The Dudley Dynasty: Family Bonds Forged in Fire

The Making of Robert Dudley, Earl of Leicester: Treason, Tower, Survival, #2 of 3

“He is a traitor; let him to the Tower,

and chop away that factious pate of his.”

- Henry VI, Part II, V.i

Just an ordinary portrait of three creepy guys to brighten up the walls of your chamber, M’Lady. King Henry VII and his hated tax collectors, Edmund Dudley (already wearing red) and Richard Empson.  You can feel their downfall coming.

Before Robert Dudley became Queen Elizabeth I’s favorite or the mighty Earl of Leicester, he was the grandson of one attainted traitor, the son of another, and the brother of a third. Six of his seven brothers would die young. He himself would languish for 15 months in the Tower of London, expecting death carrying a headsman’s ax to come tapping down the stone corridor outside his door.

The Dudley name rose high and fell hard again and again. Robert learned early that wealth, position and power could vanish with a monarch’s whim.

Edmund Dudley (1462-1510): The Architect of Ambition

Robert never met his grandfather. Edmund Dudley, a financial mastermind and trusted advisor to Henry VII who orchestrated the king’s financial policies, squeezing taxes from nobles and gentry alike. But when Henry VII died in 1509, his son, the newly crowned Henry VIII, needed a scapegoat for his father’s greed – and he wanted Edmund’s amassed fortune for himself. Within a year, Edmund Dudley was convicted on a flimsy charge of conspiracy - assembling arms while Henry VII lay dying – and beheaded on Tower Hill. It was a tidy win for Henry VIII. The Dudley name was attainted and the family disgraced, their fortune and lands confiscated by the crown.

Edmund’s son, John Dudley, suddenly became a 6-year-old commoner, but he learned from his father’s mistakes. He rebuilt the Dudley wealth and influence from the ashes of Edmund’s disastrous political downfall.

John Dudley (1504-1553): The Master of the Game . . . Until He Wasn’t

John Dudley did more than restore his family’s standing—he exceeded it. A shrewd soldier, politician, and court manipulator, he became Earl of Warwick, and eventually Duke of Northumberland. Through his service to the young King Edward, John Dudley became the most powerful man in England, other than the King. To cement his power, he wove a web of alliances, marrying his many children into prominent noble families. Robert learned diplomacy and hardball at his father’s side.

As explored in the prior post in this series, The Untold Backstory of Robert Dudley, Earl of Leicester: Queen Elizabeth I’s Favorite, John Dudley orchestrated one of the most infamous succession gambits in Tudor history – trying to place his daughter-in-law, Lady Jane Grey, on the throne.

Here’s what happened next - and why Robert carried out a vendetta against one particular man and his family for the rest of his life.

A Mission Doomed by a De Vere

A dying teenage king’s handwriting—and John Dudley’s plot to put his own son on the throne of England. It started with simply deleting an “’s” and inserting just two more little words: “and her”. It ended in a lot of blood.

To block Princess Mary’s claim to the throne, John dispatched Robert to lead 300 armed men into Hertfordshire and arrest her.  But Robert arrived too late.  Mary had fled the day before, raised her own army in East Anglia, and gained a critical ally -  John de Vere, 16th Earl of Oxford. With Oxford’s support, Mary  prevailed and was declared Queen. 

Robert’s first military command ended in utter and humiliating failure. He returned in disgrace to face the surrender and arrest at Framingham Castle in Norfolk of his father, his brothers, William Cecil and himself. The execution of Robert’s father and brother Guildford followed swiftly. 

Could Robert have defeated Mary if Oxford hadn’t backed her?  We’ll never know.  But Robert never forgot it. And he never forgave.

The Tower of London Year

With their hopes crushed and Guildford’s execution severing any remaining Dudley claim to the throne, Robert with his brothers John, Henry and Ambrose remained imprisoned in the Tower. They had time to do some serious thinking. Of the eight Dudley brothers, two were already dead. The eldest, Sir Henry Dudley (Robert had two brothers named Henry) had been killed fighting for the same Henry VIII who had decapitated their grandfather.  Another brother, Thomas, had died young.  

Some romantics speculate that Robert and Princess Elizabeth fell in love while both were held in the Tower. Accused of treason and of carrying a child by Thomas Seymour, brother to the dead Lord Protector and husband of former Queen Catherine Parr [👉: Firebrand with a Very Particular Set of Skills], Elizabeth was only imprisoned between March and May 1554. It’s improbable that her sister Queen Mary would permit her interaction with the lusty sons of John Dudley. Even if they met as children, there is no record until after her 1559 coronation.  

We do know this: in September 1553, the Dudley brothers’ wives - Elizabeth Tailboys (Ambrose), Anne Seymour (John), and Amy Robsart (Robert) visited their imprisoned husbands. It was a poignant moment, especially because Amy Robsart would die at the bottom of a staircase in 1560, fueling rumors that Robert had planned her murder in order to marry Queen Elizabeth.

All four Dudley brothers walked free in November 1554, thanks to the deft work of a very resourceful behind-the-scenes negotiator, whose identity will be revealed in the next post. But, sadly, John died of illness contracted in the Tower, Henry fell in 1557 at the Battle of St. Quentin in France and the youngest, Charles, not implicated in their father’s plots, also died young. Only two of John Dudley, Duke of Northumberland’s eight sons survived: Robert and Ambrose.

Robert Dudley: A Survivor in a World of Ghosts

John Dudley, Duke of Northumberland: History nearly forgot this Tudor power player who almost rewrote the line of succession. He left his son Robert Dudley, Earl of Leicester with a steep redemption arc and an insatiable taste for revenge.

Haunted by his family’s ruin, Robert learned hard-earned lessons: how to gain power, how to hold it, and what it costs when you lose it.

But his Tower incarceration also taught Robert patience. Robert waited years to extract his revenge against the man who had aided Mary Tudor - John de Vere, Earl of Oxford – and not only against John, but also against his countess, Marjory Golding de Vere, and his three-year-old heir, Edward, the 17th Earl of Oxford. 

That vendetta - Robert’s subterfuge and repeated attempts to bring down Edward de Vere -lasted for 35 years. The test of wills between these two men is the hidden thread that, once pulled, releases a cascade of Elizabethan political, personal and literary secrets, including the most carefully guarded Tudor secret of all. Those stories are coming as we go deeper and deeper into who these fascinating Elizabethans really were!

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The next post will reveal the hidden figure who helped secure the Dudley brother’s freedom and introduce the two Dudley sisters who re-emerge as key players in Robert’s future.

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