August 7: Sir Francis Drake (Part 1)

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We have already had reason on this podcast to discuss the fact that people as a rule like simple stories. This is particularly true of our retellings and rememberings of our history. We have a strong tendency to mythologize the figures of the past, making them larger than life–grand heroes or despicable villains. What is particularly interesting to watch is how the same person may be viewed in entirely opposite ways based on the perspective of the person telling the story. One strong example of this, which we don’t have time to fully unpack today, is Chrisopher Colombus. He has been the hero or the villain for various reasons at various stages of history; as recently as the mid 20th century he was almost universally lauded as an intrepid explorer whose courage opened the way to the New World, and he is still held dear by many Italian Americans as a symbol of their heritage; but by 2020 he is almost universally despised as a genocidal murderer and a symbol of the European oppression of the Native population of the Americas. Hero, villain. And of course, neither is entirely accurate. Columbus was a man, nothing more or less, with all the good and the bad that entails. And he was a man of his time, raised with a certain understanding of the world and with cultural mores which are more and more foreign to us. This does not in any way excuse his more horrific behaviours, but it does at least contextualize them. 

It is another such complicated, flawed, and fascinating character of history that we turn our attention to today. To the Spanish he was El Draque, the Dragon, a hated pirate with a price of 20,000 ducats on his head, equivalent to millions of modern American dollars. To the English he was the Sir Francis Drake, savior of England, favorite of the Queen, and heroic swashbuckler whose exploits in the Spanish main were the stuff of legend even within his lifetime. And to some modern historians, he is a greedy opportunist associated with the England’s first dabbling in the slave trade. Somewhere in between, perhaps we can catch a glimpse today of the man behind the myth, recognizing both his virtues and his flaws.

But in order to do that, we have to turn back the clock.

August 7, 1573

Two ships are laboring along under full sail, approaching the southwestern coast of England. 2 days from now they’ll make port at Plymouth Harbor, but today they sight English coastline for the first time in over a year. A trained eye might recognize that the rigging and furnishings of the small ships suggest Spanish make, but they fly English colors, and they are manned by a very small group of barely over 30 men between the two vessels. One can imagine that a ragged cheer goes up as the first man cries out a sighting of their homeland.

The tiny fleet is commanded by Francis Drake, who at this point is probably around 33 years old. He stands at the raised rear deck of one of the vessels, probably already sporting the close trimmed beard and curled moustache which will make him so distinctive in many later portraits, as the hazy coast of England comes into view. It has been a long and difficult voyage, but his first expedition as a privateer has been, all things considered, a great success.

At this point we should take a moment to clarify what exactly we mean by the term privateer. During the early days of colonization of the new world, piracy has become an increasingly serious concern for the new colonial powers who need to ship New World products back to the motherland. Merchant vessels and the so-called “treasure ships” laden with gold and silver mined in the New World are an irresistible lure for private individuals with enough money to outfit a ship and hire a crew. When such an individual operates entirely on their own and for their own benefit, we refer to them as a pirate, a freebooter, a corsair, or any other number of titles. But if a national government gives such a person official authority, by means of a document usually called a “letter of marque,” to commit piratical acts against only that nation’s enemies, then we refer to them as a privateer. And Elizabeth I of England has been giving out letters of marque like candy for the past decade.

The reason for this extensive hiring of privateers is complicated. Elizabeth’s half-sister, generally remembered by the title “Bloody Mary,” had come to the throne after the death first of their father Henry VIII–you know, the one with all the wives–and then his young son Edward, who died of illness after a very brief reign. Henry VIII had begun the English Reformation and created the Anglican Church in order to divorce Catherine of Aragon, his first wife, who had granted him a daughter but no surviving sons. Bloody Mary was that daughter, and unsurprisingly she was raised as a devout Catholic with a deep resentment of her father’s reformation and the divorce of her mother. When she came to the English throne herself, she was determined to undo her late father’s break from the Catholic Church. As part of her reinforcement of pro-Catholic and anti-Protestant policy, she married Philip II, the Catholic king of Spain. She then carried out various purges, including the burning of prominent English reformers at the stake, which earned her the ugly nickname we still attach to her today.

