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50 Cunning Facts About Robert Dudley, The Dark Favorite

Dancy Mason

Of all the power-hungry men in Queen Elizabeth I’s court, Robert Dudley knew how to play the game of thrones best. This “Master Courtier” rose from utter ruin to the foot of the throne—and then into the queen’s bedchamber. But what happened behind those royal doors? Read on and find out.


Robert Dudley Facts

1. The Master Courtier

Dudley’s enemies accused him of being a “Master Courtier” who would stop at nothing to hold onto a shred of power. This dark reputation has followed him through the centuries, and even today Dudley is synonymous with a Machiavellian plotter. The real man, however, is both much darker and much more complicated than all that.

2. The Favorite: Tudor Edition

A notoriously handsome man, Robert Dudley was Elizabeth I’s “special” court favorite and, some say, the Virgin Queen’s one true love. With the power of his influence (and his loins) on the queen, Dudley all but ruled England for a time. But the bigger they are, the harder they fall—and the courtier’s spill was as spectacular as it was tragic.

3. The Eyes Have It

Queen Elizabeth I has a well-earned reputation for her cunning, shrewdness, and intellect, but all that seemed to go out the window when it came to sweet-faced Dudley. Aside from uncontrollable jealous rages (more on that later), she also showered him with pet names, the most famous being “Eyes,” for his handsome peepers.

4. We Go Way Back

Elizabeth and Dudley were actually childhood friends. Their families ran in the same circles, and they grew up alongside one another. But when they met again in adulthood, it was under much different circumstances.

5. Dudleys Do Right

On the surface, Dudley’s childhood seemed perfect. His parents had a happy family life and 13 children to prove it. Of their brood, Robert was particularly bright, and tutored under the likes of John Dee. The silver-tongued boy also showed a way with words that helped him curry favor wherever he went. Tragically, though, the Dudleys’ golden years were about to end.

6. Quickie Queen

Tudor-era court politics were no joke—and on July 6, 1533, they became positively fatal. That day, King Edward VI died childless, leaving an enormous power vacuum behind him. Everyone was struggling to back the right horse for the next monarch, with the Dudleys choosing Lady Jane Grey, AKA “The Nine-Days Queen.” So…need I say this went horrifically?

7. All in the Family

Robert Dudley led the charge for supporting Jane Grey, but he and his family barely had time to say, “Oops, my royal bad” before Elizabeth’s sister Queen Mary I swept in, won the conflict, and threw them all in the Tower of London. And I do mean all: Robert, his father, and his four brothers were all condemned do death. But that was just the beginning of the nightmare.

8. One Fell Swoop

While a chunk of her family were locked in the tower, Robert’s mother Jane Dudley worked tirelessly to get them released, even befriending people close to Queen Mary’s husband King Philip. In the end, she failed. Although she mercifully secured the safety of Robert and three of his siblings, his father and one brother went to the scaffold. There was just one upside to the terrible situation.

9. Fancy Seeing You Here

While locked in the Tower, Robert Dudley had a fateful cellmate: Princess Elizabeth. As Mary’s half-sister, Elizabeth was a contender for the still-vulnerable crown, and Mary wasn’t taking any chances. Given Robert and Elizabeth’s “close” relationship soon after, it’s easy to imagine the horrific experience bringing them together.

10. My Girl

In 1549, Dudley met the young, pretty Amy Robsart and was immediately smitten—for a time, anyway. She was the mere daughter of a local gentleman farmer, which wasn’t exactly the birth rank the Dudleys were aiming for. Robert didn’t care, and their wedding in 1550 was an unusual “love match.” Sadly, it was doomed to a heartbreaking end.

11. Tragedy Comes in Threes

Despite the Dudleys’ very rocky relationship with Queen Mary I, they eventually patched things up and returned to court…only to have yet more tragedy strike. In August 1557, Robert and his youngest brother Henry were fighting for King Philip at the Battle of St. Quentin in France. During the melee, Robert watched as his baby brother succumbed to cannon fire right in front of his eyes.

12. From Master of the House to Master of the Horse

Throughout all this turmoil—as well as his marriage to Amy—Robert and Elizabeth stayed very close, and Dudley soon reaped the benefits of their “friendship.” In 1558, Queen Mary died childless, turning Elizabeth into Queen Elizabeth I. The next day, Dudley became the powerful royal Master of the Horse…and his illicit courtship began in earnest.

