Tragic Facts About Anne Boleyn, King Henry VIII’s Doomed Queen

Rachel Seigel

Anne Boleyn is one of the most infamous and tragic queens in history—and for good reason. Her courtship of King Henry VIII turned into the scandal of the century, with English law changing literally under her well-shod feet. But once Anne actually succeeded in becoming consort, her naughty fairy tale transformed into a vicious nightmare. One she would never make out alive.


Anne Boleyn Facts

1. She Came From A Powerful Family

In many ways, Anne Boleyn was born to be great. Her father Thomas Boleyn was a court favorite of the old King Henry VII, and the Boleyns were one of Britain’s top families at the time. Indeed, her father was constantly going on diplomatic missions all around Europe as she grew up—and this led Anne to one big date with destiny.

2. She Had A Cunning Mentor

When Anne was just 12 years old, her father’s power paid off in a big way. Margaret of Austria, the daughter of the Holy Roman Emperor, did the Boleyns a solid and invited Anne to join her in her court. She wasn’t disappointed: Margaret was soon affectionately calling Anne her “little Boleyn” and taking her everywhere. It was a big step up for the girl, but her next step brought her right next to Henry VIII.

3. She Was Friends With Henry VIII’s Sister

In 1513, Anne took up a position as maid of honor to Queen Mary of FranceThis was crucial for one simple reason. Queen Mary was none other than Henry VIII’s sister, and Anne was moving closer and closer to his inner circle. With Mary’s help, Anne stayed in France for nearly seven years, soaking in its cosmopolitan culture and turning herself into a refined young woman.

When she emerged and returned to England, courtiers couldn’t believe their eyes.

4. She Had A Je Ne Sais Quois

French culture at the time was so liberal it was almost scandalous, and Anne Boleyn had certainly taken notes. The English were agog at how exotic and seductive the young woman had become, praising the way she moved right down to the way she dressed. In particular, Anne favored the sleeker “French hood” as a head covering instead of the more matronly English “gable” hoods. But that was far from all.

5. She Was A Coquette

The coquettish Anne had spent her time in France studying languages, dancing, and literature, but she had one particularly scandalous skill. The French were masters of “courtly love”—elaborate and flirtatious games designed to both keep men at arm’s length and get them all hot and bothered underneath their britches. And Anne? Was a champion at this. Even so, she had other ways of getting what she wanted.

6. She Was More Than A Pretty Face

According to almost everyone who met her, Anne Boleyn was excruciatingly attractive. Slim and dark with long black hair and brown eyes, men thought she was utterly captivating—but not just for her looks alone. Her friends knew her as a lively, quick-witted, and charming girl who was often the smartest person in the room. Yet underneath that perfect facade, Boleyn was hiding something.

7. She Was A Wolf In Sheep’s Clothing

For all that she was vivacious and magnetic, Boleyn hid a little-known dark side. Beneath her jovial attitude, she was moody, sharp-tongued, and extremely quick to anger when she didn’t get what she wanted. At one point during an argument with her uncle, she reportedly spoke to him with words that “shouldn’t be used to a dog.” Ouch.

Soon enough, this temper got her into deep trouble with Henry VIII. But for now, she was getting into an entirely different kind of mess.

8. Her Father Tried To Force Her Into Marriage

Anne’s road to King Henry VIII was dangerous, and her first snag was a major one: She was supposed to marry someone else. As soon as she’d gotten back to England from France, her father began angling for her to marry her much-older cousin, James Butler. It would have been a strictly political union, and quite likely utterly loveless.

Thankfully for Anne, then, negotiations halted before she became a kissing cousin. But much more scandalous opportunities were arising.

9. She Had A Sibling Rivalry

While Anne was off trying to resist her cousin’s advances, her older sister Mary Boleyn was making quite a splash in King Henry’s court—and proving herself to be quite the rival to Anne’s beauty. Case in point: Although Henry was currently married to Catherine of Aragon, he quickly took Anne’s sister on as his mistress. Um, ew. But it gets even grosser.

10. Her Mother May Have Been Her Competition

There were persistent rumors at the time that Henry had bedded not just Mary, but also the Boleyn matriarch, Lady Elizabeth Howard. When accused of this one, Henry protested, “Never with the mother,” which still pretty much confirms his penchant for the Boleyn girls. Whatever the truth, Anne took one look at her sister’s antics and decided she wanted to go to court, too. Only, it didn’t go the way you think it would. 