When Mary died childless, however, the throne came to her younger half-sister Elizabeth. Elizabeth had been raised as a Protestant, and she restored and completed the reformation that her father had begun. Philip II of Spain, however, refused to recognize the legitimacy of Elizabeth’s queenship. From his perspective, she was a bastard, as Henry’s divorce of Catherine of Aragon had been illegitimate and thus all his later marriages were adulterous under Catholic church law. Philip claimed that the throne of England was rightfully his, as the husband of the former legitimate queen.

Ever since then, a sort of cold war has existed between Elizabeth’s England and Philip’s Spain. War is never officially declared, but each works to undermine the other as much as possible. And one of the best ways for Elizabeth to attack her former brother-in-law while maintaining a degree of plausible deniability is through the use of privateers who can attack his holdings and his ships in the Caribbean. Any treasure ship that is sunk, or, far better, captured will chip away at the financial armor of Spain.

Enter Francis Drake, and many others like him. But first, let’s turn the clock a wee bit further back to get some background on the privateer’s origins.

Drake was a member of the English lower classes; his grandfather was a tenant farmer on a manor estate, and his father was something of a scoundrel who fled the country to avoid criminal charges when Francis was a young lad. Francis was raised by relatives–the Hawkins family, who owned a number of ships that operated out of the port of Plymouth. The Hawkins were merchants for the most part, but accounts suggest that they were not above occasional piracy, plundering merchant vessels along the coast of France. And by the age of 18, Francis was sailing with the Hawkins fleet.

It was early in this career, under the command of John Hawkins, that Drake was for a time involved in the slave trade. Spain’s colonies and plantations in the New World required a tremendous amount of labor, and the native population had been decimated by their exposure to European diseases over the past seventy five years. Portugal began the trade, capturing Africans from coastal villages or, more and more often, purchasing slaves from the local African rulers, many of whom were happy to take European luxury goods in exchange for enemies they captured in their wars. Portuguese slave ships regularly plied the waters of the Atlantic delivering and selling these slaves to Spanish governors in Central and South America. It was a new trade, and a potentially profitable one. And John Hawkins was always on the lookout for potential profits.

Hawkins sailed his small fleet to the coast of Africa and captured several Portuguese slave ships, then sailed them across the Atlantic to Spanish owned territories. Portugal and Spain had an agreement for the transport and sale of African slaves; Spain had no trade agreements with England, however, meaning that in the eyes of the Spanish viceroy, his trade in the region whether in slaves or other goods was all illegal. As a result, Hawkins had to sell his cargo, human and otherwise, to local Spanish officials who were willing to pay for cheap slaves or other goods while turning a blind eye to technical legality. 

On the second such slave trading voyage, Hawkins, Drake, and the rest of their crew stopped at a Spanish port to resupply with water and repair their vessels after a storm. In spite of the illegality of their trade mission, the English sailors believed themselves to be essentially protected by the truce currently in place between Spain and England, but were still wary. The viceroy, who had received strict instructions to put an end to all illegal English trade in the region, made a pretense of welcoming the English sailors, then launched a surprise attack which left hundreds dead and three of the five English vessels sunk or captured. Drake and Hawkins each managed to escape the ambush, barely, in the two remaining vessels, but had too many crewmen and too few provisions to make the voyage home. They were forced to leave over a hundred men behind, telling them to surrender to the Spanish. The majority of these men eventually were tried by the Spanish inquisition. At least one was burned at the stake, and many of them were sentenced to decades or a lifetime serving as galley slaves on board Spanish ships.

This sneak attack by the viceroy left the young Drake with a burning hatred of the Spanish, whose actions he viewed as treacherous and duplicitous. Much of the rest of his life would be spent in a quest for revenge.

Last year, 1572, Elizabeth I gave Drake a personal commission as a privateer to harry Spanish trade in the Caribbean. Thrilled at the chance to take vengeance against Spain, Drake set out with two small vessels, the Pascha and the Swan. With a total expeditionary force of only 73 men, Drake showed for the first time the shocking confidence and personal ambition which would define his career. His crew would not merely prey upon shipping lanes or raid small Spanish settlements. He set his eyes on Nombre de Dios, a fortified and well-garrisoned Spanish settlement on the Isthmus of Panama. It was the primary port of call for the Spanish treasure fleet; baggage trains of hundreds of mules would bring silver and gold by land to the port, and large storage houses in the town  would hold the treasure until the fleet arrived for loading. Drake hoped to capture the town in a surprise attack, take the storehouses, load his ships, and get away.

