Sir Walter Raleigh: Britain’s Greatest Adventurer

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For centuries, his name has been synonymous with adventure. Born in rural Devon, Walter Raleigh managed to rise to the very top of Britain’s fledgling empire. As a soldier, he fought in France’s religious wars and against rebellions in Ireland. As a courtier, he became one of Queen Elizabeth’s closest confidants, able to destroy a rival with a whispered word. But Raleigh’s roles went beyond what society expected of him. A natural adventurer, he led expeditions to modern Venezuela to find the legendary El Dorado and funded the establishment of England’s first colony in the New World. However, while Raleigh thought of himself as an enlightened man, he would be seen very differently—as a political martyr caught on the losing side of Britain’s 1603 transfer of power. Raleigh was imprisoned, tortured, and forced to fight for his very life. Nearly crushed by the system, he wound up rolling everything on one final adventure: a daring attempt to wrestle gold from Spain’s far-flung colonies. What happened next would ensure his name lived on for eternity.

It’s customary for biographies of Walter Raleigh to start by mentioning that he came from modest circumstances, but make no mistake—his background was only modest from the point of view of a 16th-century English aristocrat. At the moment he was born in the rural English county of Devon around 1554, Raleigh was almost perfectly positioned for greatness. His aunt was the governess of the future Queen Elizabeth, while his half-brother was Humphrey Gilbert, a seafaring adventurer whose own life would deeply influence Raleigh’s. So while the family weren’t rich, they certainly were well-connected. However, there was one area where Raleigh’s birth put him at a real disadvantage: his family were hardcore Protestants at a time when a hardcore Catholic was on the throne. This meant only one thing: persecution. Although the family avoided the fate of other Protestants during Mary I’s reign, they were still in constant danger. As a result, Walter Raleigh would grow up to hold an undying hatred toward Catholics.

Their persecution didn’t last long; in 1558, Mary went off to her eternal reward and was replaced by Protestant Elizabeth I. Just like that, the Raleighs could breathe easy again—or at least we assume that was the case. In common with many figures of this era, we know remarkably little about Walter Raleigh’s early life. In fact, after his birth, we can’t say with any certainty what he was doing until roughly 1569. That’s because 1569 is when the teenage Raleigh left Devon to fight in France’s wars of religion. Kicking off in 1562, the wars of religion pitted France’s Catholic majority against its Protestant Huguenots in a brutal fight featuring massacres. Although he fought in France for less than a year, Raleigh witnessed enough human depravity to make a deep impression on him.

When the time came, the teenage boy would himself become adept at the art of bloodshed. Raleigh dropped out of the historical record until 1572 when he turned up studying in Oxford. Doubtless, he made a hell of an impression there. By this time, the boy had grown into a dashing, dark-haired man who towered over most of his contemporaries. He was every young maiden’s dream of a tall, dark, handsome stranger—with one exception: all his life, Raleigh would speak with a strong Devonshire burr, an accent not particularly charming.

The 1570s would see Raleigh embark on two important love affairs: the first was with writing, and the second—far more important—was with exploration. It all started in June 1578 when Raleigh’s seafaring half-brother, Sir Humphrey Gilbert, organized an expedition to try and find the fabled Northwest Passage. Excited by the prospect, Raleigh joined his brother’s fleet as captain of the Falcon, only to witness firsthand the expedition become a disaster. Scattered by storms and damaged by desertions, Gilbert’s expedition eventually gave up on the passage and instead turned to attacking Spanish ships for loot. It was such a failure that it could have put Raleigh off exploring for life. But no—something about the high seas, the adventure, and the privateering seemed to have touched Raleigh’s soul. From that moment on, he was destined for a life of adventure.

The first of these adventures came in the spring of 1580. Jailed for taking part in a brawl, Raleigh got his friends to pull a few strings and instead had him transferred to the army’s officer corps. Before long, he was in Ireland taking part in the siege of Smerwick. The small siege is infamous today because when the fort surrendered to the English, they gave no quarter, butchering everyone inside. One of those who gleefully carried out the mass executions was Walter Raleigh. In the aftermath of the massacre, Raleigh returned to London with some secret documents discovered on the bodies. Although he would spend the next year back in Ireland, his star was already beginning to rise. He was no longer just some Devon boy with a hankering for adventure; he was fast becoming a force to be reckoned with.

Despite stunning lows, Raleigh never had much trouble with the ladies. Although tales of him as a 16th-century James Bond with lovemaking skills to match are later fabrications, we know he caught many a girl’s eye. In Ireland, for instance, he sired an illegitimate daughter, but his biggest catch came in December of 1581. That was the month he somehow turned Queen Elizabeth’s head. A ton has been written about the courtship between Walter Raleigh and Queen Elizabeth I, with the nature of their relationship portrayed as anything from intellectual equals to definitely sleeping together. Certainly, Raleigh seems to have wormed his way into the queen’s heart. Not long after meeting her, he was made squire of the court, and Elizabeth left no doubt that he was her favorite.