13. Too Close for Comfort

Within months, it became very clear that Dudley was one of the most powerful men in the land, and had the ear of the queen on all matters of state. He likely had a lot else of her, too: His bedroom was right beside hers, and witnesses reported that “her majesty visits him in his chamber day and night.” This soon attracted the wrong kind of attention.

14. Royal Enemy Number One

Queen Elizabeth was obviously the most eligible bachelorette in the country, and her courtiers and advisors did not take well to her fixation on the married Dudley. Many of them conspired in plots against his life, so much so that Dudley took to wearing chain mail under his clothing. As for Dudley’s loving wife? Well…

15. You Can’t Sit With Me

Elizabeth was a notoriously possessive woman, and her green-eyed monster was alive and well even at the beginning of her relationship with Dudley. While Elizabeth showered Dudley with well-appointed chambers, she refused to entertain Amy Robsart, who spent most of her time outside of London and away from her husband. And poor Amy had it even worse than that.

16. A Malady for Milady

Just as Queen Elizabeth was setting up Dudley’s rooms next to hers, scandalous news ripped through the palace. Dudley’s wife was suffering from an illness in her breast—most historians believe it was breast cancer—and was close to death. According to the whispers, Dudley wouldn’t have long to wait before he was a free agent. But then something even darker happened.

17. Fall From Grace

On September 8, 1560, Dudley’s wife Amy Robsart was found dead in her residence at the bottom of a flight of stairs. According to Dudley himself, he was in total shock over the news, writing, “The greatness and the suddenness of the misfortune doth so perplex me.” Yet those closest to the queen had a much different interpretation of the incident…

18. Pointing Fingers

According to many in Elizabeth’s court, Amy’s tragic end was all Dudley’s doing. Unable to wait any longer for her to pass from cancer, suspicious courtiers claimed that the Lord offed his Lady quickly and simply with a “fall” down the stairs instead. Modern historians, however, have a more disturbing suggestion.

19. A Twist of Fate

Some experts suggest that Robsart’s cancer may still have been the culprit. Though the stairs didn’t seem too dangerous, the cancer could have metastasized into her spine, allowing her neck to crack under the slightest pressure. At the time, investigators also ruled Robsart’s fall as an accident…but Dudley was still in hot water.

20. Thoroughly Modern Dudley

Dudley may have been pretty, but he wasn’t afraid to get down and dirty. He took his palace duties seriously, particularly Tudor England’s nasty plumbing problem. After dealing with the castle’s sanitary issues for years, he even hired someone to finally build Elizabeth a water closet, AKA a toilet. A clean queen prevents a mean queen.

21. All My Children

Throughout their entire relationship, persistent whispers claimed that Elizabeth had secret children by Dudley. This wasn’t just the idle gossip of commoners or country nobility, either—even those in Elizabeth’s own court believed it was possible. Many today think this is just speculation, but one scandalous incident says otherwise…

22. Born Into Sin

Allegedly, in 1587, a man calling himself Arthur Dudley emerged and claimed he was Robert and Elizabeth’s natural son. His evidence was stunning. According to Arthur, he was conceived in 1561, exactly the time that Queen Elizabeth had been bed-ridden with a mysterious “swelling” illness. Coincidence or conspiracy?

23. Undercover Lover

Robsart’s tragic accident seemed to dash all Dudley’s hopes of a royal marriage, but Elizabeth refused to give him up. She would often disguise herself as a lady-in-waiting just to catch a glimpse of him, and kept encouraging his suit. Meanwhile, her courtiers worked overtime to keep Dudley from the crown. Then these courtly games hit a bizarre climax.

24. Three’s Company

In 1563, Queen Elizabeth pulled the ultimate “we’re totally chill” move and suggested Dudley marry her cousin Mary, Queen of Scots instead. If the politically advantageous marriage went through, Liz wanted the three of them to live at the English court in an awkward ménage a trois, all so she’d never have to give up her favorite. There was just one problem.

25. A Marriage of Convenience

Mary was understandably skeptical about the man-meat her cousin had sent to her on a platter, and her first response was actually to ask Elizabeth if she was serious. The Queen assured Mary she was, and that if she went through with it, she’d be named heir to England. Satisfied, the power-hunger Mary agreed—until Dudley threw an enormous wrench into the proceedings.