11. She Had A Seductive Talent

When Anne got to Henry’s court, she brought a secret weapon with her: Her incredible dancing ability. Indeed, she became famous for her dancing, and no courtier seemed to be able to look away. “Here,” one of her admirers wrote jubilantly, “was [a] fresh young damsel, that could trip and go.” As it happened, this is exactly how she caught Henry’s attention.

12. She Got A Notorious “Staircase Moment”

Anne used Mary’s high place in the king’s bedroom to her full advantage. Soon, she made a jaw-dropping debut. On March 4, 1522, she danced with her sister at a public fete at the royal palace. During the performance, Boleyn vibrated with magnetic new-girl energy, and we still have records of how resplendent she looked in a white and gold gown. Except this attracted the wrong kind of attention.

13. She Snubbed The King

The beautiful Anne got scads of male admirers after her legendary dance, King Henry included. After all, the king’s fling with Mary Boleyn was winding down, and he had a taste for the fresh meat coming from his favorite family. Which is when Anne dealt the king a legendary snub. She didn’t go after him. Oh no, she had a much different suitor in mind.

14. She Had A Secret Lover

At the time, Anne much preferred one of her other suitors at court, the dashing Henry Percy, who was the heir to the Earl of Northumberland. Boleyn poured all of her energy into capturing Percy’s heart, not the king’s, and the pair had an intense romance together over the next days and weeks. In fact, Anne was so in love with Percy, she made a drastic decision.

15. She Was The “Other Woman”

After longing gazes and letter-writing, Anne and her beau Percy couldn’t wait anymore and got engaged in secret. And sure, that sounds extra romantic and intimate, but there was a disturbing reason for their secrecy. You see, Percy was already formally engaged to an entirely different woman. As it happened, though, that was the least of Anne’s problems.

16. She Was In A Star-Crossed Romance

Anne and Percy were dumb and in love, but nobody else was on their side. Percy’s father absolutely refused to support the match, and the young couple also failed to get any marital backing from Cardinal Wolsey, who was an important figure at court. In other words: They were royally screwed. Beaten down, they eventually had to give each other up and went their separate ways.

It was a gut-wrenching demise for their young love—yet there might have been an even darker cause underneath the split.

17. She Made A Formidable Enemy

Some historians suggest that even this early on, King Henry had a serious eye on the other Boleyn girl. Jealous of the attention Anne was getting from (and giving to) Percy, the king may have personally put the kibosh on their relationship, ordering Cardinal Wolsey to forbid their marriage on pain of royal punishment. Then again, there was yet another serious obstacle.

18. She Was A Snake In The Garden

When Anne came to the English court, she took a place in the household of Henry’s queen, Catherine of Aragon. Yeah, sleeping with your boss’s husband is never a good look, and maybe that’s part of why Anne kept Henry at bay at the beginning of their acquaintance. Nonetheless, once Percy was out of the way, Henry really began his wooing.

19. She Played Mind Games

With his rival down and out, King Henry started pursuing Boleyn in earnest in 1526. His tactics came on strong. Besides heartily engaging in games of courtly love with the expert Anne, he also wrote her extravagant love letters complete with lavish presents to remind her of his affections. But his first gift to her was extremely telling.

20. She Got A Selfish Gift

Over their courtship, Henry often sent over precious gemstones like pearls and rubies to Anne—as long as he could stash them away from his wife Catherine, of course—but his initial gift really takes the cake. His very first letter included an elegant gold bracelet…that was set with his own portrait. Maybe this narcissism turned Anne off, because she sure didn’t react well.

21. She Played Hard To Get

While Henry was throwing every trick in the book at Anne, she…was still not interested. In fact, Anne specifically refused to bed him. And even when Henry promised he’d promote her from a regular side piece to his chief mistress, she still turned him down. Anne’s rejection of one of the most powerful men in Europe might seem bizarre…until you dig a little deeper.

22. She Was On The Rebound

To this day, historians debate about what spooked Anne when it came to warming Henry’s bed. One explanation is nothing short of heartbreaking. Fresh off her breakup with Henry Percy, some claim Anne was simply nursing her wounds and wanted the pesky royal to leave her alone. Others, however, have a much different—and more ruthless—suggestion.

