamic figures of the age, and helped mould his career and opinions. In Drake’s mature views about black and native peoples we can surely see echoes of his many conversations with Diego.

That Drake continued to argue these beliefs seems certain. That alone would justify the Queen’s gift of the Drake Jewel, with its symbol of the alliance of black and white, a symbol that Drake proudly wore. As late as 1593 he was apparently singing the same song. Drake became a member of the English parliament, but although he was active in committee work he is only known to have made one speech. Supporting increased expenditure on defence, Drake then “described the King of Spain’s strength and cruelty, where[ever] he came, and wished a frank aid to be yielded to withstand him.” Given Drake’s familiarity with the Americas, one must assume that he was adverting once again to what he had seen there, and to what Diego and others had told him of the Spanish treatment of blacks and Native Americans. If so, this would be the first time that the plight of coloured races was ever raised in the English parliament.

In a period of rapidly deteriorating relations between Catholic Spain and the Protestant powers of Europe, Drake’s views were not unattractive. The idea was growing that England might have need of allies wherever they were to be found. Elizabeth’s locket suggests that she was receptive to an alliance between black Africans and the English. She certainly began to court the Muslim powers of Turkey, Morocco and Persia, and sent an ambassador to Constantinople. Drake, who, some Spaniards complained, treated all nationalities and races as equals except the Spanish, fitted this strand of diplomacy. He was reported to have sent presents to his opposite number in Turkey, and even to have considered continuing the fight from Turkey if England fell in combat.

When Drake sailed to the West Indies again in 1585, it was to lead a fleet west to attack Spain’s major cities. We need not dwell on his capture of Santiago in the Cape Verdes, Santo Domingo and Cartagena in the West Indies, and St. Augustine in Florida, except to say that on this expedition Drake elevated his ideas about liberating slaves of every race and persuasion to a strategically significant level.

Drake began liberating slaves in the Cape Verdes, and continued the practice in the West Indies, destabilizing some of the enslaved communities. At Cartagena Muslim galley slaves fought themselves free and jumped into the sea to swim to the English boats and ships. When slave masters of Cartagena offered to pay Drake a ransom for the return of those slaves who had joined him, he refused unless the slaves themselves were anxious to resume their former status.

Records show that Drake welcomed the runaways, and looked after them. He issued “ageneral commandment, given for the well usage of ... Frenchmen, Turks and Negroes” who joined them, and assembled several hundred freed slaves, black Africans, Moors, Turks and some Native Americans, by some accounts over a thousand. We do not know what happened to all of these slaves. Some may have been released to form their own free communities, in the manner of the Cimarrons, and others landed at the English colony of Roanoke. Some came home to England, and theQueen had a hundred of the Muslims, all furnished with new clothes, to be given free passage to Turkey to be repatriated.

There was also the sad fate of the black messenger that Drake sent to carry his words to the Spaniards at Santo Domingo. He may have been a former slave, because he likely had a command of Spanish, but he proceeded under a flag of truce with a message from Drake during negotiations between the belligerent parties. A Spanish soldier, presumably affronted by the use of a black boy, struck him down with a lance. The boy struggled back to his lines and died at Drake’s feet.

The incident provoked the most violent act of Drake’s career. He was, on the whole, a merciful man. Even the governor of Santo Domingo found Drake “alert, restless, well-spoken, ambitious, vainglorious, but generous and liberal; not a cruel man.” And another Spanish official, Don Alonso de Sotomayor, the Captain-General at Panama who successfully repulsed Drake’s forces ten years later, conceded that his adversary was “very courteous and honourable with those who surrendered, of great humanity and gentleness, virtues which must be praised even in an enemy.”

Well, usually. But on this occasion Drake hooked out two Dominican friars from his prisoners and hanged them in retaliation. He promised to execute more prisoners if the murderer of his envoy was not punished, and the Spaniards put the guilty soldier to death themselves. Nothing like this explosion of anger had been seen in Drake before. Obviously he took the attack on his envoy as a personal insult, but the episode tells us that to Drake this black boy’s life was as precious as any other.

In his final voyage, undertaken in 1595 when his powers were failing, Drake missed the Cimarrons, but they had been a significant force in his career, and the evidence we have suggests that he appreciated them and understood his part in their own battle for survival. Despite his humble origins, Drake was a complex man in a peculiarly difficult time of religious, racial and imperialist rivalries. He has not been well served by writers who have represented him in simple terms, and few historical figures have been more damned and sainted. His portrait needs to be painted in subtler shades.

