A Tale of Two Elizabeths: Two Queens Who Rewrote History
A Tale of Two Elizabeths: Two Queens Who Rewrote History

A Tale of Two Elizabeths: Two Queens Who Rewrote History

Khalid Elhassan - September 15, 2022

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Sir Francis Drake, by Jodocus Hondius. Diario da Historia

The Pirate Who Became a Favorite of Queen Elizabeth I

Sir Francis Drake (circa 1540 – 1596) was many things: a sea captain, naval officer, explorer, politician, slave trader, and privateer. At times, he was also an outright pirate. And not just any pirate, but Queen Elizabeth I’s favorite pirate. He gained her favor for good reason. The Virgin Queen invested in English pirates like modern venture capitalists invest in Silicon Valley startups, and she made out like a bandit from the returns on Drake’s high seas hijinks and predations.

Drake was the most celebrated seaman of the Elizabethan Era, and led one of history’s more adventurous careers. He first went to sea at an early age. As a teenager, he joined his relatives, the Hawkinses, a clan of privateers who preyed upon French coastal ships. By the 1560s, Drake had risen to command his own ship, entered the slave trade, and smuggled shackled captives illegally into Spain’s New World possession. By the time his storied career and life came to an end, Drake had become the greatest pirate of his day.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Queen Elizabeth I. Pinterest

Queen Elizabeth I Legalized Piracy

The fame – or infamy – of Francis Drake as a pirate is based on his track record of predation upon Spanish sea trade and coastal settlements. Much of it was driven by a desire for payback worthy of a Hollywood action adventure flick. In one of his early voyages, Drake was cornered by Spanish authorities, and escaped only with heavy loss of life among his crew. The experience left him with a lifelong hatred of Spain. In 1572, he received a Letter of Marque from Elizabeth I, that authorized him to plunder Spanish property.

Letters of marque were basically piracy licenses issued by governments. They allowed the bearers to prey upon and seize enemy ships. They could keep most of the proceeds, with a proviso that part of the profits from each seized ship belonged to the government that had issued the letter of marque. Armed with that authorization, Drake raided Panama, but was wounded and forced to retreat. After he recovered, he raided Spanish settlements around the Caribbean, and returned to England in 1573 with a rich haul of gold and silver.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
John Hawkins, the English slave trade pioneer in whose ventures Queen Elizabeth I invested. Wikimedia

The Virgin Queen Was Into Slavery as Well as Piracy

Piracy wasn’t the only dubious activity that Elizabeth I was into. She was also into slavery, indeed, she was one of the key early players who helped jump start the trans-Atlantic slave trade that saw tens of millions of shackled Africans shipped over to the New World. British involvement in the slave trade began in the sixteenth century. John Hawkins, a pioneering English naval commander, administrator, and privateer, became an early promoter of the slave trade. Indeed, he is the first known Englishman to have included African slaves in his cargo. Queen Elizabeth approved of the trade venture, and invested in it. Hawkins became the first Englishman to profit from the Triangle Trade. English goods were traded for slaves in Africa; slaves were shipped across the Atlantic and traded for New World goods; New World goods were shipped to England, and traded for English goods.

In 1562, Hawkins transported 300 slaves to the New World. He exchanged them for sugar, ginger, and hides, with which he returned to England. Elizabeth I got a cut of the profits, and for Hawkins’ next slave trade voyage, she contributed a ship by way of investment. She continued to profit from slave trade ventures for the rest of her reign. In the meantime, more and more Africans arrived in England, and became a noticeable presence. The queen did not mind the profit from Africans, and even employed some African entertainers in her court. However, the noticeable presence of Africans in England bothered her, and in 1596 she issued a decree to expel Africans from her realm.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
A replica of Francis Drake’s Golden Hind. Wikimedia

Piracy Enriched Elizabeth I

Sir Francis Drake was more than just a highly successful pirate. Queen Elizabeth I’s favorite sailor also became the second man to circumnavigate the globe after Ferdinand Magellan’s expedition. However, scratch the surface of any of Drake’s occupations, and piracy lurked beneath. True to character, he combined his voyage of exploration with opportunistic plunder of the Spanish. In 1577, he led an expedition of five ships to raid the Pacific coast of Spanish South America, which was wholly undefended in those days.