23. She Played The Long Game

Although Anne may have indeed been hung up over Percy, some believe her refusals had nothing to do with this. Instead, she was simply playing the long game. Anne wanted to be much more than a mere “mistress”—she wanted Henry to annul his marriage to Catherine of Aragon and make her queen. And the more hot and bothered Henry was, the more he’d be putty in her hands.

Except before that happened, Henry dealt Anne a cruel blow.

24. She Contracted A Terrifying Disease

In 1528, Henry and Anne almost lost everything they were working towards. That year, Anne nearly perished from the mysterious sweating sickness, whose causes are still unknown. The terrifying ailment could rapidly destroy an otherwise young and healthy victim—and when Henry suspected Boleyn had it, his response was utterly heartless. 

25. Henry Abandoned Her

Henry VIII was an infamous germaphobe, and he was particularly terrified of the sweating sickness. So when one of Anne’s ladies contracted it and passed it on to Anne, the king didn’t want to nurse his lover back to health. Nope, he wanted her as far away from him as possible. Henry immediately sent her back home to Kent to “recover” and get the heck out of his court.

When she survived, however, Henry seemed all the more determined to make her his queen. Then again, he had some big ulterior motives.

26. She Had Great Timing

As it turned out, Anne’s timing in courting Henry was impeccable. When she arrived on the scene, Henry’s marriage was majorly on the rocks. For one, although Queen Catherine had given birth to Princess Mary, AKA “Bloody Mary,” the aging woman hadn’t given Henry his much-coveted male heir.  But there was an even bigger issue—one Anne would take full advantage of.

27. She Drove Henry To Distraction

With Anne denying him in the bedroom, King Henry began to get deranged ideas. He decided that since Queen Catherine had been briefly married to his older brother Prince Arthur before the prince died, God was mad at him for stealing his brother’s wife. Very logically, this was why he didn’t have a son. And while Catherine swore she never consummated the union, it was no good. Henry began angling for an annulment, which was the only way the Catholic Church would condone him re-marrying Anne.

Yes, King Henry was walking, talking, giant RED FLAG. But Anne’s response to all this was…pretty gross, honestly.

28. She Got An Indecent Proposal

When Henry started talking about chucking Catherine out the door, Anne was thrilled. Although she still kept Henry away from her bed (yes, this girl was smart), she happily accepted his proposal of marriage. And while he was, you know, already married, the lovebirds assumed it would be the snap of a finger to oust Queen Catherine. This very infamously did NOT end well.

29. She Was A Bully

Of course, we know now that Henry’s annulment was no easy feat. But few know Anne’s dark role in the proceedings.  Tag-teaming with Henry, she began campaigning Cardinal Wolsey—the same man who’d nixed her wedding to Henry Percy—to support her new romantic ambitions. And when Wolsey couldn’t convince the Church to annul the royal union, Anne’s wrath was bone-chilling.

30. She All But Killed A Man

In the beginning, Anne played sweet at the English court, hiding the same infamous temper she’d always had. Well, now she hit the roof. Aghast at Wolsey’s failure, she turned on him like a rabid dog. Within months, she had a direct hand in getting him charged with high treason, and the stressed and aging Cardinal died soon after.

Still, this revenge wasn’t enough for Anne. She had tasted power, and she soon came back for more.

31. She Was Power-Hungry

Anne toiled on the sidelines with Henry for years, but that didn’t mean she was a wallflower. As time went on, she inserted herself more and more into a ruling role, once using her charms to broker an alliance with France. In 1532, Henry even made her the Marchioness of Pembroke, a rank that placed her above all her fellow courtiers. But as Anne rose in power, her desperation deepened.

32. She Tried To Mean-Girl The Queen

Throughout all of Henry and Anne’s machinations, Catherine of Aragon remained staunch in her conviction that she was the one true Queen of England. In response, the illicit couple made her pay for it. The King and his mistress wheedled at Catherine constantly to get the heck out, with Henry once cheerily suggesting Catherine join a convent. Catherine’s legendary response? “God never called me to a nunnery. I am the King’s true and legitimate wife.”