26. Well, I Don’t

For one of the first times in his life, Dudley disobeyed his queen and staunchly refused to wed Mary. He spent the entire exchange passively sulking about it, all while desperately trying to find Mary another groom. When he landed on Henry Stuart, Mary’s actual future husband, all bets were off and the deal fell through. It was the first crack in Robert and Elizabeth’s relationship, but there were more on the horizon.

27. If I Can’t Have You, No One Else Can

Dudley and Elizabeth’s love was truly twisted, and pretty much the definition of toxic. Though Elizabeth wouldn’t marry him, she refused to consider anyone else, and Dudley himself only thought about marrying someone else with “great repugnance.” He also frequently sabotaged the suits of her other royal hopefuls. However, that doesn’t mean Dudley didn’t have sidepieces…

28. Secret Sidepiece

Dudley’s most long-term and serious affair outside of Elizabeth was with the beautiful Douglas Sheffield, a widowed woman at court. Still, they both knew the score: Dudley told her point-blank that he could never marry her or give her an heir, and he even offered his services in finding her a husband. Not all things, however, go to plan…

29. Who’s Your Daddy?

In 1574, Sheffield got pregnant with Dudley’s son, the future Robert Dudley, Jr. True to his word, Dudley never acknowledged the boy as legitimate, though he did help care for him. It was the most he could do; to acknowledge a child and a relationship outside of his dalliance with Elizabeth would, in his words, lead to his “utter overthrow.”

30. A Promise Is a Promise

In the end, Dudley shouldn’t have been so surprised that Elizabeth didn’t want to lock it down with him. He once recalled an eight-year-old Elizabeth telling him during a childhood conversation that she would never marry. Then again, the adult Elizabeth kept assuring him if she did marry an Englishman, it would be him. Uh, thanks, I guess?

31. Joined at the Hip

Elizabeth was incredibly controlling about where Dudley went and when he did it. She refused him from taking far-away appointments and everyone at court feared her moods when he did happen to be out of the capital. When Dudley went away for a mere few weeks in 1578, he got an urgent “come home” message from a courtier saying, “This court wanteth your presence. Her majesty is unaccompanied.” Is it any surprise that Dudley eventually had enough?

32. Strictly Ballroom

Besides his administrative duties as Master of the Horse and later as Lord Steward, Robert Dudley also had to take on ceremonial duties. He was basically an event planner for many of Elizabeth’s parties, as well as her official dance partner once those balls got off the ground. Man, sure hope he was an extrovert.

33. Party on, Rob

In July 1575, Dudley threw an enormous 19-day bash at his home in Kenilworth Castle, complete with fireworks, masques, and bear-baiting. But Dudley had a manipulative agenda. He also used the party as a “Love me or leave me” message to Elizabeth, basically bidding for her hand for the last time. It didn’t work.

34. Kissing Cousins

Douglas Sheffield wasn’t Dudley’s only mistress—Elizabeth actually had stiffer competition in her cousin Lettice Knollys. Robert and Lettice had started a flirtation back in 1565, causing Elizabeth to erupt with jealousy. She had good reason: Lettice wasn’t just one of the most attractive women in court, the pair also shared an uncanny family resemblance, right down to their red hair. And this wasn’t the only scandal.

35. When the Husband’s Away

When Dudley first met Lettice, she was already married to the Earl of Essex. To the court’s great titillation, this didn’t stop them. When the Earl went away to Ireland in 1573, Lettice and Dudley jumped on the opportunity and likely started a full-blown affair. When the day of the Earl’s return approached, people started gunning for a fight between the two men—but something else happened entirely.

36. Whatever Robert Wants, Robert Gets

When Lettice’s husband the Earl of Essex came back from Ireland in 1575, he promptly died of dysentery. Dudley’s lover was suddenly a free agent, but instead of celebration, he only got yet more scandal. People at court began to whisper that the “Master Courtier” was at it again. First, he offed his wife, and now he must have poisoned his mistress’ man. Dudley’s next move didn’t help matters.

37. Love in the Shadows

In September 1578, Dudley did the unthinkable: He married Lettice Knollys in a secret ceremony, with only a select number of friends and family in attendance. Knowing it would break Queen Elizabeth’s heart, Dudley kept the nuptials from her as long as he could. When Elizabeth finally found out, her response was utterly disturbing.

