Which of Queen Elizabeth I’s Favorites Died With the Most Debt? The Answer to a Tudor Puzzle
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Leicester, Warwick, Sidney and Hatton died broke. Edward de Vere and Elizabeth Trentham quietly beat the Tudor debt trap.
Robert Dudley, Earl of Leicester left behind obligations so large that his widow nearly drowned beneath them. Sir Christopher Hatton owed a fortune. Sir Philip Sidney’s debts devastated his young family. Ambrose Dudley, Earl of Warwick was more responsible than his brother, but still left a hefty negative balance sheet for his widow.
And Edward de Vere, Earl of Oxford? He died owing twenty pence.
That tiny figure, recorded in the official probate documents, overturns one of the most persistent myths about Oxford. Far from dying in financial ruin, he and his second wife, Elizabeth Trentham, appear to have devised one of the most sophisticated trust and estates strategies in Elizabethan England.
It turns out that Oxford was not a reckless spendthrift. He was a savvy financial strategist, and Elizabeth Trentham may have been the smartest woman in the room.
🫦 Queen Elizabeth I’s Favorites Ranked by Debt
Here’s the answer to the question posed in Which Elizabethan Court Favorite Died in the Most Debt? (A Tudor Puzzle), (modern equivalents calculated using the UK National Archives Currency Converter):
In first place: Sir Christopher Hatton died £70,000 in debt (about £9.6 million today), a staggering amount for a courtier who pined after Queen Elizabeth, but never married.
In second place: Robert Dudley, Earl of Leicester acknowledged that he did not know how much over £20,000 he owed, but after his death, records revealed that he left his widow Lettice, Countess of Leicester, with about £50,000 of debt (about £6.9 million today).
In third place: Sir Philip Sidney, Leicester’s nephew, who died £23,000 in debt (about £3.2 million today), which left his widow, Frances Walsingham Sidney, and their daughter practically destitute.
Fourth place goes to: Ambrose Dudley, Earl of Warwick, who died £7,000 in debt (about £1.0 million today), costly and embarrassing for his widow, Anne Russell Dudley.
Last place (and therefore, the greatest honor) goes to: Edward de Vere, Earl of Oxford, who died with 20 pence in debt, (£12, the price of a sandwich today), which his widow, Elizabeth Trentham de Vere, cheerily paid off.
Every one of these men spent lavishly to make a splash at court. But only Oxford successfully restructured his assets and his debts before he died. He made himself, his widow, his heir and his earldom legally untouchable. He employed legal structures that modern commercial real estate and trust and estates lawyers use today, but did not exist in Elizabethan England.
How do I know? Because I practiced commercial real estate law for decades. What Oxford did would make any modern commercial developer sit up and take notes. He also had a remarkable partner. But more on her in a moment.
😰 Why You Could Go Broke as a Tudor Courtier
First, let’s examine how the others failed.
While Sir Christopher Hatton (-£70,000) did not arrived at court with a pile of inherited lands, Queen Elizabeth showered him with income-producing assets and lucrative offices because of his services to the crown. Whether dancing a flawless galliard, serving as Queenly arm-candy at the drop of a feathered cap, or bleating piteously when her favor wandered elsewhere, Chris the Dish did her Majesty’s bidding to perfection. He also wasted a lot of money. Hatton built many fancy homes. He never even slept in one, a huge mansion called Holdenby, because her Majesty had never come to visit. He also never married and never had children, not even illegitimate ones.
Robert Dudley, Earl of Leicester (-£50,000), whose father and grandfather had lost everything due to treason [See: The Dudley Dynasty: Family Bonds Forged in Fire ], lived like a king thanks to the Queen’s favor and OPM (Other People’s Money). He not only spent on fortified castles, arms and ammunition, servants, golden cloaks, courtly entertainment, mistresses and jewels, he also financed an army of thugs and spies, and kept a few talented Italian poisoners on hand, in case anyone wanted to get even with him for what he’d done. Discretion costs.
Sir Philip Sidney (-£23,000). Debt ruined famous names as well. Sidney was poised to be very rich, standing to inherit both the earldoms of Leicester from his uncle Robert Dudley, and Warwick from his uncle Ambrose Dudley. At least that was the plan while neither of his uncles had a legitimate heir to those earldoms. But alas, Uncle Robert eventually did father a legitimate son, and alas again, Sidney died before Uncle Robert and Uncle Ambrose.
Ambrose Dudley, Earl of Warwick
(-£7000) managed to keep his expenses somewhat under control. Certainly compared to his brother, Ambrose looks fiscally responsible. Then again, Ambrose wasn’t trying to marry the Queen. Still £7000 of Tudor debt was a lot of money.
Even famous commoners succumbed to debt. Sir Francis Walsingham, [Elizabethan Spies and Plots: how Francis Walsingham Caught Ambassadors Plotting to Overthrow Queen Elizabeth I], long time government spy master, had to be buried “by dark, in Paul’s Church in London without any funeral solemnity” because he was “surcharged with debt.” Robert Devereaux, Earl of Essex, rescued Walsingham’s daughter, Frances, who had been married to Sidney and to Sidney’s debt. Gallant Essex not only put a countess’s coronet on Frances’ head, he suffered the Queen’s displeasure for it. In her Majesty’s opinion, Frances’ marrying Sidney had been fine, but Essex was above her station.
⚖️ The Myth vs. The Reality of the Earl of Oxford’s Finances
Yet, among these five favored men, only Edward de Vere, Earl of Oxford has gone down in history for mismanaging his finances and handed criticism for what has been assumed to be his financial ruin.
In fact, nothing could be further from the truth.
