Sir Walter Raleigh
Episode 166: How the Elizabethan Golden Boy Flew Too Close to the Sun
1588 portrait of Sir Walter Raleigh by an anonymous artist
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Sir Walter Raleigh is a fascinating historical figure who left a deeply powerful impact on the future of the world. In fact, one could argue that, without Raleigh, I wouldn’t be speaking English right now. I’m not being dramatic. It’s not too farfetched to say that, without Raleigh, England may not have conquered the land we now call the United States. Someone would have no doubt, Spain, or France, maybe. But, without Raleigh, it might not have been England, so strong was the power Sir Walter Raleigh wielded in the late 1500s when that conquest first began. Who do you think came up with the name Virginia? A tribute to the virgin Queen Elizabeth I? Raleigh did of course, her favorite courtier and confidante, Captain of the Queen’s Guard. And yet, despite this powerful influence over what our world looks like today, very few people know the first thing about Sir Walter Raleigh. Who was he really? And how did he go from the queen’s favorite golden boy to beheaded at Westminster in the span of just a few decades? Let’s fix that.
Hello, I’m Shea LaFountaine and this is History Fix, where I tell surprising true stories from history you won’t be able to stop thinking about. I have wanted to talk about Sir Walter Raliegh for such a long time. I think he is a super important and yet vastly misunderstood historical figure and I think a large part of that is because of his ultimate fate. In the end, Raleigh was executed. He was beheaded for treason. And I think that if that hadn’t happened, we would know a whole lot more about him today. Instead, we’ve had to piece him back together through shreds of evidence, fragments of records and writings, most of which have not survived. They weren’t singing Raleigh's praises in the end. They were hushing him up. They were trying to forget him. And so, much of the record of who Sir Walter Raleigh was has been lost. But we know that he was a very important person in the late 1500s because, without him, it’s likely Queen Elizabeth would never have sent the first group of English colonists to the Americas in the 1580s. That was all Raleigh.
Before we get into the story of Raleigh’s life and his rise to power and his fall from grace. I want to try to explain to you the type of person Raleigh was. Raleigh was a character. He’s often described in contemporary accounts as flamboyant which I think is a good word for it. His clothing is a good example of this, the way he dressed. He famously dressed in extremely elaborate over the top clothing, even for the Elizabethan era which was already kind of over the top. His portraits show him wearing pearls, jewels, elaborate lace, embroidered clothing, fur, and enormous ruffs. His clothing was so extravagant that other courtiers reportedly complained about it. Like “seriously Raleigh, chill dude. Tone it down a notch” as I straighten my own ridiculous ruff. What we can tell from witness accounts from the time and from his portraits is that Raleigh deliberately made himself visually spectacular. He stood out in a crowd.
And his personality followed suit. He was very, probably over confident. A contemporary description calls him quote “damnably proud.” He was very outspoken, he’d tell you his thoughts, you know, no filter sort of thing. He could be very boastful, argumentative, and arrogant. He was not afraid to challenge powerful people which would eventually become a problem but Elizabeth didn’t seem to mind. He was very theatrical, grandiose. I have a feeling he was the sort of person that you either loved or you hated. And, luckily for Raleigh, Queen Elizabeth seemed to love him. There’s a story, that’s probably not actually true, about Raleigh winning the queen’s favor by taking off this super expensive, nice cloak he was wearing and laying it over a puddle so that she could walk over it. That story arises later, you know, there’s no actual contemporary evidence that that happened but I think the story stuck because it was so Raleigh. It was something that he would actually do. It was very believable for him. But how did he get there? How did he get to the queen’s inner circle like that? Let’s back it up to the beginning.
Sir Walter Raleigh was born in Devon, England around 1554. His parents, Walter Raleigh and Catherine Champernowne had both been married before and had children from their previous marriages so Raleigh had several full siblings but he also had 6 half siblings, three from his mother and three from his father. This made Raleigh the youngest of 9 children, and 7 of the 9 were boys. This explains a lot about his personality, I think. To be the baby of that family, you have to have a strong character. You have to be loud and outspoken and attention seeking just, you know, to not fade away and become invisible. Raleigh, I think, drew attention to himself because he had to. His family was relatively well off and well connected. His mother’s aunt had been governess to Elizabeth I when she was still a princess and so they had that connection to the royal Tudor family. His maternal half brother Humphrey Gilbert, was a prominent explorer and a member of Parliament, as was his full brother Carew Raleigh. So they’re, you know, they’re not nobodies.