On the other hand, many stories—such as Raleigh laying his cloak down so the queen could avoid stepping in a puddle—are almost certainly untrue. Sexual or not, Raleigh proved useful to the queen, and this usefulness paid off big time. From Elizabeth’s perspective, Raleigh was both an astute courtier, writing her elegant poems, and a natural spin doctor—a master of backstabbing, political cover-ups, and justifying controversial decisions. He also seems to have worked as a secret agent on occasion, such as when the queen dispatched him to the Low Countries to personally retrieve a message from William the Silent.

Still, it would be hard to claim Elizabeth wasn’t a little obsessed with her new and handsome courtier. The gifts showered on Raleigh would embarrass a billionaire showing off for his trophy wife. In 1583, Raleigh was gifted the run of Durham House, a magnificent mansion sitting along the Strand. That same year, the queen bestowed upon him a monopoly over wine, effectively meaning everyone selling wine in Britain had to pay Raleigh for the privilege. Two years later, he’d be granted a similar monopoly on broadcloth, plus a knighthood, plus titles like Vice Admiral of the West, Lord Lieutenant of Cornwall, and Lord Warden of the Stannaries—a fancy word for Cornwall’s lucrative tin mines. Oh, and in 1586, he was also granted 42,000 acres in Munster for his service in Ireland—about three times as much as everyone else received.

But while Raleigh’s rise at court was dizzying, it also changed him. The more attention Elizabeth showed, the more Raleigh started living up to her image of him as a dashing, flamboyant adventurer. He started dressing extravagantly, decking himself out in pearls, acting like he was constantly performing for an invisible audience. And in a sense, he was. Later in life, Raleigh would write that it’s better to befriend rich people because only they can give you the money you need to stand on your own two feet. What was his behavior at court but a way to ensure that the money kept rolling in?

By 1587, Raleigh was established enough to be made Captain of the Guard, effectively in charge of Elizabeth’s personal protection, although he’d have to wait until 1591 to take up the post when the current holder died. It still should have been the pinnacle of his career, but by now, Raleigh was already moving on to bigger and better things. No longer content with dreary old England, he had set his sights on conquering the world.

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Weirdly, the best thing that ever happened to Walter Raleigh was probably his half-brother dying. Sir Humphrey Gilbert had been a titan of his age—the sort of guy we should probably cover in his own biographics video. Let us know in the comments if you want that. As long as he was around, Raleigh would always be content to be in his shadow—a man standing beside greatness rather than being great himself. But in September 1583, Gilbert drowned on an expedition at the age of only 43, and simply standing in his shadow was no longer possible. When Raleigh received the news, he made an important decision: he would carry on with his half-brother’s plans alone. At the time of his death, Gilbert had been preparing the grounds for a colonizing expedition to America. Raleigh now picked up those plans and ran with them, assembling a team at Durham House to make them a reality.

And so began the story of England’s first colony in the New World. Although Raleigh wouldn’t physically help establish it—Elizabeth being unwilling to let him stray too far from court—he would both bankroll it and provide logistics. In 1584, that meant supporting the first scouting mission that sailed to what we now call the Outer Banks of North Carolina and returned with two Algonquian speakers, Juanchis and Manteo. The arrival of these Native Americans in London caused a sensation. It’s worth remembering that at this time, going to America wasn’t simple; it was an operation of bean-dish complexity. One account we read compared it to the Apollo program, with the 1584 expedition being like Apollo’s 7 and 8—basically proving that it could be done. With the success of that expedition, Raleigh and his team were able to pivot to their own moon landing.

In early 1585, Elizabeth granted Raleigh the title of Lord and Governor of Virginia, his colony named after the Virgin Queen herself. That same year, an all-male crew set out to Roanoke Island to establish a temporary camp there that they could use as a base for future expeditions. It lasted less than a year before the men gave up and came home. But Raleigh wasn’t deterred. In spring 1587, the third expedition set out. It would be this expedition that changed history. Hundreds of Londoners left on ships that swept across the Atlantic’s dangerous waters—the 16th-century equivalent of a SpaceX fleet off to colonize Mars. Although it would be later eclipsed by Jamestown, the first colony was the start of something massive. It was Raleigh’s expedition that sowed the seeds of English North America.

From the dizzying heights of the Declaration of Independence to the hideous lows of the Trail of Tears, everything sprang from this one moment. This is curious when you remember that the Roanoke colony was an abysmal failure. Despite boasting the first English child born on American soil, the colony soon ran low on supplies. Governor John White was dispatched to Britain to get help, only for war with Spain to break out, trapping him across the Atlantic. By the time White returned in 1590, the Roanoke colony had been abandoned. All that was left was the word “Croatoan” carved in a post—a reference to both the nearby island and a nearby tribe.