38. And Don’t Come Back

Elizabeth was apoplectic when, months after the fact, she discovered Dudley was a married man. She also made sure Lettice felt her wrath: the queen banished her cousin from court, seriously cutting off Knollys’ social life. For years after, the queen kept tabs on any travels Lettice made, particularly if they were with her husband. Yet what Elizabeth did to Dudley was even more spiteful.

39. Royal Refusal

Elizabeth never accepted Dudley’s marriage. For almost a decade after, she publicly humiliated him whenever she could, sneering in front of members of the court that Lettice was a “She-wolf” and Dudley a “traitor” and “cuckold.” At the same time, she still insisted on keeping Dudley near her whenever she could. For Dudley, this was the beginning of the end.

40. Setting Son

After he fell out of favor—at least partially—from Elizabeth, Dudley’s life seemed cursed. In 1581, Lettice fell pregnant, and the happy couple had a baby boy, also named Robert. Then the poor child suffered a terrible fate. In 1584, when he was just three years old, little Robert died very suddenly. Dudley and Lettice’s reaction was the definition of tragic.

41. Mental Health Day

Dudley had been an attentive and sensitive father, and the couple was emotionally devastated when their son passed. Dudley even refused to complete his court duties for weeks after the tragedy, staying home “to comfort my sorrowful wife for the loss of my little son.” Dudley had waited years for Elizabeth to marry him, denying himself an heir for decades, and now that heir was gone.

42. The Lord Collector

The Elizabethan Era is considered one of the greatest periods for culture, with giants like Shakespeare performing plays during her reign. However, we may have Dudley to thank for this more than we do Elizabeth. While the queen wasn’t a huge fan, Dudley was deeply involved in the arts. He was one of the first private collectors of paintings, and corresponded with many creative greats of his day like Edmund Spenser and Philip Sidney.

43. Warrior Lord

Dudley wasn’t just a poncy court favorite. As a young man, he fought in many rebellions, and his biggest claim to fame was his participation in the legendary English battle with the Spanish Armada. In fact, when Elizabeth gave her famous speech to her troops, Dudley was walking right beside her horse. Little did they know, it would be one of their last glorious moments together.

44. The Queen and I

In the aftermath of England’s famous victory over the Spanish Armada, Dudley was riding a high with Elizabeth once more, and re-entered London from the battlefield “as if he were a king.” For the next few weeks, he received the rare privilege (even for him) of dining with the queen almost every day. Then it all came to a crashing halt.

45. The End of an Era

On September 4, 1588, Dudley finally met his fate. The queen’s favorite suddenly collapsed and died in Cornbury Park near Oxford at the age of 56. No one around him had expected it—but the dark signs were there.

46. Fatal Culprit

Dudley’s health had actually been failing for some time before this, and he fatigued easily. Today, historians suggest that Dudley may have passed from either stomach cancer or malaria. Not that this comforted Elizabeth when she found out the horrific news…

47. Stop the World

Upon hearing that Dudley had suddenly passed, Queen Elizabeth I was utterly inconsolable. She shut herself in her chambers for days on end and refused to see anyone. It got so bad that one of her advisors even had to break the door down and extract the Queen of England from her mourning so she could run the country.

48. Together Again

Dudley lived the cunning life of a courtier, but his last wishes were heartbreaking. Upon his request, his family buried him alongside “the noble Impe,” his little son Robert who had died at the age of three. When Lettice Knollys passed years later, she too chose to be buried beside them, even though she had re-married.

49. To My Own True Love

Queen Elizabeth lived more than a decade after losing her favorite, but she never forgot Dudley. When she finally passed, her advisors searched her belongings and found a letter inside her bedside table. Its contents were heartbreaking. It was a letter from Dudley dated just before he died, where he ended “I humbly kiss your foot… by Your Majesty’s most faithful and obedient servant.” She had even marked it as “his last letter” to her.

50. I Did It My Way

Historians today have come to an incredibly grim conclusion in the death of Dudley’s first wife, Amy. They maintain there wasn’t foul play involved, yet it was still a strange fall that shouldn’t have necessarily been fatal. This has led some experts to suggest suicide. After all, Robsart knew her end was coming one way or another, and she might have chosen to go on her own terms. And there is one more possibility.

Sources: 1, 2, 3, 4


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