Of note, Raleigh’s family was devoutly protestant. Some context, he lived not too long after the Protestant Reformation. Elizabeth’s father, Henry VIII had broken with the Catholic church in the 1530s, Raleigh was born in the 1550s. But between Henry and Elizabeth we have the reign of the oldest Tudor daughter Mary I. And Mary was very Catholic. Her mother, Catherine of Aragon, Henry’s first wife had been a Spanish princess. Spain was very Catholic. But also, the only reason Henry even broke with the Catholic church was to divorce her mother. So Mary’s like “screw that, we’re doing Catholicism.” And so Raleigh’s very protestant family had experienced some persecution during Mary’s reign which was from 1553 to 1558 so, the first 4 years of Sir Walter Raleigh’s life pretty much. And so, from that very early age, Raleigh developed a hatred really of Catholicism that would last for the rest of his life.
Like most boys of his social class, Raleigh went to Oxford, although he never graduated. Instead, when he was 17, he went to go fight in France in the Wars of Religion. These were a series of civil wars fought between Catholics and Protestants, in France. Specifically, Huguenots, which were French protestants. So Raleigh went to fight with the Huguenots. Why is he fighting in a civil war in a different country? It’s not just because he hates Catholics and he’s gone rogue. Queen Elizabeth strategically sent Englishmen over to France to help the Huguenots. Because a Huguenot victory would weaken the French government, France was one of their rivals, and a Catholic defeat would help protect England from Catholicism which Elizabeth, like Raleigh, was not into at all. And so at 17, Raleigh followed his half brother Humphrey Gilbert into battle with the Huguenots in France.
And then after that, cause they’re all buddy buddy now I guess, Raleigh joins Humphrey Gilbert on a failed expedition to North America in 1578. They were going to go find a place for an English colony at that point, 1578 but it’s a disaster pretty much from the start. It’s poorly managed. They have way too many ships first of all - 11 ships. And it’s really poorly managed. There are all sorts of disagreements and disciplinary problems. Disease is particularly bad. Food and supplies become a problem and so they give up fairly quickly and return to England before ever reaching the Americas. Raleigh ends up going and fighting in Ireland instead which is where he really catches the attention of Queen Elizabeth. But, I think that, albeit failed, expedition to the Americas in 1578 left quite an impression on him. I think it gave him a taste of exploration that he could not quite satiate any other way. And I think that’s why he circles back around to this idea later. Also, though, another powerful motivator for him was what happened to his half brother Humphrey Gilbert. Humphrey Gilbert doesn’t give up when that 1578 expedition turns back. His patent from the Queen to explore the Americas is still good and so he actually goes back on another expedition in 1583 and ends up landing in Newfoundland, modern day Canada, and claiming it in the name of the Queen. And then he starts to head farther south down along the east coast of what is now the US to find a better place for an English colony but his flagship, which was called Squirrel gets lost at sea and he dies, he goes down with the ship, presumably. And so there’s some unfinished family business here. You know, Raleigh’s brother tried and failed to find a suitable location for an English colony in the Americas and I think, it some ways the torch gets passed to Raleigh. I think he feels some pressure to accomplish what his brother set out and failed to do.
