Sir Walter Raleigh was an Intriguing Man in History

Sir Walter Raleigh was an Intriguing Man in History

Larry Holzwarth - July 12, 2019

The organizer and champion of England’s first attempt to establish a colony in the New World, Sir Walter Raleigh was a polymath of the Elizabethan Age. He was a sailor and explorer, a courtier, and a writer of history, philosopher, and poet who achieved near-mythic status after his death. Considered to have been the epitome of gentlemanly behavior and chivalry, Raleigh is the subject of a legend which describes him spreading his cloak over a mud puddle so that Her Majesty’s shoes and skirts would not be soiled. He was also a spy for Her Majesty Queen Elizabeth, and accused of conspiring against her as well. A man of mystery and myth, here are forty facts about Sir Walter Raleigh, polymath and adventurer.

Sir Walter Raleigh was an Intriguing Man in History
Sir Walter Raleigh was an adventurer who served as both a soldier and a seaman for England. Wikimedia

1. He fought for French Protestants persecuted by their King

Raleigh was born into a family which was perpetually short of hard money, but which had a distinguished reputation in the West Country of England. Officially he attended Oxford (Oriel College) but during the time period of which he was supposed to be in attendance at school he was in France, fighting as a soldier of fortune against the Catholic persecution of the Huguenots. His actions in France gained him an enviable reputation as a soldier and adventurer, as well as heroic status among Protestants during a time of religious wars throughout Europe. In the early 1570s he returned to England, where he learned the law at the Inns of Court in London. He also gained note as a writer of romantic poetry.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh lived in this house at Blackwall in London, one of many residences he occupied during his lifetime. National Maritime Museum (UK)

2. His half-brother attempted to colonize North America

Raleigh was half-brother to Sir Humphrey Gilbert, who in 1578 held a royal patent to establish colonies in North America, a process then dominated by the Spanish and to a lesser but growing extent the French. Gilbert used the patent as an excuse to raid Spanish settlements and ships, and convinced the young Raleigh to accompany him on a voyage which promised adventure and wealth. Although the journey was hazardous, delivering on the adventure part of the promise, the wealth did not materialize. The sight of the lands of North America instilled in Raleigh as desire to establish colonies, as a means of acquiring landed estates of his own, which became a life-long ambition.

Sir Walter Raleigh was an Intriguing Man in History
A portrait of Elizabeth I by an unknown artist, believed to have been done in the 1570s. Wikimedia

3. Raleigh enhanced his reputation through brutal suppression in Ireland

In 1580, Raleigh joined, again as a gentleman-adventurer, an expedition to Ireland, then a colony of England. The Irish subjects in rebellion to the Queen found in Raleigh a brutal and brutally effective soldier. Raleigh was soon the de facto commander of the English expedition to end the rebellion, and his success was brought to the attention of the English Court of Queen Elizabeth I. Her Majesty summoned the adventurer to her presence, where his dashing manners and reputation rendered him an immediate favorite of the Virgin Queen, which created for him several enemies among the gentlemen present in her court, both from personal jealousy and from suspicion of Raleigh’s motives and goals.

Sir Walter Raleigh was an Intriguing Man in History
Elizabeth bestowed honors and awards on Raleigh, though he had many rivals for her attention in her court. Wikimedia

4. Raleigh became Sir Walter Raleigh through the good graces of the Queen

In gratitude for his suppressing the rebellion in Ireland, and as a means of checking the power of other courtiers who schemed against her and her ministers, Queen Elizabeth granted to Walter Raleigh landed estates in Ireland, along with Royal patents and licenses which allowed him to collect substantial sums from the Irish peasants who worked his lands, or operated as merchants or publicans. His financial status assured, Raleigh was also granted the title of Sir Walter when Elizabeth knighted him in 1585. Two years earlier, Gilbert Humphrey had died, having failed to establish an English colony in Newfoundland, and Raleigh lobbied Her Majesty for the license to colonize North America for the English.

