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Life as a royal favorite was a minefield, a complicated dance, a never-ending game of chess. If you took the wrong side in a negotiation, failed to deliver on a promise, or interfered with the monarch’s sense of security, you could be tried for treason and executed. These three men—Thomas Cromwell, Robert Devereux, and Walter Raleigh—each crossed the line and were beheaded by their beloved monarchs.

Dealing with the king’s impatience

Thomas Cromwell (1485?1540) was Henry VIII’s ruthless and all-powerful advisor. He oversaw the end of Roman Catholicism in England and cleared the way for Henry to marry three wives: Anne Boleyn (beheaded), Jane Seymour (died), and Anne of Cleves (status changed to “beloved sister”). His downfall came after this last mismatch.

At the time of this letter, Henry was still impatiently awaiting the arrival of Anne of Cleves to England, and Cromwell conveys this impatience to the king’s ambassador in Cleves: the king does “marvel at this your long protracted silence.” The letter was so important and urgent that he signed two copies of it, to be sent by two different routes. When Henry rejected Anne of Cleves, saying that “his nature has abhorred her,” Cromwell looked weak and foolish for having championed the marriage. In July 1540, Cromwell was beheaded for treason and heresy, Anne of Cleves’s marriage was annulled, and the king married Catherine Howard (beheaded).

Letter from Thomas Cromwell, Earl of Essex, London, to Dr. Nicholas Wotton, 8 November 1539 | Folger X.c.149 (1-2)
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When you look on this, remember me

This is Anne of Cleves’s prayerbook. Her inscription points to her hopes for what could have been. On one of the back pages, she wrote to Henry VIII, her new royal husband, “I beseech your grace humbly when you look on this remember me. Your grace’s assured Anne the daughter of Cleves.” Printed on vellum, the initial letters and woodcuts are hand colored.

Book of Hours (Salisbury) (Paris: Germain Hardouyn, 1533?) | Folger STC 15982
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Hot off the press: Essex is in the tower

Robert Devereux, 2nd Earl of Essex, stepped in as Queen Elizabeth I’s new favorite after the 1588 death of the Earl of Leicester (his stepfather and godfather). Chivalrous, witty, and athletic, he was immensely popular with the public. The events that led to the beginning of his downfall were a failed military expedition and acts of disrespect to the queen. Frustrated by his fall from favor and angry at the courtiers who caused it, Essex led a failed coup in 1601.

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Printed the day after his act of rebellion, this proclamation by the queen announced that the three guilty earls (Essex and his accomplices, the Earls of Rutland and Southampton) were in custody. She reassured her subjects that safety has been restored and urged them to report anyone spreading rumors and slanderous words while she contemplated what to do next.

By the Queene. Whereas the Earle of Essex accompanied with the Earles of Rutland and Southampton, and divers other their complices . . . knowing themselves to be discovered in divers treasonable actions, 9 February 1601 | Folger STC 8279 copy 2

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The traitor list

Essex did not act alone. Other power players, many of them knighted by Essex on the battlefield, joined him. Eighty-seven of them are listed here in order of rank, starting with the Earl of Essex, the Earl of Rutland, and the Earl of Southampton (Rule 5). The failed rebellion was over almost as soon as it had begun, but Queen Elizabeth didn’t take any chances. She had Essex beheaded for treason just 17 days later, with other executions to follow.

List of traitors from the Essex Rebellion, 1601 | Folger X.d.592

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Essex the national hero

Mounted on his horse and resplendent in his military armor, Essex is surrounded by scenes from his military exploits, which in reality were failures rather than successes. His coat of arms and lengthy list of titles emphasize his power player status, while the verse below frames him as an honorable, popular, and beloved hero of the people.

Thomas Cockson, The Right Honorable Robert Deworex, Earle of Esex, 1599 | Folger STC 7758.3 v.3 no.13
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Seeking forgiveness by promising riches

Sir Walter Raleigh, mariner, explorer, and colonizer, was a favorite of Queen Elizabeth until she discovered that he had secretly married one of her ladies-in-waiting. She imprisoned him in the Tower and then released and banished him from court for five years. During this time, and in an effort to return to the queen’s favor, he sailed to South America in a failed search for the mythical city of gold, El Dorado. He then published this book exaggerating his exploits.

Sir Walter Raleigh, The discoverie of the large, rich, and bewtiful empyre of Guiana (London: Robert Robinson, 1596) | Folger STC 20636 copy 2

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Raleigh’s last chance

Raleigh’s fortunes plummeted after the queen’s death and the accession of James I. Raleigh was sentenced to death for allegedly plotting against the king. At the last minute, James reduced Raleigh’s sentence to life imprisonment in the Tower. Raleigh’s continued promises of gold in Spanish Guiana (today, in eastern Venezuela) convinced the king to release him fourteen years later. These “letters patent” with James I’s Great Seal authorized Raleigh’s release “in hope he may and will prove serviceable to us and our state.” But Raleigh’s return to grace was short lived. The voyage was a disaster, the king was infuriated, and ultimately Raleigh was beheaded for treason.

Warrant under the Great Seal for the release of Sir Walter Raleigh from the Tower of London, 30 January 1617 | Folger L.b.358
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Managing the message

Raleigh was known for his brilliance and brashness, defending his honor to the very end. His eloquent “scaffold speech” circulated widely. His calm and brave demeanor and his refusal to be blindfolded for his own beheading struck a chord. People questioned whether it had been necessary to kill a national hero. In an attempt at damage control, the commissioners who tried him published a legal defense of their actions.

A declaration of the demeanor and cariage of Sir Walter Raleigh, Knight (London: Bonham Norton and John Bill, 1618) | Folger STC 20653 copy 1

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See this exhibition at the Folger

How to Be a Power Player: Tudor Edition
A man dressed in court fashions during the reign of James I

How to Be a Power Player: Tudor Edition

Social climbing was a competitive sport in Tudor England, requiring a complex range of skills, strategies, and techniques. This exhibition explores what it takes to become an early modern mover and shaker.
Through July 2025
Rose Exhibition Hall