But not yet. Let’s go to Ireland first. Raleigh goes to fight in Ireland in 1580 to help suppress an uprising there and he catches the attention of the Queen and he’s invited to court. She is enamored of his good looks and his gallantry, right the laying down of the cloak over the puddle, that sort of thing. She likes his bold flamboyancy. She is smitten with Raleigh. They have this very playful, flirtatious, best friends bordering on lovers type relationship. And we can see this in some shreds of evidence that get left behind. Raleigh was a poet. I don’t know if you knew that about him. He was a soldier and an explorer, a courtier, and also a poet. Most of his poems have been lost but quite a few have survived. And he wrote this whole series of poems about the Greek goddess of the moon and of the hunt, Cynthia. She’s basically the Greek equivalent of the Roman goddess Artemis. But Raleigh writes poems about Cynthia and Cynthia is clearly actually Queen Elizabeth. We know that Elizabeth’s nickname or sort of pet name for Raleigh was Water. Like Walter but without the L, Water. And so when Raleigh writes in one of his Cynthia poems that Cynthia, as the moon, has complete power over the tide, over the water. He’s really talking about Queen Elizabeth having complete power over him, over Water. And we see more clues about their relationship in his most famous portrait, the cover for this episode, and you’re seeing it now if you’re watching the video version of this episode on either Youtube or Patreon. In this portrait of Raleigh from 1588 we see he’s wearing her colors, black and white. He also has her emblem, which was pearl, he has a pearl earring in his left ear. And if you look very closely in the top left corner of the portrait is a crescent moon. This is of course a nod to Elizabeth as the goddess of the moon Cynthia, in Raleigh’s poems. And so we have all these little secret clues left behind that tell the story of their relationship, their friendship. Now, was it romantic? Were they romantically involved or was this just a plutonic friendship? That’s really hard to say. There’s no evidence at all that they were romantically involved. Elizabeth is famously the virgin queen. She chose very intentionally to never marry. She did not want to share her throne with a man. Did she have love affairs with men? Possibly, maybe, but there’s no evidence.
We do know that Elizabeth really, really favored Raleigh though. She had him knighted in 1584 which is where the Sir comes from. She gave him a position in Parliament which came with vast estates in Ireland. She let him live at Durham House, this very posh mansion in London. She made him captain of the Queen’s Guard which annoyed some of her other courtiers who had been around much longer, like Robert Devereaux, he sort of got passed over for that position. And so really, Raleigh rose through the ranks really really quickly because the queen just took a special liking to him. And so when, in 1584 Raleigh goes “hey, you know what, let’s have another go at this English colony in America thing,” Elizabeth is all ears.
Raleigh’s reasons for wanting this colony were multifold. I think he wanted to finish what his half brother Humphrey Gilbert set out to do and died trying to do. Also, Raleigh wants this colony to mess with Spain. He doesn’t like Spain. Spain is Catholic and Raleigh hates Catholics, because of that persecution his family experienced when he was like 4 years old under the reign of Mary I, daughter of a Spanish princess. So he goes to Elizabeth and he goes “you know what we need to do? We need to set up that English colony in the Americas after all. We need to put it right on the east coast of North America and that way we have a sort of home base that we can use to attack Spanish ships as they travel to and from their colonies in Central and South America.” The main goal of the English colony was to mess with Spain. To attack Spanish ships and to privateer, to steal all the gold and riches they were hauling back to Spain that they had stolen from the Aztecs and the Inca. That’s why Raleigh and Elizabeth want this colony. And Elizabeth agrees to go for it, whatever Raleigh wants, her favorite. But under one main stipulation, Raleigh cannot go. He cannot go with the expedition. He cannot go to the Americas. Not again. She won’t risk losing him. And he’s super bummed about this, you know, he definitely wanted to go. But he is forbidden from joining.
So over the next few years England sends 3 different groups to the coast of modern day North Carolina, an area that Raleigh named Virginia, after the virgin Queen Elizabeth. The first group, led by Philip Amadas and Arthur Barlowe in 1584 is a scouting expedition, to find a suitable place for the English colony. They make a very poor choice and decide on Roanoke Island which is nestled between the barrier islands of North Carolina’s Outer Banks and the mainland. The second group in 1585 is a group of soldiers led by Ralph Lane. They go to set up a fort, Fort Raleigh, start building infrastructure so that women and children can be sent over next. This is a complete disaster. Lane screws this up spectacularly when he murders the leader of the local indigenous people, Wingina and flees back to England, literally running for his life. And then unbelievably, a third group including women and children is sent over in 1587 to establish the permanent colony which famously goes missing becoming the fabled “Lost Colony of Roanoke.” That was a very brief summary. I have multiple whole episodes about this story if you missed them. Episodes 27 and 28 about the Roanoke colonies and then an update episode 114 about some new evidence coming from Hatteras Island that pretty much proves the 1587 colonists went there to live with the Croatoan indigenous people at their village in modern day Buxton. Please do dive into all that if you’re unfamiliar with the story. I’ll link them all in the description. But what you need to know for this story is that Raleigh and Elizabeth’s attempt to colonize North America was an utter and complete failure.