The first stages of the plan went quite well. Drake’s men anchored some way off shore and moved towards the town using small rowboats by moonlight, then silenced the guardsman at the artillery batteries along the shore without any alarm being given. Drake then split his group. While half would make a sudden furious attack on the west side of the town, drawing the attention of the garrison, the remainder would follow Drake right into the middle of town to take the Governor’s mansion and the treasure house.

The sudden assault of musket fire in the wee hours of the morning threw the Spanish garrison into utter confusion. The unexpected nature of the attack and the darkness helped the Spaniards to believe that they were being set upon by a much larger force; the reality was that they probably outnumbered Drake’s forces by more than 2 to 1. Nonetheless, the garrison retreated in disarray, and Drake’s forces were able to push into the center of the city and seize the governor’s mansion. There they found large quantities of silver bars, but Drake told his men to leave it. Gold and jewels were far more valuable by weight, and so carrying silver would be a waste of their limited manpower. They moved onwards towards the treasure house.

Then things started to go wrong. Some of the Spanish soldiers had begun to regroup, and a musket shot fired across the town square struck Drake in the thigh. He ignored it, and urged his troops on, not letting them know that he had been injured. When they reached the treasure house, they were met with a massive iron lock. At this point, with Spanish forces gradually realizing the actual size of Drake’s little army and gathering in, things were looking dire. Drake urged the men to break the lock, and with tremendous effort, eventually they did. The doors swung open to reveal…

Nothing. The treasure fleet had come and gone, and the storehouses were empty. At this point, Drake fell into a swoon and collapsed to the ground. Only then did his men realize his injury, and saw that his bootprints in the town square were filled with blood. Pulling their unconscious leader with them, they fled the town empty handed.

Empty handed, but not without having gained a critical advantage. That advantage came in the form of an escaped black slave named Diego. Diego, upon hearing the gunfire as Drake’s attack on Nombre de Dios began, fled his Spanish master’s house and ran towards the sounds of the fighting. He reached the contingent of English sailors who were leading the diversionary attack on the western side of the city, dodging bullets from both sides, and called out to the English that they were in terrible danger and must withdraw. He was aware of the strength of the Spanish forces, and foresaw disaster if Drake’s men were still present at daybreak. As a result, when Drake’s men withdrew, Diego joined them.

Diego helped direct the retreating Englishmen and their wounded captain into regions far from beaten paths, where they met the Cimarrones, as the Spanish called them: a large population of former African slaves who had escaped from Spanish mines or plantations and now fought an ongoing guerilla war with their former masters. These “Maroons,” as the English would come to know them, helped Drake and his men to camp, and gave assistance to them as Drake recovered from his injuries.

In the Maroons Drake found natural allies whose hatred of the Spanish was if anything far stronger than his own. Diego, who could speak in both Spanish and English fluently, was able to act as liaison between the two groups, and from then on they worked in concert. Drake was able to continue minor raids with his ships along the Panama coast, but he was still hoping for a much greater prize; the mule trains carrying gold and silver to Nombre de Dios. Attacking the town again, even with the Maroons at his back, he judged to be foolhardy. But an ambush on the mule train as it made its way to the town would be far less dangerous and nearly as profitable. Unfortunately, it would be some time before the train would come, and it was the wet season. An outbreak of yellow fever devastated the remaining members of Drake’s expedition, leaving just over 30 alive.

With this badly diminished force, the first attempt to ambush a Spanish convoy went poorly, with a drunken member of Drake’s crew firing early and alerting the mule train, which was able to retreat before it could be surrounded. One small bright spot in the failed attempt was that on the journey to the ambush point the Maroon guides brought Drake to a stunning overlook on a ridge from which the whole isthmus of Panama could be seen, from the Atlantic in the east to the Pacific in the west. This was the first time Drake had seen the Pacific Ocean, and he prayed then and there that God might “give him life and leave to sail once in an English ship upon that sea.”

Shortly afterwards, an unexpected ally arrived in the person of a French privateer by the name of Guillaume le Testu. If you know anything about history, you know that the French and the English are rarely on good terms, but le Testu was a Huguenot Protestant, and he brought news of the horrific massacre of French Protestants in the St. Bartholomew’s Day Massacre earlier that year. Philip II of Spain had celebrated the event as a glorious moment of the triumph of Catholicism over the heretics. Thus, le Testu and Drake bonded over a shared hatred of Catholics in general and Philip II in particular, and agreed to split evenly any profits they could achieve through the capture of the wagon train.