With that avenue shut down real quick, Henry and Anne turned to much crueler measures.

33. She Was A Usurper

In 1531, Anne achieved a stunningly heartless victory. That summer, Henry literally abandoned his wife, moving his court without telling Catherine or his daughter Mary. In a letter, Catherine complained that Henry didn’t even wake her up to say goodbye, presumably because he was too busy with Anne Boleyn. And then the couple twisted the knife in.

34. She Stole Catherine’s Bedroom

In another show of his (supposedly) undying devotion to Anne, Henry forbid Catherine from stepping foot in his new court…and in the meantime, gave her royal chambers to Anne Boleyn. Ouch. Catherine later said of the trials, “It is enough to shorten ten lives, much more mine.” Yet just as Anne came so close to what she wanted, it all backfired on her.

35. The Public Hated Her

Surprising exactly zero people, the public did not take well to the idea of Anne becoming Queen. After all, the common crowds absolutely adored Catherine and (somewhat justifiably) blamed Boleyn for splitting apart the marriage. As Anne cemented her position, the grumblings only got louder, with people calling her cruel names and accusing her of beguiling Henry with witchcraft. It climaxed with a terrifying event.

36. She Had To Flee For Her Life

One evening after Anne dined near the Thames river, she got the shock of her life. As she was heading outside, a mob of angry women attacked Boleyn, convinced she was bringing their king and country to ruin. A terrified Anne had to make a narrow escape on a boat to save herself from their wrath. It was all finally at a fever pitch…until King Henry made a fateful decision.

37. She Broke Down The Catholic Church

Henry and Anne’s difficulty in securing an annulment was so drawn out, people began calling it “The King’s Great Matter.” Finally, after seven long years of fighting with the Church, Henry had quite enough—and the king’s actions changed history. He infamously split from Roman Catholicism entirely and installed himself as the head of the brand new Anglican Church.

With no more middlemen, Henry pushed through a new-fangled “divorce” from Catherine of Aragon. Anne and Henry had finally gotten what they wanted, and they moved fast.

38. She Had A Secret Wedding

In 1533, it finally happened: After many machinations and even more years, Anne Boleyn became Queen Consort of England, marrying Henry on January 25. But there was one thing about the union no one knew. The power couple had already married each other in a super-secret ceremony the previous November. And that wasn’t all.

39. She Finally Gave In To Henry’s Demands

Since their covert wedding, Anne had very much let Henry into her bedroom. So much so that when Anne had her formal ceremony that January, she was already pregnant with Henry’s child. Still, Anne was certainly not leaning into the “wife and mother” roles. Oh no, she had much bigger plans for herself. Plans that involved more revenge.

40. She Had An Extravagant Coronation

No one was extra like Anne Boleyn was extra, and she made darn sure her coronation day outdid Catherine’s. Starting on June 1, 1533, the event lasted four glorious days, with Anne wearing a series of covetable outfits the entire time. On the last day, Anne one-upped herself and wore an unforgettable gown dyed royal purple and topped with ermine. Then she got a final cut in.

41. She Had A Cruel Motto

Everybody knew Anne had a rather twisted and droll sense of humor, and once she was queen she put it on full display. In reaction to the many vehement protests against King Henry choosing her as his queen, she temporarily took the phrase “Ainsi sera, groigne qui groigne,” as her motto, which translates into “Grumble all you like, this is how it’s going to be.” 

Anne was pregnant, Queen of England, and more powerful and smug than she had ever been. In other words: There was nowhere to go but down.

42. She Was Desperate For A Boy

After her coronation, Anne settled into royal life and prepared to give King Henry his long-desired son. And indeed, all signs pointed to a boy. Almost all of the king’s astrologers said the stars mapped out a male heir, and Anne and Henry were also confident they were about to welcome a son. Instead, Anne was entering into a horrible nightmare.

43. Her Daughter Was Iconic

In September 1533, Anne gave birth to a healthy child—but not to a boy. She had a little girl, the future Queen Elizabeth I, and the shock sent both the royal couple into a tailspin. Henry canceled his celebratory “It’s A Boy!” jousting match, and royal scribes hastily changed “prince” to “princess” in their official announcement. Anne didn’t know it then, but it was the beginning of the end.