Most of that was due to bad leadership, ahem Ralph Lane. But war with Spain also got in the way. When the governor of the 1587 colony, John White, returned to England for supplies soon after their arrival on Roanoke Island, England was at war with Spain and making preparations to take on the fearsome Spanish Armada in the English channel to defend themselves. White could not get a ship to return to the colony for 3 years. England had bigger problems. They were being attacked and it seemd like, at this point, Elizabeth and Raleigh had forgotten all about Roanoke and the colony plan. They’re focused on Spain now. This Anglo-Spanish war they’re in would eventually end in a stalemate. No one would win. But the English did defeat the Spanish Armada in the English channel and this was very much an underdog victory. This was a big deal. And Sir Walter Raleigh took part in that victory, further securing the favor of Queen Elizabeth.
But then, soon after, it all falls apart for Raleigh. He gets married. He marries Elizabeth “Bess” Throckmorton who was one of Queen Elizabeth’s ladies in waiting. And he must have known that the queen was not going to be happy about this because he marries Bess in secret in 1591. They secretly get married and Queen Elizabeth doesn’t find out about it for a year. She finds out in 1592 and she is furious. She demanded absolute loyalty and she viewed this secret marriage to her lady in waiting as a huge betrayal. To make it worse, the couple already had a newborn son named Damerei Raleigh. I’m assuming that’s what let the cat out of the bag. She’s like “Bess, whose baby is that? Oh.” And I think there was probably a lot of jealousy at work here, the thought of Raleigh giving his affection and devotion to another woman. And also the fact that it was done in secret and kept from her intentionally had to have stung a little. And Elizabeth is so upset, and she feels so betrayed and blindsided by this that she throws Raleigh and Bess and their newborn in the Tower of London. She imprisons them. The baby ends of dying of the plague, and then Elizabeth feels really bad so she lets Bess out and then she releases Raleigh a few months later. But their relationship never recovers. She banishes him from court for 5 years. Raleigh is dead to her. And you might look at that reaction, that possibly overreaction as proof that Elizabeth and Raleigh were romantically involved. You know she was clearly not happy that he had taken a romantic interest in someone else. But I think it was more than that. I think it was the secrecy and the way he had concealed it from her and sort of bypassed her authority. It was a serious breach of court rules and royal authority. They were supposed to get permission from her. A lady in waiting, Bess, had to get permission from Elizabeth to marry and they hadn’t done that. And so, she felt completely betrayed by Raleigh whom she had always spoiled with her favor. He had this extraordinary position at court all because she decided to give to him. Not really because he deserved it. There were others more deserving but she had given it to him and he had stabbed her in the back with it. So it’s not necessarily that she was mad he was romantically involved with another woman. It’s that she was mad he had circumvented her authority after all she had done for him.
So Raleigh is banished from court for 5 years. He goes about trying to win back the favor of the queen. He writes most of his Cynthia poems during this time, describing his despair at having lost royal favor. He also goes on this sort of far fetched quest to find El Dorado, the mythical city of gold that people thought was real at the time. He goes to Guiana, modern day Venezuela to look for El Dorado. He explores the region pretty extensively. He attacks a Spanish settlement and captures the Spanish governor. England is still at war with Spain so this is okay at the time. He sails up the Orinoco river looking for El Dorado. He meets indigenous people and he’s like “where’s the city of gold?” and they’re like “we have no idea what you’re talking about. Who even are you?” And he eventually returns to England in 1595, without finding El Dorado. But then he writes a book about his expedition called The Discoverie of the Large, Rich, and Beautiful Empire of Guiana in which he vastly exaggerates what he actually found there in order to keep the door slightly ajar for the possibility of someday actually finding El Dorado which he still thinks is real.