Sir Walter Raleigh was an Intriguing Man in History
Even when nominally at peace with Spain, Elizabeth encouraged her captain’s to prey on the Spanish treasure fleets from the New World. Wikimedia

5. Raleigh wanted to establish colonies for the purpose of preying on the Spanish treasure fleets

When Walter Raleigh applied to his Sovereign Queen Elizabeth for the right to establish colonies in the New World, his eye was on the treasure being acquired by Spain. Raleigh envisioned English bases in the New World from which English ships could intercept the Spanish galleons, relieving them of the vast treasures which were enriching the Spanish Empire. As Elizabeth played a coy game with the monarchs of Europe, using the potential of marriage to her as a diplomatic foil, she entertained the idea of weakening Spain and France through the establishment of an overseas empire. Thus she was intrigued by Raleigh’s proposals, and approved of them, though quietly.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh’s failure to establish a permanent Virginia colony tarnished his reputation in court, and led to further misadventures. Wikimedia

6. The first Roanoke expedition

In 1584, before he became Sir Walter Raleigh, the adventurer obtained permission from Her Majesty to explore the North American coast for a suitable site of a permanent English settlement in North America. Raleigh, unwilling to leave London due to the intrigue which could damage his position during a long absence, dispatched an expedition tasked with examining the Outer Banks region of the Atlantic coastline, which from reports he believed to be an ideal location from which to launch raids against the Spanish. When he received favorable reports as a result of the expedition he arranged for a second voyage to North America, to establish a permanent colony, though for reasons similar to those earlier he declined to surrender his position in court by going himself.

Sir Walter Raleigh was an Intriguing Man in History
Sir Richard Grenville was Raleigh’s associate in the creation of a colony in North America. Wikimedia

7. The Second Roanoke expedition and the establishment of the colony

Raleigh relied on his cousin and confidant, Sir Richard Grenville, to establish a permanent colony on the islands off the coast of what is now North Carolina, in an area which he named Virginia in honor of Elizabeth, the Virgin Queen. The colonists established a settlement on the island of Roanoke. Established in 1585, problems with the natives led to a large number of colonists abandoning the settlement and returning to England the following year, carried home by Sir Francis Drake. A small retinue of settlers remained to maintain the colony. When Raleigh learned of the difficulties on the island he arranged for another expedition to the colony, led by John White, who had been designated as governor of the settlement.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh, Grenville, and other English adventurers often met in this Devon house for refreshment and to discuss future plans. Wikimedia

8. The Lost Colony and Raleigh’s faltering prestige

In July 1587, Governor White left the struggling settlement in North America and returned to England to request additional settlers and support for the colony. Before he could return the Anglo-Spanish War, which featured the great fleet known as the Spanish Armada, intervened. When White finally arrived at the colony site in 1590, all that remained of the settlement were dismantled houses and fortifications, and the cryptic word CROATOAN carved into a fence post, with a nearby tree bearing the letters CRO. A signal which had been previously instructed by White to be left behind should the colonists be forced to evacuate, that of a Maltese Cross carved into a tree, was not to be found. Raleigh’s colony had vanished, its fate never to be fully ascertained.

Sir Walter Raleigh was an Intriguing Man in History
An engraving of Raleigh enjoying a pipe, and being doused by a servant who believed his master was on fire. Wikimedia

9. Raleigh fell into disfavor with the Queen

Following the collapse of the colonization effort in North America, Raleigh secretly married Elizabeth Throckmorton, who held a position in court as one of the Queen’s ladies-in-waiting. Raleigh did not seek Her Majesty’s permission for the marriage. Elizabeth Throckmorton, known as Bess, was pregnant at her wedding, and gave birth to a son shortly after the marriage took place, though the boy died of plague within a year. Bess resumed her duties as a lady in waiting to the Queen, who discovered the marriage in 1592. In a rage, Elizabeth dismissed Bess and ordered her with her husband imprisoned in the Tower of London. Raleigh remained a prisoner in the Tower for approximately two months before being summoned before Her Majesty, who had need of his services yet again.

Sir Walter Raleigh was an Intriguing Man in History
Philip II of Spain, whose treasure fleets were harassed and raided by English captains on the high seas. Wikimedia

10. Raleigh divided the spoils captured by an English fleet

In August 1592, Raleigh was summoned to Elizabeth’s presence, where he was tasked with secretly supervising the division of spoils captured from the Spanish by an English raiding party. Elizabeth had recalled the raiding fleet, but before they received word of the Queen desiring them to return to England the fleet captured the Spanish ship Madre de Deus, and with it a vast treasure. Loath to return badly needed hard specie, Elizabeth sent Raleigh to divide the spoils in a manner which would be acceptable to the captains who had captured it and the Spanish who wanted it back. After he successfully arranged an agreement acceptable to all parties, Her Majesty returned Raleigh to the Tower, where he remained until the first months of 1593.

