Patricia Bernstein

Famous Prisoners in The Tower of London: Sir Walter Raleigh

Walter Raleigh, one of the most remarkable men in the history of England, spent many years in the Tower of London and was finally executed. But his fame lives on.

William Segar: Portrait of Sir Walter Raleigh (1522-1618), Soldier and Historian, Date 1598 Oil on canvas
Sir Walter Raleigh, attributed to William Segar, Public domain, via Wikimedia Commons

Raleigh’s family was militantly Protestant: Raleigh developed a strong aversion to Roman Catholicism during his childhood. When Queen Mary I (still known as “Bloody Mary”) tried to force the country back to Catholicism, Walter’s father spoke with Protestant martyr Agnes Prest before she was burned, and had to hide in a church tower himself to avoid execution.

Handsome, intelligent and capable, Walter Raleigh studied law, wrote poetry, fought in the religious civil wars in France, suppressed a rebellion in Ireland, and went exploring in the New World, quickly rising in Queen Elizabeth’s favor, gaining vast riches and estates and achieving the title of Captain of the Yeomen of the Guard.

The famous story that Raleigh threw his cloak down on the ground so that the queen could walk over a puddle may be no more than a legend: what young man would sacrifice an expensive item of clothing just when he was trying to make a good impression on the queen? The story was probably first told in Thomas Fuller’s Worthies of England, which wasn’t published until more than 40 years after Raleigh’s death. But that bit of myth is emblematic of Raleigh’s oversized reputation for gallantry and style.

Raleigh is often credited with bringing tobacco to England for the first time in 1586, but there were stories circulating 20 years earlier among sailors returning from the New World that native residents of those far-flung regions walked around with little burning sticks in their mouths, claiming that tobacco protected them from many diseases. Some European explorers thought they should protect themselves in the same way so they began to smoke and brought tobacco back to the Old World.

Raleigh did play a role in popularizing tobacco. According to legend, the first time Raleigh smoked a pipe in his house in England, he was merrily puffing away when a servant, seeing the smoke, thought the master was on fire and threw water on him.

Raleigh’s hot temper occasionally got him in trouble, but he came closest to losing everything he had gained when the queen discovered that he had secretly married Bess Throckmorton, one of her ladies in waiting. Raleigh was in his early 40s and Bess was only 19 when she first came to court to serve as lady-in-waiting to the queen, but they fell madly in love. In 1591, they married secretly when Bess became pregnant.

Elizabeth I much enjoyed her flirtations with the resplendent men of her court and was never pleased to find that they had fallen in love or, worse yet, married without her approval. When the marriage was discovered in 1592, both Raleigh and his wife were sent to the Tower of London. Raleigh was released, however, to supervise the dividing of spoils from a captured Portuguese ship full of jewels, gold and silver coins, fine cloth and tapestries, pepper, cloves, cinnamon, mace, nutmeg, cochineal and ebony.

Eventually he and Bess were both delivered from the Tower and were able to begin their life together in Sherborne while Raleigh, still banned from court, busied himself as a Member of Parliament. Unfortunately, he made a fatal mistake when he publicly questioned the planned succession of James VI of Scotland to the throne upon Elizabeth’s death as James I of England.

Over time Raleigh was restored to Elizabeth’s favor and helped seize the city of  Cádiz, joined the defense against the Third Spanish Armada, searched for the legendary city of El Dorado in South America, and became governor of the Channel Island of Jersey. But Queen Elizabeth died in 1603 and King James I had Raleigh tried and convicted, in a corrupt and shameful trial, for allegedly taking part in a treasonous plot to replace the new king with his cousin Lady Arbella Stuart. King James decided to let Raleigh live but to keep him imprisoned in the Tower. There he stayed in two rooms on the second floor of the Bloody Tower for 13 years.

Sir Walter Raleigh and his wife parting in the Tower of London
Sir Walter Raleigh Parting with his Wife by Charles Kennedy Burt, after Emanuel Gottlieb Leutze , 1846

In time Raleigh’s imprisonment was relaxed enough that his faithful Bess was allowed to visit him: their second son was actually born in the Tower in 1605! Since he could no longer be a man of action, Raleigh devoted himself to writing and produced War with Spain, Instructions to His Son and his famous The Historie of the World in five books, which became immensely popular. Having become friends with James’ neglected Queen Anne, Raleigh even served as tutor to young Henry, Prince of Wales.

In 1616, partly because of the pleading of James’ favorite George Villiers, Raleigh was released from prison and assigned the mission of searching for gold in the supposed land of El Dorado. He was ordered, however, to injure no Spanish subject during the process, on pain of death. In the meantime, through a circuitous series of events, King James, rather than cancel Raleigh’s voyage, ended up giving Raleigh’s complete itinerary for his trip to the king of Spain, thus effectively stabbing Raleigh in the back before he even set sail.

A skirmish between English and Spanish on the banks of the Orinoco River in Venezuela led to the death of Raleigh’s son Wat and sealed Raleigh’s fate. He was arrested on his return to England. It was said that, during his journey from Plymouth to London, he passed up many opportunities to escape. Maybe he was just too weary and demoralized by the “thanks” he had received for his many exploits on behalf of the Crown.  On October 29, 1618, Sir Walter Raleigh was beheaded in the Old Palace Yard at the Palace of Westminster.

Perhaps Raleigh’s most famous poem was “The Nymph’s Reply to the Shepherd,” in response to Christopher Marlowe’s “The Passionate Shepherd to His Love,” which begins,

Come live with me and be my love,
And we will all the pleasures prove…

Raleigh has the nymph reply (first and last stanzas),

If all the world and love were young,
And truth in every shepherd’s tongue,
These pretty pleasures might me move,
To live with thee and be thy love…

But could youth last, and love still breed,
Had joys no date, nor age no need,
Then these delights my mind might move
To live with thee and be thy love.

Order A Noble Cunning

Sir Walter Raleigh's Bloody Tower of London Room
Sir Walter Raleigh’s Bloody Tower of London Room
Photo by author Patricia Bernstein


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