Anyway, he returns to court in 1597, his 5 year exile has ended. He’s going on and on about this trip to Guiana and the riches and El Dorado, but he gets a cold reception from Elizabeth. She never again showers him with the favor she once did and then she dies in 1603 childless and the crown passes to her first cousin twice removed, King James VI of Scotland who becomes King James I of England. James was the great grandson of Margaret Tudor who was the older sister of Henry VIII, Elizabeth’s father. So James takes over the throne of England and, honestly he’s not very well liked, probably mostly because he was Scottish. He was also king of Scotland and that was kind of icky for the English at the time. But James was very intent on keeping the peace. There had been a lot of fighting during the reign of Elizabeth, particularly with Spain and James wasn’t about that. But then we have Raleigh still at court going off about El Dorado and his hatred of Catholicism and the Spanish and how England should kick Spain out of Guiana and take it for themselves. And this was very at odds with the way James hoped to run things. He wanted to smooth things over with the Spanish and Raleigh wanted to rile them right back up. Also, he wasn’t quite as taken with Raleigh’s flamboyant charms as Elizabeth had been. He’s annoyed by Raleigh quite frankly. He’s like “who the heck is this dude? Who let him in here?” And so he wastes no time in finding any reason to get rid of Raleigh.
What ends up happening is a secret plot, a conspiracy, these were always happening, but there’s this plot that arises to overthrow King James and replace him with Lady Arabella Stuart who is his cousin. They were both equal amounts related to Elizabeth and so people felt she had a claim to the throne too. The plotters, apparently, go to Raleigh and try to get him to help them do this. It’s all uncovered, there’s no actual proof at all that Raleigh helped them or even agreed to help them, but he’s implicated in the whole thing and so James has him imprisoned in the Tower of London, for the second time now. He was actually sentenced to death this time though, for treason, right taking part in a plot to overthrow the king. That’s treason. So in 1603, Raleigh is in the Tower of London and he thinks he’s about to die. He writes this really heart felt, poetic letter to his wife Bess which concludes quote “My dear wife farewell. Bless my poor boy. Pray for me, and let my good God hold you both in his arms. Written with the dying hand of sometimes thy husband, but now alas overthrown. Yours that was, but now not my own. Signed WR for Walter Raleigh” end quote. I mean, the man is nothing if not dramatic y’all.
But he doesn’t end up being executed, that time. James changes his sentence to life imprisonment instead, which sounds terrible but it’s actually not that bad. His wife and child, cause they’ve had another son at this point, Walter who they called Wat, they are allowed to come live with him at the Tower of London and they have like really nice accommodations there, they have servants and everything. It’s not that bad for, you know, someone who’s been charged with treason. But he can’t leave, you know, he is imprisoned there for 13 years actually, during which time he just does whatever the heck he wants pretty much. They have two more sons while he’s imprisoned, Carew and Philip. He grew exotic plants from seeds. He’s like “hey guard, give me that seed catalogue, I gotta place an order.” And when I say exotic I mean like citrus fruits and tobacco cause those were considered exotic in England at the time. In fact, Raleigh helped introduce and popularize tobacco in England. Tobacco is native to the Americas, as are potatoes which he also helped introduce. So he’s not just a soldier, explorer, courtier, poet… he’s also a bit of a botanist and also an apothecary. While imprisoned he concocted his balsam of Guiana which had 40 different ingredients, including ambergris, a secretion from the intestines of a sperm whale. How he is getting that in jail, I don’t know. Says a lot about the level of freedom he had while imprisoned. Oh and he also wrote a book called the Historie of the World. He had access to an extensive library at the Tower of London, over 500 books which he used used as reference material to write his own book. He was writing it actually for the Prince of Wales, King James son Henry who would come to visit him at the Tower. Henry was a big Raleigh fan. He once said quote “only my father would cage such a bird.”
Now, it might sound like Raleigh is having a blast in prison but he is actually quite unhappy, not unlike a caged bird. He actually attempted to take his own life early on with a table knife. Of this, the Lieutenant of the Tower, Sir John Peyton said quote “I never saw so strange a dejected mind as in Sir Walter Raleigh. I am exceedingly cumbered with him; five or six times a day he sendeth for me in such passions as I see his fortitude is impotent to support his grief,” end quote.
In 1616 James released Raleigh from the tower after 13 years of imprisonment, but he doesn’t pardon him. He still technically has a treason conviction. And, believe it or not, he sends Raleigh back to South America, back to Guiana, Venezuela to go look for El Dorado once again. And part of that is probably due to the extremely exaggerated account Raleigh recorded in his book back in the 1590s The Discoverie of the Large, Rich, and Beautiful Empire of Guiana which he really wrote to try to impress Elizabeth and get back her favor but which was mostly made up. James is like go find all this stuff you said was real. And Raleigh’s like “okey dokey!” and he sets off for Guiana for a second time. This one would end in complete disaster though and ultimately seal his tragic fate.