Sir Walter Raleigh was an Intriguing Man in History
A map of “Virginia” which shows a fairly accurate depiction of the Outer Banks of what is now North Carolina. Wikimedia

11. Raleigh was elected to Parliament in 1593

Although still in disfavor as regarded the Queen, Raleigh stood for and won election to Parliament in 1593, representing a district in Cornwall. An agreement with the Queen allowed him to leave the Tower and take up residence at his estate at Sherborne, which had been granted to him by Her Majesty as a reward for earlier services. Away from the court and the intrigues which surrounded the Queen, Raleigh established himself in the area as a gentleman of standing, although his often frankly stated views on the subject of religion were found offensive by some, and he was charged for a time with being an atheist, a serious crime in Elizabethan England, though the charges were eventually dropped. In Parliament Raleigh became an expert on naval affairs.

Sir Walter Raleigh was an Intriguing Man in History
An oval portrait of Sir Walter Raleigh, whose pursuit of the legend of El Dorado led to his eventual downfall. Wikimedia

12. Raleigh helped to create the legend of the City of Gold known as El Dorado

Sometime around 1594, Raleigh learned of the Spanish accounts of a city of gold in Central or South America. In response he outfitted an expedition which he accompanied to the New World in search of the fabled city, leading him to explore much of what is now Venezuela and Guyana. He published a fictionalized account of his journey in 1596, titled The Discovery of Guiana. In his work he documented the lost city of gold, and numerous vast gold mines in the region, all of which were evidently figments of his imagination. The book and voyage had the effect of establishing Raleigh as one of England’s greatest explorers and navigators, erasing from the public mind the failure of the colony in the New World.

Sir Walter Raleigh was an Intriguing Man in History
During the Anglo-Spanish Wars the English fleet was inferior – in numbers of ships – to that of the Spanish Empire. Wikimedia

13. The former soldier became a leading naval officer during the Anglo-Spanish Wars

Raleigh was wounded during the English expedition to capture the Spanish port of Cadiz in 1596, though he recovered in time to join the English expedition to the Azores the following year, known as the Islands Voyage. The joint Anglo-Dutch expedition was a failure for the allies, and Raleigh returned to England in time to be an active leader of the English defense against the Spanish Armada, officially the Third Spanish Armada. It was this Spanish Fleet that found itself defeated by the weather in the English Channel and off the Irish Coast as much as by the actions of the English ships, though the British Navy counts its first great heroes among the men who commanded English vessels, including Drake and Raleigh.

Sir Walter Raleigh was an Intriguing Man in History
Sir Walter Raliegh’s contemporary and fellow adventurer and seaman, Sir Francis Drake. Wikimedia

14. Queen Elizabeth considered Raleigh to be ungrateful and disloyal

Despite Raleigh’s many services to his monarch, Queen Elizabeth continued to hold the adventurer at arm’s length. In 1592 Elizabeth had granted several rewards to Sir Walter, including his Sherborne estate, Durham House, in London’s Strand, and honorary titles and sinecures, including the title of Captain of the Yeomanry of the Guard (whose members wore the uniforms now associated with the Beefeaters). Nonetheless, the circumstances of his marriage (which Elizabeth doubly resented since it seemed to be a happy one) and the whispers of his enemies in the court kept the Queen from being as open with Sir Walter as she had once been, a circumstance which worsened as Her Majesty experienced the indignities of aging.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh’s governership of Jersey was as much an exile from the Royal Court at a place of honor. Wikimedia

15. Raleigh served as the Governor of Jersey in the early 17th century

By 1601 Raleigh was a sitting Member of Parliament representing three different counties, a distinction which for the Elizabethan period he held alone. In addition, beginning in 1600 Sir Walter served as the governor of Jersey, one of the Channel Islands off the coast of France. He used his experience as a soldier and as a naval officer to build defenses for the island which made it all but impermeable to enemy attack, including what is known today as Elizabeth Castle. Elizabeth continued to contact him via messengers and envoys, but continued to deny his presence in her court, encouraged by courtiers who considered the adventurer to be self-serving and potentially dangerous.

