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Pirate to Admiral: Sir Francis Drake

By Wade G. Dudley
4/4/2018 • Military History Magazine

Sea Dog Francis Drake battled, looted and bought his way from scourge of Spain to Queen Elizabeth’s favorite commander.

“That which we call a rose / By any other name would smell as sweet,” wrote William Shakespeare in the 1590s. Perhaps a well-known contemporary of the great playwright heard those words shortly before embarking on a last voyage in 1595 to scourge the Spanish seas and soil of the New World. If that bold fellow (perhaps in company with his queen, Elizabeth of the Tudors) indeed found the time to hear Master Robert Goffe of the Lord Chamberlain’s Men utter the fair Juliet’s lines, it is doubtful he engaged in literary analysis or deep philosophical musings. Sir Francis Drake had much time for plunder but little time for tropes, thus he would have missed a fascinating corollary to Juliet’s utterance: Does he, whom others name a pirate / By any other name smell still as foul?

Piracy is a nasty word that reeks of death and misery. Seaborne theft has plagued humankind as long as written records have existed—and probably long before. It is not difficult to envision a swarming horde boarding a log raft on a nameless river, stone weapons rising and falling, bodies tumbling over the side, and goods and captives bundled ashore by new owners to be traded, used or ransomed. The pattern is firmly established in written records, from the depredations of the Sea Peoples of the Mediterranean some four millennia ago to those of modern-day Somali pirates. Wherever and whenever a power void appears, banditry—piracy on the world’s waterways— follows. From urban streets to the Central Pacific, predators multiply in times of local, national and international stress as central authorities find themselves distracted and unable to provide security for their citizens. Too frequently this stress spawns a moral laxity that foments even more such brigandage, as desperate people abandon established scruples in the name of survival (hunger and fear create markets and havens, as well as pirates). And such laxity can become common practice—even for entire governments.

Sometime around 1540, Francis Drake, the man who would become the world’s greatest pirate, squalled his way into an England torn by the religious upheaval gripping Christian Europe. After centuries of war with Muslims, the Church of Rome had fractured. Protestants (those who protested a church grown plump and lax as an institution) flourished on the continent, honing both words and swords after Martin Luther focused existing discontent with his Ninety-five Theses on the Power and Efficacy of Indulgences in 1517. In 1534 Henry VIII broke with papal authority and made himself head of the Church of England, though his decision likely had more to do with considerations of dynasty (and perhaps a few lascivious thoughts) than spiritual musings. Granting himself an annulment the Pope had refused to give, Henry set aside Catherine of Aragon (and their daughter, Mary) for the nuptial delights of Anne Boleyn and the hopes of a son to continue the Tudor dynasty. Alas, Anne, too, bore only a daughter, Elizabeth, for the king. A frustrated Henry sent Anne to the block on trumped-up charges in 1536, marrying Jane Seymour almost before the headsman could clean his sword. Henry finally had his son, Edward, in 1537, but lost Jane to complications from childbirth. Unfortunately for the Tudor dynasty, Edward outlived his father by little more than five years, dying childless at the age of 15. Unfortunately for Protestants, and for a young Francis Drake, Mary Tudor ascended the throne of England vowing to restore Catholicism to the land, thus fanning the embers of religious discontent.

In 1549 the Protestant family of a young Drake fled their Devon farm as Roman Catholics rebelled against King Edward’s theological reforms. The family lodged in an old naval hulk, forging the future pirate’s relationship with the sea. His early years are hazy, as the common-born are not marked for glory, much less for the annals of history. Either Francis found himself apprenticed to the captain of a local coaster, which his master eventually bequeathed to him (Drake reportedly sold it to purchase a place in an expedition to plunder the New World), or his father fostered Francis to the home of William Hawkins of Plymouth, where Francis learned the art of plunder from experts.

The Hawkins family owned a small trading fleet that followed the winds and markets throughout the eastern Atlantic. When trade dwindled, as it often did in those troubled times, the clan turned to small-scale piracy. By 1558 Drake was sailing with the fleet under the command of William’s son, John Hawkins. In his years with the Hawkins family, Drake learned the key elements of a new trade: weaponry, ship-handling, logistics, navigation and leadership. He also learned that few Englishmen questioned the provenance of plunder, especially after Bloody Mary’s death and the assumption of the throne by a thoroughly Protestant Elizabeth in 1558.