Drake braved massive storms, and passed through the Straits of Magellan in his flagship, the Golden Hind. He then sailed up the coasts of Chile and Peru, and near Lima, captured a Spanish ship that yielded 25,000 gold coins. Soon thereafter, he seized a fabulously rich prize, the Cacafuego, a Manila galleon that yielded a treasure of eighty pounds of gold, thirteen chests of coins, and twenty six tons of silver. Queen Elizabeth made out quite well from that prize. Both as an investor in Drake’s voyage, and as the sovereign who had issued him a permit to privateer, and to which a portion of the loot was owed.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Francis Drake’s circumnavigation of the world. Highbrow

Drake’s Exploits Cemented His Place as a Favorite of the Queen

His holds full of loot, Francis Drake crossed the Pacific, sailed the Indian Ocean, rounded the tip of Africa, and returned to England on September 26th, 1580. He had circumnavigated the globe. It was a first for a pirate, and the first time that anybody had accomplished that feat after Ferdinand Magellan’s expedition, over half a century earlier. Queen Elizabeth I’s favorite pirate was personally knighted by her aboard his ship, the Golden Hind, in 1581. He was also appointed mayor of Plymouth, England’s most important naval base.

In 1585, he was put in charge of a fleet that harried Spanish trade, captured Santiago in the Cape Verde Islands, and plundered Spanish settlements in Florida and Hispaniola. In 1587, as Spain’s King Philip II threatened war, Drake led preemptive raids against Spanish fleets that had begun to assemble in Cadiz and Coruna for an invasion of England. He inflicted significant damage, which prevented the Spaniards from sailing that year. As contemporaries described it, Drake had “Singed the King of Spain’s Beard“. He further cemented his place in history – and in the esteem of the queen -when he played a prominent role in the defeat of the 1588 Spanish Armada.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Queen Elizabeth I knights Francis Drake aboard his ship, the Golden Hind. Dissolve

An Elizabethan Adventurer’s End

Sir Francis Drake’s preemptive raids in 1587 delayed King Philip II’s plans to invade England, but did not scotch them for good. A year later, the combined Spanish fleet, the famous Armada, set sail. Drake played a key role in its dispersal and eventual destruction. Particularly on the night of July 29th, 1588, when he organized fire ships against the Armada assembled in Calais. In a panic, the Spanish ships sailed out of that port and into the open sea. There, they were scattered by a combination of English warships and bad weather. It was the peak of Drake’s success, as well as his popularity both with the public and in the royal court. From then on, things were mostly anticlimactic, until his eventful life eventually came to an anticlimactic end in 1596.

After a series of failed raids and attacks against Spanish America, Drake caught dysentery while anchored off Portobelo in Panama, and died. His career, with its turns from soldier and sailor to pirate, illustrates the era’s murky lines between outright piracy and legalized piracy, also known as privateering. In the years to come, the difference between a pirate liable for the hangman’s noose, and a privateer likely to receive official acclaim and adulation, was no more than a piece of paper. Those who plundered the seas with a letter of marque in their pocket were lionized. Those who did the same without such a fig of legality were condemned as pirates.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
The Cornwall coast. The Cornwall Guide

Elizabeth I Was Pretty Soft on Pirates

As seen above, the fondness of Queen Elizabeth I for Francis Drake was indicative of a soft spot for pirates and piracy – at least of the legalized kind. Another example of her softness on pirates – of the outright illegal kind – can be seen in how the Virgin Queen dealt with female pirate Lady Killigrew. A strong, fearless, and independent woman, Mary (sometimes Elizabeth) Wolverston, better known to history as Lady Killigrew (circa 1525 – circa 1587), was an English gentlewoman from Suffolk who led a double life as a pirate. She was accused and convicted of organizing a piracy ring that preyed on English ships that passed through the coastal waters of Cornwall.

The rocky coast of Cornwall, where Killigrew carried out her piratical activities, had long been a home to smugglers, wreckers, and pirates. Piracy was in Mary’s blood, as her father, Phillip Wolverton, Lord of Wolverton Hall, had been a gentleman pirate for years. It was an era when piracy was almost an English pastime, often abetted or outright encouraged by the authorities. Particularly in the wars against Catholic Spain, when the line between English pirates and the English navy was often indistinguishable.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Replica of a Spanish ship of the 1500s. Pinterest

The Downfall of a Female Pirate

Mary Wolverston was married and widowed at a young age. She then remarried, this time to Sir John IV Killigrew, and became Lady Killigrew. Her second husband, like her father, had also been a pirate. However, unlike her father, who had retired from piracy, Mary’s second husband was still an active pirate. In of itself, that was not too problematic. Elizabeth I and her officials encouraged piracy on the high seas, as a form of economic warfare against the country’s enemies. So long as it was conducted far away and in a manner that allowed the English government some measure of plausible deniability, it was not much of a problem.