Sir Walter Raleigh was an Intriguing Man in History
When James VI and I inherited the throne of England, he brought to it a distrust of Raleigh of long-standing. Wikimedia

16. Raleigh was restored to Her Majesty Queen Elizabeth’s good graces

By 1602 Sir Walter Raleigh was welcomed into the Queen’s court, her favors again bestowed upon him, for which he expressed his gratitude appropriately. On March 24, 1603, Queen Elizabeth I died, and with the rest of England, Raleigh and others considered to whom the throne would be bequeathed. The monarchy was to be assumed by James VI of Scotland, the nephew of the late Queen, who would rule as James VI of Scotland and James I of England. A band of courtiers who opposed the ascendancy of James to the throne of England plotted to remove him and award the crown to Arbella Stuart. The conspirators were allegedly funded by agents of the Spanish King, who traveled between the kingdoms via the island of Jersey, where Raleigh held power and allegedly abetted them.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh’s support of Elizabeth against her half-sister, Mary (left) created suspicion about him in the mind of Mary’s son, James (right). Wikimedia

17. Raleigh was charged with treason for his alleged role in the “Main Plot”

Whether or not there actually was a conspiracy to deny the throne to James VI and I which became known as the “Main Plot” has never been determined to a certainty by historians. James was the son of Mary, half-sister to the late Queen Elizabeth, who had been tried and executed by the English monarch. James had long entertained resentments against those who had been loyal to Elizabeth at the expense of Mary, including Walter Raleigh and other named members of the Main Plot. In the summer of 1603 Raleigh and other conspirators were charged by the king with treason, for conspiring with the Spanish to overthrow the throne and establish a Stuart line of succession through Lady Arbella Stuart. Raleigh was arrested and brought to London for trial.

Sir Walter Raleigh was an Intriguing Man in History
A confession written and signed by Henry Brooke, Baron Cobham, was the sole evidence against Raleigh at his trial. Wikimedia

18. Raleigh served as his own attorney at his trial for treason

Sir Walter Raleigh was tried beginning in November, 1603. The main evidence against him was a signed confession from Baron Cobham, Henry Brooke, one of the conspirators who had given state’s evidence. Raleigh was allowed to dispute the confession, but not to call Cobham to the stand to testify before the court. Raleigh based his defense on the “confession” being little more than hearsay, but despite his repeated demands to be able to confront his chief accuser in the presence of the jury, he was denied that basic legal right. Raleigh denied all knowledge of the plot and a conspiracy against the king, but the jury convicted him and he was sentenced to death, remanded to the Tower to await his execution.

Sir Walter Raleigh was an Intriguing Man in History
Imprisoned in the Tower, Raleigh occupied his time writing history, philosophy, and poetry. Wikimedia

19. Imprisoned for more than a decade, Raleigh took to writing

Sir Walter Raleigh was sent to the Tower under a sentence of death, but James VI and I was hesitant to allow the execution of a man who was so well regarded throughout his realm. There was also the perceived threat that the execution of a man aligned with Spain could lead to further armed conflicts with the Spanish Empire. Raleigh remained a prisoner in the Tower for over a decade, during which time he resided in comparatively luxurious apartments rather than in the dungeons which the image of the Tower of London brings to mind. He occupied his time by writing religious and political tracts, poetry, and a monumental work which he called The Historie of the World, an historical piece which argued against the divine rights of kings and monarchical governments in general.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh continued to annoy his sovereign, James VI and I, with his writings, but the King refused to order his sentence of execution carried out. Wikimedia

20. With a death sentence over his head, Raleigh continued to exasperate the king

Raleigh’s Historie of the World did not concentrate on recent history in Western Europe, but instead focused on the ancient worlds of the Greeks, Mesopotamians, Phoenicians, Romans, and other civilizations. He concentrated on geography, and how the expansion of realms was often dictated by geographical features. In his work he often couched his words over government and rulers in terms meant to serve as advice to the current monarch on the throne of England, who did not receive them well. James considered Raleigh’s perceived advice to be overly critical, especially as they came from a mere commoner, who had through good fortune and the beneficence of his monarch achieved fame and success.