He was an ambitious, decisive and determined man driven by glory and gain, but also his god and country. He was ruthless when needs arose, but among the qualities that made him “a fearful man to the king of Spain” were other, gentler, traits. Those who knew him said as much. Thomas Fuller was one. “We will not justify all the actions of any man,” said he, but “for the main we say that our captain was a religious man toward God and his houses (generally sparing churches where he came), chaste in his life, just in his dealings, true of his word, and merciful to those under him, hating nothing so much as idleness.”

But Fuller was an Englishman, and perhaps therefore, by some lights, not to be believed. So let us ask a German observer who met Drake at court for his assessment. As quoted by the late David B. Quinn, who, if he had completed his research might have given us the best biography of Drake, he said, “if I am any judge... [Drake] seems destined by the Good Lord to achieve great things: perceptive and intelligent by nature, his practical ability [is] astonishing, his memory acute, his skill in managing a fleet almost unique, his general manner moderate and restrained, so that individuals are won over and gripped by affection for him. He easily evokes obedience from soldiers and sailors, and consequently if he is compelled to be severe, such is the fairness with which he acts that all resentment or even hatred soon dies away. I say nothing about his magnanimity; and about his learning, experience, and technique in navigation, which events themselves have made abundantly clear.”

Today there are those who seize upon Drake’s early service on slave ships to damn him as a white supremacist, or whatever else may fashionably be used to damage his standing. But it is hardly fair to judge people by what they were in their younger days, when they had not had the time to show what they were capable of becoming. Hopefully, we grow and learn, and we are most faithfully reflected by what we become, and what life has taught us, than what we were at the beginning.

There is much that can fairly be said against Drake, but when compared with the other explorers, soldiers and sailors of his time, his record with black and Native American peoples is unusual, perhaps remarkable. Drake was an Elizabethan, not a modern moralist. He lived more than four centuries ago. But much of what he said and did about tolerance, respect and affection for coloured races seems remarkably modern. He was the nearest the Elizabethans got to a significant champion of these people, and the nearest they got to an abolitionist in his attempts to liberate and sometimes repatriate slaves who came within his power. With the help of an almost forgotten black man known only as Diego, and perhaps also a Cimarron leader named Pedro Mandinga, he had seen and understood something of a world few Englishman knew.

Drake arouses strong passions. He always has, and probably always will, and given the amount of misinformation propagated about Drake, the confusion is understandable. But I believe that most fair-minded people will draw their own conclusions. We have enough evidence to conclude that all those years ago Drake stood up and demanded freedom and respect for Indians and blacks. Now, perhaps, at this time of introspection, it is time to stand up for Drake.

Further Reading

• Umer Faruq Abd-Allah, “Turks, Moors and Moriscos in Early America: Sir Francis Drake’s Liberated Galley Slaves and the Lost Colony of Roanoke,” NAWAWI Foundation Series (2010), 1-43.

• Kenneth R. Andrews, Drake’s Voyages (1967) Jerry Brotton, This Orient Isle: Elizabethan England and the Islamic World (2015).

• P. E. H. Hair, “Protestants as Pirates, Slavers and Proto-Missionaries: Sierra Leone 1568 and 1582,” The Journal of Ecclesiastical History, XXI (1970),203-24.ˆ

• Lewis Hanke, Aristotle and the American Indians (1959)

• Robert F. Heizer, Elizabethan California (1974)

• Miranda Kaufmann, Black Tudors (2017)

• Nabil Matar, Turks, Moors, and Englishmen in the Age of Discovery (1999)

• J. H. Parry, The Age of Reconnaissance (1963)

• Ruth Pike, “Black Rebels: The Cimarrons of Sixteenth-Century Panama,” The Americas, LX (2007): 243-66.

• David B. Quinn, “Turks, Moors, Blacks and Others in Drake’s West Indian Voyage,” Terrae Incognitae,XIV (1982), 97-104.

• Cassander Smith, ‘Washing the Ethiop Red’: Black Africans and English Anti-Spanish Sentiment in the Early Atlantic World (2016).

• John Sugden, Sir Francis Drake (2006 edition)

• Irene A. Wright, editor, Documents Concerning English Voyages to the Caribbean and the Spanish Main, 1569-1880 (1932)

© Dr. John Sugden, 2021. All rights reserved. Printed by permission of the author.