The first English colonists in American history left no sign. Back in London, Raleigh was personally blamed for the colony’s failure and the presumed deaths of its residents. While this isn’t really fair, it still left a stain on his reputation that he struggled to shake off. But while being implicated in the loss of hundreds of lives wouldn’t have been enough to dislodge Raleigh from his position at the queen’s side, what came next would soon turn him into a pariah.

It’s time for Walter Raleigh to get married. To this day, all sorts of legends still cling to Raleigh’s name. For instance, people insist that he introduced both the potato and tobacco to England, having brought them over from Virginia. In reality, the potato spread across Europe after arriving in Spain, while tobacco had reached England as early as 1571. At most, Raleigh probably made smoking a fashionable activity at Elizabeth’s court. Yet his fame was so great that people would attribute the entire concept to him.

But just as odd tales clung to Raleigh, so too did the man himself believe in some wild stuff. While this might have been the legend of El Dorado—the city of gold that was said to exist in South America’s interior—El Dorado’s mirage dragged many Europeans to their deaths over the decades. While Raleigh would survive his own hunt for the city, he swallowed the story as easily as any conquistador. In 1595, he even managed to take four ships up the Orinoco River into modern Venezuela in a bid to get the treasure. No prizes for guessing exactly how much mythical gold he succeeded in bringing back to England.

Just a few years earlier, Raleigh might have been able to shrug off such a failure, but by 1595, things had changed. From Queen Elizabeth’s favorite, he’d now fallen into a position best described as the most hated man in Britain—and he’d done it by breaking the queen’s heart. Back in 1588, around the time the Roanoke colonists were wondering where the hell the fresh supplies were, Raleigh started an affair with Elizabeth Throckmorton, one of the queen’s maids of honor. Elizabeth, better known as Bess, was a strong-willed woman who was easily Raleigh’s equal. Sadly, that sort of instant attraction didn’t count for much when the queen herself was fawning over Raleigh, and the two were forced to keep their affair secret.

This was all fine and dandy until Bess fell pregnant in 1591. Determined to do the decent thing, Raleigh married Bess in secret, and they both kind of just hung around the edges of the court, hoping no one would notice the brand-new baby. It was a dream as quixotic as finding El Dorado. In May of 1592, word of the marriage and the baby finally got back to the queen, who detonated with the force of a thousand H-bombs. Raleigh and Bess were arrested and thrown into the Tower of London. It was only when Raleigh bribed the queen with insane amounts of treasure that she agreed to release him. But by then, it was too late. The baby died the same year it was born, never knowing a normal family life.

Although Bess was likewise released in the wake of the tragedy, both she and Raleigh were banned from court, their names reduced to mud. Still, Raleigh was convinced that this wasn’t the end—that he could charm his way back into the queen’s good books. Certainly, by 1600, Elizabeth seems to have been thawing toward him. Following a successful attack on the Spanish city of Cadiz, Raleigh was made Governor of Jersey. It seemed like the old rake had done it—that he’d used his endless charm and talent for adventure to pull his life back from the abyss. Alas, it was all just a temporary illusion.

Elizabeth I died on March 24, 1603, at the age of 69. Although her death wasn’t a shock, it was still like someone had placed a bomb under Raleigh’s carefully cultivated life. She’d been his benefactor, his protector. Even when he was out of favor, the queen had allowed him to keep his manor and monopolies. Now she was gone, and suddenly the vultures were circling. All those people Raleigh had annoyed in the Elizabethan era by being such a sycophant were out for revenge.

Although Raleigh might have assumed he could turn even this unlucky break around, he was wrong. From now on, things were going to be all downhill. Although his rise had taken decades, Raleigh’s fall was finished in barely half a year. In the wake of Elizabeth’s death, James VI of Scotland descended to the English throne as James I. Already ill-disposed toward annoying adventure-loving fops, when Raleigh first met the new king, he received less a smile than an unimpressed grimace. Still, Raleigh was at least allowed to perform his official functions at Elizabeth’s funeral, but it was just a final nod to the departed queen.

The moment his benefactor was in the ground, Raleigh’s life spectacularly imploded. He was thrown out of his mansion of two decades, Durham House, given barely a fortnight to plan his move. Then he was stripped of his role as Captain of the Guard before losing the right to both his monopolies. It was a humiliating reversal of fortune—a kick in the gut from fate that Raleigh felt was wholly undeserved. Unfortunately, though, this was just the beginning.

To understand what happened next, we need to quickly introduce a couple of characters