Sir Walter Raleigh was an Intriguing Man in History
As a poet Raleigh’s works rivalled those of Edmund Spenser, in both critical and public acclaim. Wikimedia

21. Raleigh also wrote popular poetry during his imprisonment in the Tower

Besides tweaking the sensibilities of King James VI and I while he was His Majesty’s prisoner, Raleigh wrote poetry while in residence in the Tower. Much of Raleigh’s poetry was of a personal nature, reflecting the experiences of his own lifetime and the resultant senses of loss, of love, and of the passage of time. Some were short ditties, others long poems of a classical nature a la Edmund Spenser or John Donne, both of whom were his contemporaries, though neither enjoyed his fame during their lifetimes. Some of Raleigh’s poetry served to keep his accomplishments, many of which he exaggerated, in the public eye as he squandered his time in the tower.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh’s family resided with him in the Tower during his imprisonment, a normal circumstance for the time. Wikimedia

22. His family resided in the Tower with him

Sir Walter Raleigh was accompanied by his family during most of his stay in the Tower of London, as well as by servants which saw to his needs, did his laundry, prepared and served his food, and catered to his whims. The enterprising Raleigh was well aware of an underground network in London through which servants cared for their charges while exchanging gossip, and through the network (as well as in some of his poetry) word began to be bandied about regarding his awareness of the location of rich veins of gold and silver in the lands he had explored previously in Guiana and Venezuela. Raleigh, through subterfuge, lobbied the king and his ministers to allow another expedition to recover the great wealth of which only he knew for certain, for the benefit of the king and his kingdom.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh continued to promote a voyage to Guyana in pursuit of gold while imprisoned in the Tower. Wikimedia

23. Raleigh attempted to persuade the king through convincing the public

Raleigh contributed significantly to the myth of the lost city of gold known as El Dorado, and through his writings and in particular his poetry he kept the idea alive of vast wealth available for the taking. After several years of living in the Tower, the adventurer contacted the king directly and through his ministers, with proposals for an expedition to South America and the recovery of gold not already in the hands of the Spanish or Portuguese. War with Spain was a consideration for the British King, especially after the establishment of the permanent settlement at Jamestown in Virginia, and at Bermuda. English settlements were vulnerable to Spanish ships, and peace with Spain was by then essential to the expanding English colonial empire.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh’s reports of gold in Guiana led to another expedition despite the potential of trouble with Spain. Wikimedia

24. Raleigh proposes another Guiana expedition

By the second decade of the 17th century Sir Walter Raleigh presented to King James VI and I a plan through which an English expedition, led by Raleigh, would explore the Guiana region he had previously visited, and establish a presence there which would be supported by the colonies on the islands and on the North American continent. The chief concerns of the English monarch were the reaction of the Spanish and Portuguese, and as part of the charter authorizing Raleigh’s expedition it was made clear that no threat to any Spanish activity or settlement would be tolerated, nor were hostile defensive operations to be allowed. The expedition was to treat itself as guests of the Spanish rather than rivals, probably an unreasonable expectation, but one which Raleigh agreed to honor.

Sir Walter Raleigh was an Intriguing Man in History
Though Raleigh received a partial pardon from James VI and I it contained a caveat which led to his downfall. Wikimedia

25. Raleigh was pardoned and released from the Tower in 1617

In 1617 King James VI and I succumbed to the public fervor over the existence of the lost city of gold known as El Dorado, and issued a Royal Pardon for Sir Walter Raleigh. During his long imprisonment Raleigh, in addition to fathering a son, Carew Raleigh, had created much of the fervor over the gold. In addition to the pardon, James granted the adventurer permission to return to Guiana in command of an expedition tasked with finding the mythical city which was largely the creation of Raleigh’s own mind. At the time England and Spain were enjoying a period of relative peace, although English sea raiders continued to prey surreptitiously on Spanish treasure ships.