Unfortunately, Lady Killigrew and her husband did not prey solely upon enemy ships in the high seas, but also engaged in piracy in English waters, against foreign and English ships. Lady Killigrew’s downfall came in early 1583, when a Spanish ship, Marie of San Sebastian, docked at Arwenack near her castle. When she learned that the ship carried treasure, Lady Killigrew entertained the captain and crew at her castle, and had them visit her estates inland. While her guests were absent from their ship, Lady Killigrew led a raid that seized the Spanish ship, killed all who resisted, and absconded with the cargo.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Elizabeth I accepted bribes to let Lady Killigrew off the hook. Luminarium

Elizabeth I Accepted Bribes to Let This Pirate Off the Hook

When the captain and crew of the Marie of San Sebastian returned to Arwenack and discovered what had happened, they complained to the local authorities. The local judge, however, was Lady Killigrew’s son, so their complaint went nowhere. Enraged, the Spaniards journeyed on to London, where they enlisted the Spanish ambassador’s help. Lady Killigrew’s latest piratical foray was not the kind of discrete piracy carried out far away, but a brazen act of piracy carried out in English waters. It threatened to cause a diplomatic crisis.

The authorities in London were forced to act, and they sent officials to take a look. When it was discovered that Lady Killigrew’s son, the judge, had tampered with the local investigation, she and her chief accomplices were arrested. Some of the stolen goods from the Marie of San Sebastian were discovered in her house, so receiving and fencing stolen goods was added to her charges. She was tried, convicted, and sentenced to death. Two of her accomplices were executed, but she received a commutation from Queen Elizabeth, and was later released from prison after her son doled out lavish bribes.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
A violent death in medieval Ireland. Irish Archaeology

The Most Famous Female Pirate of the Elizabethan Age

Grace O’Malley (circa 1530 – circa 1603) was a sixteenth century Irish heroine. She fought the English in the reign of Elizabeth I on land, and preyed upon their ships at sea. Her English foes vilified her as “a woman who hath imprudently passed the part of womanhood“, and she was mostly ignored by contemporary chroniclers. Yet, her memory lived on in native folklore, and nationalists later lionized her as an icon of the Irish fight for freedom and struggle against foreign domination.

There were two Irelands back in those days, with two distinct cultures. On the one hand, there was Dublin and its surrounding counties, an English enclave ever fearful of the hinterland that comprised the rest of Ireland. That rest of Ireland was the land of the native Irish and the Gaelicized Old English. The English viewed them as uncivilized and wild, given to raid and strife and interminable violence. Grace O’Malley was born and raised in Connaught, in western Ireland, and belonged to that “wild Irish” hinterland, which consisted of numerous autonomous territories.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Grace O’Malley. Wikimedia

The Start of a Piratical Career

The rulers and inhabitants of Connaught frequently feuded, raided each other, rustled cattle, captured and lost castles and strongholds, and otherwise vied for advantage and dominance. All were part of a clientele system, in which the weak aligned with the strong, and offered tribute in exchange for protection. The O’Malleys were Irish nobility with clients of their own, who looked to them for protection. They were, in turn, clients of another, even more powerful family. They traded produce and raw materials for luxury good, fished, ferried passengers, levied tolls on ships that passed through their waters, and engaged in opportunistic piracy.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Clare Island. Galway Tourism

For protection, the O’Malleys built a row of castles along the coast. Grace was born in that environment, married in 1546, and bore three children before her husband was killed in an ambush in 1565. Because of the era’s misogynistic laws, she was unable to inherit her husband’s property. So she settled on Clare Island, and made it her stronghold and base of operations. O’Malley started off with three galleys and a number of smaller boats. She commenced her career in piracy with attacks on ships that plied the region’s waters, and raids against coastal targets.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Rockfleet Castle, one of Grace O’Malley’s strongholds. YouTube

The Elizabethan Era’s “Dark Lady of Doona”

Grace O’Malley seethed over the laws that deprived her of her husband’s property, as she built up her pirate fleet. In the meantime, she consoled herself with a shipwrecked sailor, who became her lover. When he was killed by a rival family, the MacMahons, history got its first glimpse of O’Malley’s ferocity. To avenge her beau, she attacked Doona castle, where her lover’s murderers were holed up, and killed them. That earned her the nickname: “Dark Lady of Doona. She remarried in 1566, but still mad at her sailor lover’s murder, she had another go at the MacMahons in Doona Castle. She seized it in a surprise attack, while the garrison was busy with prayers.

