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.
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.
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.
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.
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.
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.
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.
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.
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