Sir Walter Raleigh was an Intriguing Man in History
In his writings to generate public enthusiasm for an expedition to Guiana, Raleigh described the “headless” tribesmen encountered there. Wikimedia

26. The Second Guiana Expedition lead to conflict with Spanish settlements

During Raleigh’s first expedition to Guiana he was accompanied by a fellow seaman and longtime friend, Lawrence Keymis (also spelled Kemys). Keymis had been imprisoned for a time in the Tower with Raleigh, though he was released at the end of 1603, and afterwards served Sir Walter as his literary agent while the latter remained in the Tower. Keymis had made a second voyage to Guiana following his first with Raleigh in the 1590s, and related to Sir Walter his certain knowledge of a rich vein of gold unknown to the Spanish near the Orinoco River. When Raleigh obtained the Royal permission to return to Guiana, Keymis joined the expedition as a pilot. It was Raleigh’s second voyage to Guiana, Keymis’s third.

Sir Walter Raleigh was an Intriguing Man in History
The power of the Spanish Empire led to Raleigh receiving strict orders not to enter into conflict with their settlements or ships. Wikimedia

27. Raleigh’s elder son Walter accompanied the expedition as well

The expedition which departed England in 1617 carried both Raleigh and Keymis, and Sir Walter’s son and namesake as well. They were under strict orders not to hamper or harass the Spanish in any manner, orders which Sir Walter reinforced with orders of his own upon arrival at the Orinoco River. While exploring the Orinoco River, a party of men under the command of Keymis and including the younger Walter Raleigh encountered a Spanish outpost known as Santo Tome de Guayana. Whether the English party attacked the Spanish or responded to Spanish aggression has been disputed down the centuries, but a hostile encounter took place there, and the younger Raleigh was the first man killed, according to English accounts.

Sir Walter Raleigh was an Intriguing Man in History
Frontispiece for Raleigh’s book describing Guiana and the wealth to be taken there. Wikimedia

28. Santo Tome de Guayana

The encounter between the English party under Keymis and the Spanish settlement of Santo Tome was a minor affair, with two Englishmen and two Spaniards killed by musket fire, before the smaller Spanish garrison of the settlement fled. Keymis held the town for the ensuing 29 days, sending out small search parties in pursuit of the promised vein of ore he had claimed to have knowledge of, but no gold was found. Surrounded by hostile Spanish troops, Keymis had his men loot the settlement before torching it, and fled downriver in ship’s boats, where he rendezvoused with Raleigh on March 2, 1618. Keymis had previously reported the battle and the death of Raleigh’s son by letter, upon his return to the fleet he found Raleigh despondent and resentful.

Sir Walter Raleigh was an Intriguing Man in History
A map of the region where Raleigh believed unlimited gold was to be had in Guiana, where Spanish settlements were already present. Wikimedia

29. Keymis committed suicide rather than return to face the wrath of the King

When Keymis encountered Sir Walter Raleigh upon returning to the fleet in the mouth of the Orinoco he found the latter unwilling to offer any support to his former friend. “I told him he had undone me by his obstinacy” Raleigh later wrote. When Keymis realized that he had placed Raleigh under a renewed sentence of death for having violated the conditions of his pardon, he first attempted suicide by shooting himself in the chest with a pistol. When the wound did not prove immediately fatal, Keymis plunged a knife into his chest, penetrating the heart, and killing him.

Sir Walter Raleigh was an Intriguing Man in History
Although Raleigh was a highly regarded hero among the populace, political enemies branded him as guilty of high treason upon his return to England. Colonial Williamsburg

30. Raleigh returned to England knowing what his fate would be

When Raleigh returned with the failed expedition to Plymouth, he learned of a movement afoot under the impetus of the Spanish Ambassador to have him brought before the King and his death sentence reinstated. Under the threats of Spanish retaliation, James VI and I had little available in the way of options, war with Spain was at the time unthinkable, and Raleigh had failed to enrich the Royal coffers with gold and silver from El Dorado. Raleigh was ordered to be brought from the anchorage at Plymouth to London, under escort provided by Sir Lewis Stukley, who was ordered by the King to not keep too close a watch upon his charge, affording Sir Walter the chance to escape.

