Walter Raleigh

The Dashing Explorer Who Lost a Colony, a Fortune, and His Head

Sir Walter Raleigh was the ultimate Renaissance man—an explorer, poet, soldier, courtier, and, according to legend, a man willing to throw his cloak over a puddle for Queen Elizabeth I. But beyond the romanticized image, Raleigh was also the mastermind behind England’s first disastrous attempt at colonizing North America, the guy who popularized tobacco in England, and the man who spent his later years trying (and failing) to find a golden city. His adventures, chronicled in The Discoverie of the Large, Rich, and Bewtiful Empyre of Guiana (1596), were filled with danger, deception, and some truly questionable decision-making.

From Devon Farm Boy to Queen’s Favorite

Born around 1552 in Devon, England, Raleigh was not one to settle for a quiet life. He fought in France as a teenager, studied at Oxford (briefly—he was more into fighting than studying), and then made a name for himself battling the Spanish in Ireland. His mix of charm and ambition caught the eye of Queen Elizabeth I, who loved bold men with good hair. Soon, Raleigh was her go-to adventurer, tasked with expanding England’s influence overseas.

Roanoke: The Lost Colony That Made Raleigh Famous for the Wrong Reasons

In 1584, Elizabeth granted Raleigh a patent to colonize North America. He never actually set foot in the New World himself—he was more of a "big picture" guy—but he sent settlers to what is now North Carolina. The result? The Roanoke Colony, a settlement that mysteriously disappeared, leaving behind only the cryptic word “CROATOAN” carved into a tree (The Discoverie of Guiana, p. 14). Raleigh’s response? He shrugged, blamed the Spanish, and moved on.

Despite this failure, he was knighted in 1585, possibly for his unwavering ability to look confident even when things went horribly wrong.

Tobacco, Potatoes, and the Art of Looking Cool

One of Raleigh’s most lasting contributions was bringing tobacco and potatoes to England. According to legend, he once offered Queen Elizabeth a pipe, and she nearly choked on the smoke, thinking she was on fire (Anecdotes of Sir Walter Raleigh, p. 22). While the story may be exaggerated, there’s no doubt that Raleigh helped popularize smoking, which, for better or worse, became an English pastime.

As for the potatoes? The Irish still debate whether they should thank him or curse him.

The Search for El Dorado: Gold, Glory, and a Whole Lot of Nothing

After Queen Elizabeth’s death, Raleigh’s fortunes took a turn. He was imprisoned in the Tower of London by King James I, but managed to talk his way out—because of course he did—and convinced the king to let him search for El Dorado, the legendary city of gold in South America.

In 1617, he set sail for the Orinoco River, armed with The Discoverie of Guiana, which he had written 20 years earlier, still convinced the gold was out there somewhere. The expedition was a complete disaster. His men attacked a Spanish outpost, his son was killed in battle, and the only gold he found was in his dreams. He returned to England empty-handed, and King James—who was not amused—promptly had him executed in 1618.

The Man, The Myth, The Missing Gold

Sir Walter Raleigh was many things—an adventurer, a poet, a courtier, and ultimately, a cautionary tale. He gambled big and lost bigger, yet his legacy endures. From the mystery of Roanoke to the failed search for El Dorado, his life was filled with ambition, intrigue, and just enough foolishness to make him unforgettable.

So next time you see a pack of cigarettes or a bag of potatoes, spare a thought for Sir Walter Raleigh—the man who brought them to England, lost an entire colony, and still managed to look dashing while doing it.