Remember that one of James most important goals as king was maintaining peace with Spain, partly because he wanted to marry his son to a Spanish princess. Well, Spain is all over South America. In fact, Raleigh really downplayed in his book how much Spain had already claimed over there. He made it seem like Guiana and possibly El Dorado were just sitting there waiting, ripe for the English to pluck. But Raleigh promises to leave the Spanish alone and you know, to behave with diplomacy. He’s not going to incite any conflicts with Spain. He’s not even going to go anywhere near the Spanish. He promises that. Except what he doesn’t tell the king is that the Spanish are everywhere and he can’t really avoid going near them. So he immediately sails into known Spanish territory, attacks and burns down a Spanish settlement, killing the governor. There’s some debate over how much of that was Raleigh’s fault. He was not in good health at the time and had put another man in charge. But, ultimately, he was in charge of this expedition and it had done exactly what he promised not to do. His son Wat was also killed in that conflict. So, his son is dead, he’s doublecrossed the king spectacularly, and he returns to Spain without a single fleck of gold to show for it.
James is understandably upset. He accuses Raleigh of deliberately inciting war with Spain. He basically has to punish Raleigh in order to halfway try to repair relations with Spain at this point which have been completely shattered. And so he throws Raleigh back in the Tower of London and he invokes the original sentence for the treason that he was convicted of 15 years ago, execution by beheading. There is no leniency this time. In October of 1618, Sir Walter Raliegh is beheaded at the Palace of Westminster at the age of around 66, which is honestly pretty old for the early 1600s, dude had a good run. According to Historic Royal Palaces, quote “Sir Walter Raleigh faced his fate with brave resolution, and supposedly told his executioner, when waiting for the axe to fall: 'Strike, man, strike!'” end quote.
Then it gets weird. After his execution, Raleigh’s head was embalmed and given to his wife Bess who kept it in a red velvet bag until she died 29 years later. Apparently this bag still survives, this red velvet bag. It is owned by a descendent of their son Carew, talk about a freaky family heirloom.
So that’s Sir Walter Raleigh, but, you know, I think we’ve only really scratched the surface here. I feel like I could make a whole podcast just about Raleigh and trying to uncover who he really was. Because, he’s a really tricky historical figure to nail down. He was very much in the spotlight for a lot of his life. He brought a lot of attention to himself. He held very prominent positions. And so, he was very well known for a time, but well known sort of in the way of a celebrity where there’s a lot of gossip and there’s a lot of false information going around. Even these primary sources, these contemporary accounts of Raleigh, it’s hard to say how much of that is true. Raleigh had a lot of haters. When you live bold and loud and proud like that AND you have the favor of the queen. You aren’t going to be very well liked by those with less favor who feel more deserving of what you have. And then he has this really spectacular fall from grace with Elizabeth but also with James who only barely tolerated him to begin with. And a lot of what’s left behind by Raleigh is destroyed because of that. A lot of his poems and other writings are lost. But what we do see when we examine the shreds of what he left behind, is someone who accomplished an incredible amount in his lifetime.
Sir Walter Raleigh spent his life chasing greatness. He fought in foreign wars, won the favor of a queen, helped spark English colonization of North America that would continue under the reign of King James with the first successful English colony, Jamestown. Raleigh sailed across the Atlantic in search of riches, the mythical golden city of El Dorado. He became one of the most famous men in Elizabethan England. But his greatest strength was also his greatest weakness: he could never stop reaching for more. Even after imprisonment, disgrace, and years of failure, he remained convinced that somewhere beyond the horizon was the fortune and glory he had been chasing all his life. In the end, that obsession would cost him everything. In 1618, the man who had once been one of England's most powerful and celebrated birds was led to the scaffold and executed. Raleigh had spent decades searching for a legendary city of gold, but perhaps the greater mystery is why he could never stop searching. He conquered battlefields, crossed oceans, survived prisons, and stood beside kings and queens—but in the end, the greatest thing he could never conquer was his own ambition - a strength, but ultimately a weakness.
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