Sir Walter Raleigh was an Intriguing Man in History
King James gave orders to move Raleigh to London slowly in the hope the adventurer would escape to self-imposed exile. National Library of Scotland

31. Raleigh attempted to escape from Stukley on at least one occasion

Stukley was given orders, from the King, to not use too much haste in bringing the prisoner to London, which Stukley – a long-time enemy of Raleigh’s – understood to mean he was to be solicitous of his prisoner’s health, rather than lax on his guard. Nonetheless Raleigh did escape, eluding his captors for a brief time as he sought a means to flee to France, but after the cargo of tobacco carried on his ship back from the Orinoco was sold off in his absence, Sir Walter lacked the funds to flee successfully. He returned voluntarily to custody. During the journey to London Raleigh tried to bribe his captor, using funds offered for the purpose by friends, and connived with friendly doctors to feign illnesses which slowed the journey.

Sir Walter Raleigh was an Intriguing Man in History
With Raleigh again incarcerated in the Tower, his political enemies and Spanish emissaries clamored for his execution. Wikimedia

32. Stukley double-crossed Raleigh in London

Raleigh and his party, including Stukley, were in London by the first week of August, and Raleigh unveiled a plan by which he would escape down the Thames on August 9, which included Stukley as a willing participant in the plan. Stukley, however, had joined the plot with the intent of allowing Raleigh to get away temporarily, demonstrating his intention to flee to a French ship, and thus further treason against His Majesty. Once Raleigh’s intentions were clearly demonstrated Stukley moved to arrest him once again. The failed attempt ended with Sir Walter, who until then had been treated as a prisoner at large, once again locked up in the Tower of London, there to await his fate at the King’s pleasure.

Sir Walter Raleigh was an Intriguing Man in History
Although Raleigh prepared documents in his defense affixed with his seal of office, they were not presented to his accusers, nor the king. Wikimedia

33. Raleigh was not given an additional hearing or trial following the Orinoco engagement

During his prolonged journey from Plymouth to London (and likely on the voyage home from the Orinoco as well), Sir Walter Raleigh prepared a defense against the charges levied by the Spanish government against him. He had copies of the written orders he had provided Keymis, forbidding any hostile action against the Spanish, and his logs and ledgers indicated plainly that he had not been present when the attack occurred. He also had statements from participants in the affair which claimed that the Spanish had attacked the English explorers without provocation, killing his own son in the process, yet he still personally opposed retribution against the Spanish. He was not given a chance to present his arguments to King, court, or magistrate.

Sir Walter Raleigh was an Intriguing Man in History
Emissaries from the King of Spain were among those who pressured James VI and I to order Raleigh’s execution. Wikimedia

34. The Spanish agitated for Raleigh’s execution on the earlier warrant, for which he had been pardoned

With Raleigh imprisoned in the Tower, unable to present a defense against the charges against him, pressure on King James was brought to bear by Spanish ministers, with additional pressure demanded by the Spanish from the French and others present at court. Ironically, Raleigh’s earlier conviction had been for conspiring with – not against – Spain in an alleged attempt to change the succession of the English throne, an irony not lost on King James. Nonetheless Raleigh had been pardoned under pain of death should he violate the conditions prescribed, and though there was little evidence that he had personally, the expedition he had commanded had clearly done so.

Sir Walter Raleigh was an Intriguing Man in History
Though Raleigh had been pardoned and the death penalty commuted via this 1617 Royal Warrant, his enemies demanded his original sentence be carried out. Wikimedia

35. Although Raleigh was not given another trial, there was evidence read against him

Raleigh was not given the benefit of a trial, but during the weeks leading up to the decision by King James considerable evidence was presented against him, directly to His Majesty, and in the broadsheets and public gatherings of the day. Much of it was presented by Stukley, who presented knowledge of plots by Raleigh and his followers to flee to France and take up arms against England. The evidence was not substantiated and in the absence of a court hearing it entered the record unchallenged. Several of Raleigh’s friends suggested the means by which he could be spirited from the Tower and sent into exile, either in Ireland or even America, but nothing came from any of them, as the court of public opinion shifted against him through the false reports of his enemies.

Sir Walter Raleigh was an Intriguing Man in History
Raleigh, according to legend, tested the sharpness of the executioner’s blade before placing his head upon the block. Wikimedia

36. Raleigh was executed for treason on October 29, 1618

When Sir Walter Raleigh mounted the scaffold to face his executioner, it was for the crime of High Treason for which he had been convicted in 1603, and for which he had been pardoned fourteen years later. He was allowed to speak before sentence was carried out, and in doing so he denied the charges against him and forgave his enemies, including specifically by name Sir Lewis Stukley. He was beheaded by axe. Stukley quickly fell into public disrepute as the depth of his personal dislike of Sir Walter became known, and as evidence of a long-standing grudge between the Stukley and Raleigh families came to light.