Around that time, O’Malley also went after a thief who stole from her, then fled to a church for sanctuary. She surrounded the church and decided to wait him out, as she taunted him that his only choices were starvation of surrender. He chose a third option, dug a tunnel, and escaped. O’Malley became Ireland’s sea mistress, and a pirate queen who controlled the waters around Connaught with an iron fist. She preyed on sea traffic and coastal communities along Ireland’s western coast, as well as on eastern settlements on the Irish Sea.

A Tale of Two Elizabeths: Two Queens Who Rewrote History
Grace O’Malley and Queen Elizabeth I. Pinterest

When a Pirate Queen Met Queen Elizabeth I

While she expanded her control and power, Grace O’Malley personally led a raid on a seaside stronghold known as Cocks Castle. She captured it, and to commemorate her courage, it became known thereafter as Hens Castle. Unfortunately for O’Malley, things soon took a turn for the worse. After they defeated the Spanish Armada in 1588, the English were able to focus on the consolidation of their grip on Ireland, and the fight against Irish piracy and pirates such as O’Malley. To resist that English expansion, O’Malley allied with Irish lords who had risen in revolt against the English. However, in 1593, the English captured her sons and brother.

So O’Malley sailed to England, to personally petition Queen Elizabeth I for their release. She met the English queen at Greenwich Castle. There, O’Malley reportedly refused to bow, on the grounds that she did not recognize Elizabeth as Queen of Ireland. Elizabeth extracted O’Malley a promise to cease her assistance to Irish rebels. Elizabeth did not live up to her part of the bargain, however, so Grace O’Malley went back to helping the rebels, and reportedly died in one of her castles in 1603.


Where Did We Find This Stuff? Some Sources and Further Reading

Ancient Origins – Grace O’Malley: The 16th Century Pirate Queen of Ireland

Bond, Jennie – Elizabeth: 80 Glorious Years (2006)

Botting, Douglas – The Pirates (1978)

Economist, The, April 7th, 2018 – Muslims Consider Queen Elizabeth’s Ties to the Prophet Muhammad

Elizabethan Era Org – Teenage Scandal of Queen Elizabeth I

Encyclopedia Britannica – Thomas Seymour, Baron Seymour

Guardian, The, June 2nd, 2021 – Buckingham Palace Banned Ethnic Minorities from Office Roles

Hibbert, Christopher – The Virgin Queen: Elizabeth I, Genius of the Golden Age (1992)

History – Is Queen Elizabeth Related to the Prophet Muhammad?

History Collection – 40 Violent Realities in the Making of the British Empire

History Extra – Did Thomas Seymour Sexually Abuse the Teenage Princess Elizabeth?

History Ireland, March/ April 2005, Volume 13 – Grainne Mhaol, Pirate Queen of Connacht: Behind the Legend

History Jar – Elizabeth and Thomas Seymour

History Jar – Scandal at Chelsea: the Courtship and Marriage of Katherine Parr and Sir Thomas Seymour

Insider – Here’s Where the Royal Family Gets Their Money

Jenkins, Elizabeth – Elizabeth the Great (1959)

Kelsey, Harry – Sir Francis Drake, the Queen’s Pirate (1998)

Lane, Kris E. – Pillaging the Empire: Piracy in the Americas, 1500-1750 (1998)

National WWII Museum – A Princess at War: Queen Elizabeth II During World War II

New York Times, July 22nd, 1982 – Text of Scotland Yard’s Report on July 9 Intrusion Into Buckingham Palace

Pirate Empire – Lady Pirate, Mary/ Elizabeth Killigrew

Sharp, Anne Wallace – Daring Pirate Women (2002)

Times, The, April 12th, 2018 – The Queen May Be a Child of the Prophet Muhammad

UK National Portrait Gallery – The Slave Trade

Vanity Fair, June 1st, 2016 – See Rare Footage of Queen Elizabeth II Meeting Marilyn Monroe