Much has been made of Elizabeth I, the Virgin Queen of England, and she merits every accolade. During her reign, she battled dissent within her kingdom, a daunting enemy in Philip II of Spain, papal minions, countless suitors seeking to replace her on the throne and the obvious fact she was “only” a woman. Survival of self and kingdom forced Elizabeth to use every tool at her disposal, including piracy. Pressed by a treasury filled with more cobwebs than coppers, Elizabeth gave her “Sea Dogs”—pirates such as the Hawkins clan and their fosterling, Francis Drake—a wink and a nod as they set their caps at Catholic towns, ships and even mules in the New World. Rather than the (debatable) moniker Virgin Queen, perhaps the title best suited to the great Elizabeth is the Pirate Queen.

Though the Hawkins family practiced petty piracy during the reign of Mary, they did so circumspectly. Preying upon the Catholic mariners of Europe while living under a Catholic Queen of England threatened to leave one’s life in suspension—by the neck, until dead. Then, in 1562, Elizabeth unofficially sanctioned an expedition, under John Hawkins, to the shores of Africa and the New World, aimed at challenging the Spanish monopoly on the slave trade between the regions.

With three or four vessels, Hawkins raided or traded for slaves along the Guinea Coast while helping himself to any removable loot. When the slaves crowded his holds, he pressed a Portuguese merchantman into service to carry extra bodies. Placing nonliving plunder in his smallest vessel, Hawkins dispatched it to England; Drake, apparently a much-trusted seaman, was aboard. Hawkins then sailed with the remainder of the fleet for the West Indies. There, he traded his slaves for local riches. Wherever Spanish officials refused to trade with the English (as ordered by Philip II), Hawkins seized hostages or the town itself, leaving only when the Spaniards paid a ransom (often equivalent to the number of slaves Hawkins would conveniently abandon near the settlement—an obvious ploy by all parties to circumvent Spanish law). In September 1563, Hawkins returned to England, holds empty of slaves but full of wealth from the West Indies.

The immense profits enjoyed by investors in the 1562– 1563 voyage particularly impressed the queen. So, despite increasing protests from Portuguese and Spanish ambassadors at her court, Elizabeth invested in Hawkins’ next voyage. Her stake, the 700-ton ship Jesus of Lubeck, served as Hawkins’ flagship when he sailed for Africa and the West Indies in October 1564. Drake again sailed with him, eager to learn and eager to profit. This extremely successful voyage taught the young seaman the fine art of piratical diplomacy (talk, ransom, shoot only if necessary), as well as the location of vulnerable Spanish towns and such Protestant havens as the Huguenot settlement at Fort Caroline on the Rio de Mayo. He may also have met another group of potential allies, the negros cimarrones, escaped slaves living harsh but free lives in the jungles of Central America.

Upon his return from this successful voyage, Hawkins began to plan another. Elizabeth, well pleased with the return on her investment but pressured by Catholic diplomats upset with the increasing Protestant piracy in the Caribbean, could not invest in the new voyage. Instead, she levied a very public £500 bond on Hawkins’ expedition, forfeitable should any of his ships enter the waters of the West Indies. This assured the Crown a cut of the profits and presaged a favored concept of modern-day politicians—“plausible deniability.” Unfortunately for Hawkins and his investors, the 1566–1567 expedition, commanded by a family relation, turned so little profit that forfeiture of the bond erased most of it. Drake, serving as an officer on the flagship, saw firsthand that profit margins on the sale of slaves were decreasing as Spanish resistance to English encroachment increased.

Hawkins, appalled at the small return and as distraught as his queen at Spanish attempts to close the West Indies to English trade, immediately organized a new expedition. Elizabeth contributed two ships to the fleet: Jesus of Lubeck and the similarly sized Minion. Four smaller vessels completed the force, with Drake set to enjoy his first command, the 50-ton Judith. Unfortunately, there was little to enjoy. Plagued by fever and near mutiny (Hawkins even engaged in a knife fight with one of his sailors), the expedition found slave markets closed to them along the African coast. They had to raid inland to capture their own slaves, and even then Hawkins found few willing buyers in the New World. King Philip II had put backbone into his West Indies dominions, one built of new forts, guns, garrisons and warships. After fighting bloody actions at Rio de la Hacha and Cartagena, Hawkins decided to return to England in October 1568, despite the dozens of slaves and scant plunder in his holds. But he had waited too late, and a hurricane smashed into the fleet, blowing it into the Gulf of Mexico. With no available haven, Hawkins seized and fortified the Spanish town of San Juan de Ulúa (near modern Vera Cruz, Mexico) while his ships were repaired. There, a Spanish fleet found them. An attack by fireships escalated into a major battle, and only Drake’s Judith and Minion, with Hawkins aboard, managed to escape. Separated by a storm, each ship wended its way to England, arriving with little in the way of plunder and less then a quarter of the more than 400 Englishmen who proudly left Plymouth the prior year.