Sir Walter Raleigh was an Intriguing Man in History
Elizabeth Raleigh, nee Throckmorton, kept her late husband’s embalmed head for the rest of her life. Wikimedia

37. Raleigh was only partially embalmed though he was given a Christian burial

The head of Sir Walter Raleigh was the only portion of his body to be embalmed, as preliminary to giving it to his widow. His body was buried in St. Margaret’s at Winchester, where his tomb is today a shrine. Raleigh’s head remained in the custody of his wife, kept in a bag of velvet, until her death, when it was reunited with his body in the grave. Whether Raleigh was guilty of the crime for which he was executed has been debated ever since, and even during his lifetime one of the judges at the trial which eventually cost him his life wrote, “The justice of England has never been so degraded and injured as by the condemnation of the Honourable Sir Walter Raleigh”.

Sir Walter Raleigh was an Intriguing Man in History
Walter Raleigh was not the first to use tobacco in England, though his writings popuarized it in Europe and later North America. Wikimedia

38. Raleigh and tobacco

It is not known for certain when and where Sir Walter Raleigh first experienced tobacco, though he was reported to have used it during the attack on Cadiz. He became an ardent consumer of tobacco, and later in life a strong supporter of its use, as well as its cultivation as a means of making the English colonies in North America financially successful. He popularized its use in England and Ireland, wrote poetry espounding on its benefits, and left behind in his cell in the Tower of London a small tobacco pouch, with an inscription in Latin. When translated the inscription read, “It was my companion at that most miserable time”.

Sir Walter Raleigh was an Intriguing Man in History
The oft-told tale of Raleigh shielding his sovereign’s feet from the mud with his cloak is almost certainly apocryphal. Wikimedia

39. Raleigh and the age of chivalry

Sir Walter Raleigh is often portrayed as the epitome of chivalry, as in the tale wherein he placed his cloak upon the ground rather than have the Queen’s shoes soiled with mud, a tale which is almost certainly apocryphal. He exhibited the courtly manners of the Elizabethan age, yet in his writings – particularly in his poetry – revealed a link with the commoners of the day. His life was one of improbable adventure salted with long imprisonment; romantic links with the Virgin Queen but a long marriage to but one wife; soldier, sailor, philosopher, poet, historian, explorer, and entrepreneur. He was a living definition of the term “swashbuckler” as were many of his contemporaries, a man of an age long gone by other than to history.


Where do we find this stuff? Here are our sources:

“Sir Walter Raleigh: In Life and Legend”. Mark Nicholls and William Penry. 2011

“Walter Raleigh Biography”. The Biography Channel. 2014. Online

“The Reign of Elizabeth: 1558-1603”. J. B. Black. 1936

“The Favorite: Raleigh and His Queen”. Matthew Lyons. 2011

“Set Fair for Roanoke: Voyages and Colonies, 1584 – 1606”. David B. Quinn. 1985

“Sir Walter Raleigh”. Entry, Tower of London, History and Stories. Tower of London. Online

“Sir Walter Raleigh and the Quest for El Dorado”. Marc Aronson. 2000

“Jersey’s people are made kings of their castles”. Philip Jeune, The Independent. July 6, 1996

“The Sir Walter Raleigh Collection”. Wilson Library, University of North Carolina. Online

“Treasure, Treason and the Tower: El Dorado and the Murder of Sir Walter Raleigh”. Paul R. Sellin. 2011

“The Search for El Dorado”. John Hemming. 2001

“Raleigh’s Last Journey: A Tale of Madness, Vanity and Treachery”. Paul Hyland. 2008

“Sir Walter Raleigh”. Robert Lacey. 1973

“Raleigh and the Throckmortons”. A. L. Rowse. 1962

“The Historie of the World”. Sir Walter Raleigh. 1614

“The Story of Civilization, Volume VII, Chapter VI”. Will and Ariel Durant. 1961