It is true that Edward de Vere, 17th Earl of Oxford inherited a financial disaster of an earldom when he reached his majority and was awarded his livery and his lands. Many men would have simply tried to keep up the charade of endless spending and pass the debt to the next generation. Oxford did not. Instead, he initiated a strategy to dig his way out of his inherited debt, beginning 30 years before he died.
Oxford rid himself of the financial burdens he had inherited with exceptionally skillful property management, and purposefully set up his financial profile to completely protect his widow and his heir.
Apparently, as a law student, he had been listening attentively in those real property classes at Gray’s Inn.
🪦 Oxford’s Inheritance Should Have Ruined Him
Only twelve when his father died, Oxford inherited his father’s earldom and a far flung portfolio of individual real properties, including manor houses, farms, abbeys, and forests. When he reached his majority, he and the Queen entered a two-year legal battle to settle how he was to pay off his father’s debt to the crown before he could take possession of any of those properties. By the late 1580s, with fines and penalties, that debt had grown to an astonishing £150,000 (about £21 million in modern terms).
During Oxford’s minority and wardship, her Majesty had entrusted management of the de Vere lands to (guess who?!) Leicester. Leicester neatly collected all the rents (OPM) and ran the de Vere lands into disrepair and ruin.
In short, at the age of 23, Edward de Vere was handed a portfolio of scattershot, rundown properties spread over half of England and a crushing debt that he had not created. But the sins of the fathers were inherited by wives and children in merry Old England.
What did Oxford do to address these two gigantic financial millstones around his neck?
Starting in his 20s, over the protestations of his first father-in-law, William Cecil, Lord Burghley, Oxford sold many of the underperforming, far-lung lands in his portfolio, and used the profits to pay off his debt to the crown and to buy a few high value and high rent producing properties near London. He traded up for fewer properties of higher value, located where he could keep an eye on them. And, this is key, he separated those new assets from himself and his earldom, once he found the perfect partner.
Not another nobleman. Not a lawyer. A woman.
🌹 Elizabeth Trentham: The Woman Who Changed Everything
Enter Elizabeth Trentham.
Elizabeth Trentham had learned how land made money from her commoner father in the Midlands. The Trenthams’ land ran to sheep and corn mills. Thomas Trentham left Elizabeth in possession of her own £1000 dowry, about £137,000 today, a respectable amount, but not nearly enough to tempt any one of the queen’s favorites looking for “an heiress”. He also left her something much more valuable: the right to choose her own husband. To understand how remarkable that was, compare Elizabeth’s freedom of choice with Mary de Vere’s, Oxford’s sister’s, struggles to choose her own husband:
Elizabeth Trentham served as the Queen’s maid of honor for ten years without misstep or scandal. She changed Oxford’s life. Their betrothal in July 1591 is exactly when a remarkable reshuffling of the Oxford earldom’s portfolio began.
You can learn more about Elizabeth Trentham here: Lasting Legacy and Love Amid Reputations Ruined: The Finale to 1591, the Infamous Year of Maidenly Scandal in Queen Elizabeth’s Court
Elizabeth understood something most men did not: owning investment property is not about prestige. It is about protecting cash flow and positioning for appreciation. Oxford not only found a way to legally sidestep the Tudor bankruptcy laws, he created what we would now recognize as an early form of land trusts, and transferred all his real properties into them. Those primitive land trusts were always titled in the name of his wife Elizabeth, and one male member of her family and one of his. Collectively, these “trustees”, not Oxford, held title to his earldom’s lands.
📜 A Tudor Asset-Protection Strategy
In plain terms, Edward de Vere, Earl of Oxford trusted Elizabeth Trentham with all his lands, assets and wealth, impoverishing himself personally and his earldom on purpose. The lands, the assets, the wealth remained, just titled in her name and the names of two male family members, different men for each property.
Why?
Married women could not own real property solely in their own names in Elizabethan England. Widows and heirs were responsible for the debts of dead husbands and fathers. Oxford also successfully and legally sidestepped the Tudor Statute of Fraudulent Conveyances (more details on that in the video linked below). Had Oxford and Elizabeth not structured the Oxford earldom as they did, upon his death, just like Lettice Dudley, Anne Dudley, and Frances Sidney, and Oxford’s own mother when his father died, Elizabeth and their son would have been hopelessly debt-ridden and vulnerable to creditors.
But because Oxford had transferred the assets in what we today call a form of “estate planning”, there were no assets and no income in the Oxford earldom when he died, nothing for creditors to seize.
✨ Twenty Pence and a Very Different Story
From £150,000 of debt to 20 pence of debt.
Think about that.
The 20 pence is so small, that it’s hard to know whether it was a rounding error or a deliberate “peppercorn” or nominal consideration, as it was then and is now known in legal parlance.
Why might that peppercorn of 20 pence have been deliberate?
To make clear that it was no mistake, that something of value would be given to the crown when Oxford died, and because Master of the Court of Wards at the time, was none other than his worst enemy, his former brother-in-law, Robert Cecil. Without the estate planning, Oxford’s heir would have become the ward of his nemesis. But with no income in the Oxford earldom, no one wanted Henry de Vere as their ward. No one that is except his mother, Elizabeth Trentham de Vere.
Burghley’s scolding letters calling Oxford a “spendthrift” have gone a long way towards mischaracterizing Oxford as an Elizabethan party boy with no sense of fiscal responsibility. But the historical record shows just the opposite is true.
Elizabeth Trentham and Oxford knew exactly what they were doing: in the right hands, debt can be converted to leverage.
🎥 If you want to learn many more details about how Elizabeth Trentham helped engineer one of the most elegant (and legal) financial escapes in Tudor England and meet the woman history has always underestimated, click here: Upholding and Raising the Most Honorable House: Elizabeth Trentham and What She Tells Us.
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