Drake had learned the bitter taste of failure. He may also have languished in Elizabeth’s cells for a short time, accused of stealing the share of the expedition’s plunder transported in Judith (Drake swore he had shared the loot among his crew when he thought them the sole survivors). Worse, Hawkins hinted that Drake had deliberately abandoned Minion—a taint of cowardice that infuriated Drake. It marked the last time he would sail as a pirate under another man’s flag.

This station in English society, Drake set about organizing his o clear his name, and to improve own expedition.

With two small ships, he ventured to Africa and the Caribbean in 1569. It is uncertain exactly who invested in this trip, though William Hawkins (patriarch of the pirate clan) may have contributed. Or perhaps Drake had indeed stolen the plunder of Judith. Drake termed the voyage a reconnaissance; certainly, he did not engage in piracy and avoided any trouble with a steadily increasing Spanish military presence in the region. Rather, he looked for weaknesses and allies. Apparently, the voyage proved profitable, as he purchased the 25-ton pinnace Swan after returning to Plymouth in 1570. That winter Drake returned to the Spanish Main as part of a three-ship fleet, and he returned as a pirate, intent on using the knowledge gained in his reconnaissance.

Drake anchored his largest ship near Cape Cativa on the Isthmus of Panama. From this relatively secure base, his pinnaces and barges ranged nearby waters. Allying with French corsairs operating in the region, he led a bold raid up the Chagres River to capture Spanish merchant shipping. When Spanish warships came to the rescue, Drake’s men, forced to abandon several prizes, took their small vessels into the shallow waters of secluded coves and creeks where the larger warships could not follow. Once the naval forces sailed for other problem areas, Drake and his men emerged to attack warehouses, towns and shipping. Finally, his ships packed to bursting, Drake cached supplies and extra valuables at his main base, which he named Port Pheasant, and sailed for home.

Despite the voyage’s undeniable success, Drake did not enter Plymouth Harbor until first confirming the queen did not consider him and his men pirates. Fortunately, the more than £100,000 in plunder managed to bring a blush to even a Virgin Queen’s cheeks— especially when Drake sent the pick of the jewelry her way. This raid made Drake famous, wealthy and a favorite of the queen, not to mention one of history’s most successful pirates.

Drake could have retired at this point (he did invest a share of his loot in land and shipping), but he had gleaned an idea from his attacks along the narrow Isthmus of Panama. Spain mined most of its silver and gold along the west coast of South America. Shipped to the isthmus, the treasure was transported by mule train east to the insignificant and poorly garrisoned port of Nombre de Dios, where it awaited the annual return of the great Spanish galleons. In May 1572, Drake loaded two vessels with 73 men, supplies and the small craft needed to operate along the coast. Over the following year, he hatched his plan to exploit the vulnerable mule trains.

Anchoring again at Port Pheasant, Drake readied his boats and men for a night assault on Nombre de Dios. The assault succeeded, though Drake collapsed from blood loss after taking a wound to the leg. Unfortunately, the Spanish fleet had just sailed with the treasure. A lesser pirate would have departed for England at this point, but Drake persevered. Through his pain, through Spanish pressure that forced him to abandon Port Pheasant for a new base, through a yellow-fever epidemic, even through the death of a brother later in the expedition, Drake remained committed to his goal. Finally, in April 1573, with help from cimarrones and a fellow pirate band, his surviving men attacked a Spanish mule train—though in a fighting retreat, the men abandoned much of the gold and their wounded. In August 1573, Drake’s force returned to Plymouth with its plunder and several prizes. He had lost more than half of those who had sailed with him, but the survivors were rich beyond their wildest dreams. As for Drake, he now topped Spain’s list of wanted Protestant pirates—a dead man if ever captured.