In the end, with the help of le Testu’s added manpower and the knowledge of terrain provided by the Maroons, a second ambush was arranged near Nombre de Dios. The wagon train was captured, the guards killed or driven away, with only two casualties; one killed Maroon, and Captain le Testu badly injured. With a matter of hours before the garrison of Nombre de Dios would be alerted and come looking for the train, Drake’s remaining men and le Testu’s French crew leaped into action. The quantity of silver carried by the mules was far beyond what they would be able to take with them; each of the 190 mules of the train, according to Drake’s own account, carried as much as 300 pounds of silver. Fortunately, plentiful amounts of gold and jewels were also present. Drake and his allies gathered as much as they could carry, buried what they could of the rest hoping to reclaim it later, and then had to flee. Le Testu, too injured to walk, remained behind with two of his own crew, and was unfortunately captured by the Spanish before a rescue party sent by Drake could reach him.

Drake split the profits as agreed with Le Testu’s crew, and bade farewell to the Maroons. They asked no share in the gold and silver, but instead for whatever he could spare in iron to make weapons for their ongoing fight against the Spanish; Drake willingly agreed, and broke up several of the smaller ships boats to give their iron fittings over, as well as other weaponry. In particular, he presented the Maroon’s leader with a gold-encrusted scimitar as a thanks for all the help they had given since the disaster at Nombre de Dios.

Over the past months of coastal raids, Drake had managed to capture several small Spanish vessels, but his tiny crew of 30 odd men were barely enough to even manage the Pascha, the larger of the two ships with which they initially sailed to the Caribbean. As a result, Drake filled the Pascha with whatever Spanish prisoners had been taken in the past months of raids, and set them free to make their way back to a Spanish port as best they could. For himself, he split his men between two of the smaller captured vessels and loaded them with loot.

Diego, meanwhile, chose not to remain with the Maroons but to join Drake’s crew and return with him to England. And in fact, Diego will be with Drake throughout his coming adventures. Years from now, a Portuguese pilot captured by Drake on another adventure will note with some surprise that he met on board Drake’s ship a negro who insisted that he was under paid contract with Drake, just like any of the other sailors, rather than being a slave. Diego will be regularly referenced in accounts of Drake’s later voyages. For the next 6 years, the two will be nearly always in one another’s company; Diego turns out to be a capable sailor and an excellent carpenter, but also seems to have served as Drake’s manservant while on board, meaning that he likely spends more time with Drake than any other member of the crew.

And so, as the two captured ships with their cargo of stolen treasure approach the English coast and Drake’s ragged and battered crew sights English soil and cheers, we can readily imagine Diego, now a free man, stands a few steps away from the captain, raising his voice to join them.

This is far from the end of Drake’s story, as you likely know, and is thus far only a hint at the complexity of the man’s character and history. And in fact, two weeks from now, on August 21, we will have opportunity to return to the story of Francis Drake and of Diego, and perhaps gain some further insight into this complicated man and his history. For now, we can at least say this. Drake was courageous to the point of rashness, ambitious, at times arrogant, and possessed a gritty charisma that made members of his crew willing to die for him. At the same time, he was despised by many members of the gentlemanly classes of England as an upstart from a low class family, whose rough manners and lack of care for social graces were a matter of disgust. To the Spanish he was seen as more devil than man, but his treatment of captured enemies is consistently described even in Spanish and Portuguese sources as courteous, even friendly. And then there’s the strangeness of reconciling the man’s early career in the slave trade with the evident mutual respect between himself and the Maroons, and his long connection, perhaps even friendship with Diego.

Nonetheless, his connection to the slave trade have led in the past month to petitions for schools and streets named after him to change their names, and at least one statue of Drake has been taken down.

Drake was neither a pure hero nor a pure villain. He was a man. And perhaps the complexity of his story may remind us that if men are judged on the basis of moral perfection, we’ll find no one worthy of our admiration at all… and a world without heroes is, I believe, a world which has lost something of value. Better to recognize that all humans are, precisely because they are human, flawed; and that praising the good and condemning the flaws need not be mutually exclusive.

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