By then Francis Drake’s wealth exceeded that of many English nobles. His investments as a merchant always seemed to return dividends. People sought his council, even at court itself, where he appeared in company with the queen. In 1575 he served Elizabeth as an admiral in another of the seemingly unending expeditions against Irish rebels (as an indicator of his wealth, he personally provided three warships for the expedition). Yet Drake remained dissatisfied. As he was still a commoner, the nobility had no time for him, and many resented his wealth—after all, even a richly successful pirate still smells much like a common thief. Anyway, while looting ore-rich Catholics on the Isthmus of Panama, Drake had glimpsed something even more alluring—the Pacific, a sea that also carried Spanish treasure, and a sea where, at least in the Americas, Spain felt it had no enemies. In December1577, Drake managed to convince his Pirate Queen that the Spanish should be taught the error in their thinking.

Four ships and as many as 170 men accompanied Drake on his new quest for Spanish plunder. By the time the expedition had pillaged its way through the Cape Verde Islands, executed one of its own captains on the South American coast (eliminated as a threat to Drake’s authority), forced a passage of the Straits of Magellan and endured a violent Pacific storm shortly after exiting the straits, only one ship, Drake’s Pelican (which he had renamed Golden Hind) and 80 men remained. Suffering from scurvy, the English landed on the South American coast to gather fruits and vegetables. Hostile natives attacked the men, killing and wounding several, including Drake, who suffered arrow wounds to his face. His men muttered at the hardship and lack of tangible rewards.

Finally, in December 1578, Drake struck his Catholic targets, plundering the unprepared port of Valparaiso (in modern-day Chile) and capturing La Capitano, a fully laden merchantman anchored in its harbor. The wealth taken in this strike alone paid for the entire voyage, inspiring captain and suddenly loyal crew to further exploits in the face of a now alert Spanish military. From January to mid-April 1579, Drake terrorized King Philip’s South American possessions. Absent previous threats, these reaches had not been militarized to the level of the West Indies. They paid a heavy price in dead priests, burned churches and lost treasure. Here, Drake earned his sobriquet, El Draque—the dragon, come with flame and sword to slay Catholics and plunder settlements.

On March 1, Drake encountered the galleon Nuestra Señora de la Concepción, a target near and dear to his piratical heart. Known to her crew by the far more colorful name Cacafuego, the vessel was loaded to its gunwales with silver, gold and jewels. Disguised as a Spanish merchantman, Golden Hind crept closer, at last unleashing a crippling blast from its cannon. As yards and masts collapsed, Drake led his boarders into action, quickly quelling Spanish resistance. The next day, Drake split a portion of the silver and gold among his men, buying their everlasting loyalty. He could afford to, as Nuestra Señora de la Concepción was the richest single ship captured by an Englishman to that date.

In April, Drake abandoned the Spanish coast and sailed north to a quiet bay—most probably in modern-day California—to repair his worn Golden Hind. Then, rather than face gathering Spanish forces along the American coast, he sailed west. On Sept. 26, 1580, Drake and his 57 surviving crewmen arrived off Plymouth, erasing the boast that only a Spaniard had circumnavigated the world. Later that day, Golden Hind and an estimated £25 million rode peacefully at anchor in the harbor. Some weeks later, on the deck Drake had strode daily—and so successfully—for so many years, the Pirate Queen dubbed her most successful corsair “Sir Francis.”

Thus ends the story of Francis Drake the pirate and begins the story of Sir Francis Drake the English admiral. When Drake next led an expedition, it was as a military officer serving Queen Elizabeth (though plundering, treasure ships and the like still figured prominently here and there). Across five such expeditions, ranging from one of history’s greatest raids at Cádiz in 1587 to an absolute debacle at Lisbon in 1589, Drake met mixed results as a military commander—often because his piratical tendencies betrayed him.

Living in a time that justified piracy through religious hatred and in a state that depended on piracy to outlast a stronger enemy, Francis Drake prospered as a corsair. Moreover, the wealth he poured into Elizabeth’s treasury enabled her resistance against Spain (and drained even more wealth from the coffers of Philip II as he sought to guard against Drake and his ilk). Although the upper crust of English society never accepted Drake as an equal, the commoners loved him and turned him into a mythic hero, ever willing to rally his countrymen against the perfidious Spaniard. What other pirate in history can make that claim?

 

For further reading, Wade G. Dudley recommends his own Drake: For God, Queen and Plunder, and The Wind Commands Me: A Life of Sir Francis Drake, by Ernle Bradford.

Originally published in the July 2009 issue of Military History. To subscribe, click here

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