44. She Was In A Dysfunctional Relationship

Henry and Anne were both hotheads, and their relationship was already extremely volatile—one man characterized it as “storm followed sunshine, sunshine followed storm.” So when Anne didn’t immediately give Henry a male heir, the king’s patience with his testy wife went right down the drain. He began to resent her sharp intelligence and her even sharper tongue, demanding that she submit to him as his wife, not as his equal. It threw Anne into a feverish act.

45. She Suffered A Mother’s Worst Nightmare

For the next three years, Anne turned the phrase “try, try again” into a backbreaking, Herculean effort. She was likely pregnant another two times after having Elizabeth, but tragically suffered through miscarriages each time. All the while, Henry grew ever more distant, and ever more regretful that he’d married her in the first place. By 1836, she was on thin ice—and then her Hail Mary came.

46. She Tried To Save Herself

In early 1536, Anne was pregnant again and more sure than ever that she was going to deliver Henry a healthy boy and cement her position as his consort. She did everything by the book, taking care of her body and staying away from stressful situations, all to ensure she would never have a miscarriage again. And then, suddenly, a grisly event brought Henry back to her.

47. She Got A Petty Revenge

In January 1536, King Henry and Queen Anne got word that Henry’s ex-wife Catherine of Aragon had died. Their reaction was so disturbing, it’s impossible to forget. The royal couple was so overjoyed at the news, the next day they even dressed up in jubilant yellow clothing to “celebrate” the macabre occasion. If they knew the truth of Catherine’s end, though, they might have thought twice.

48. People Thought She Killed Her Rival

When Catherine of Aragon passed, doctors opened her body to find that her heart had turned completely black. This was bad news for Anne. Suddenly, the court began to whisper that Boleyn had poisoned the former queen just to get her out of the way. While we now know that Catherine had cancer of the heart, it did nothing to strengthen Anne’s PR at the time. But by then, there were even darker problems at play. 

49. She Met Her New Competition

King Henry always had a wandering eye, and when his marriage to Anne started fraying, he turned his attentions elsewhere. Namely, to the pretty, sweet, and comparatively submissive Jane Seymour, who would eventually become his third wife. Oh, and here’s an icky detail: Seymour was also Boleyn’s second cousin. Sure, Anne still had her pregnancy as the ace up her sleeve…but it was all about to come crashing down.

50. Her Cousin Betrayed Her

Despite their family ties, Anne Boleyn and Jane Seymour weren’t exactly close. More than that, Anne Boleyn was no dummy: She knew that a relationship was growing between Henry and Jane under her nose. In fact, she probably had proof of the fact. In one incident, Boleyn discovered that Henry had given Jane his picture to wear in a locket around her neck, just like the bracelet he had once gifted her. Then it started to get really messy.

51. She Got Into A Cat Fight

Jane Seymour might have looked docile on the outside, but historical evidence suggests she, like Anne, was anything but. According to one account, one day at court Jane began brazenly opening and shutting the offending locket right in front of Anne. Once she realized what was going on, Boleyn furiously tore the chain so violently that she cut her fingers open. Only, Jane wasn’t done shoving the affair into Anne’s face.

52. She Threw A Temper Tantrum

One evening, Anne walked into a room only to find the treasonous Jane sitting prettily on her husband’s lap. Anne’s response went down in infamy. Giving in to her notorious temper, Anne reportedly flew into a very public rage at the sight of Jane Seymour lounging atop King Henry VIII. Anne was already on edge, and she had another shock coming.

53. She Watched Her Husband Nearly Die

Around this time, King Henry VIII participated in a jousting tournament, with Anne watching on from the sidelines. However, this only meant she had a front-row seat to a horror show. In front of her eyes, an opponent unhorsed Henry with such force, the king was unconscious for a good two hours. In the end, all this stress was too much for Anne, and the consequences were devastating.

54. She Lost Her Baby

In between watching another woman straddle her husband and watching her husband slip into a semi-coma, Anne’s mental health took a nosedive, and her physical health followed. Just five days after Henry’s disastrous tournament, Anne miscarried yet again, losing the child she was so desperate to give Henry. But that’s not even the most harrowing part.

55. She Had A Brutal Fall From Grace

When the attendants looked at the infant Anne had just miscarried, they saw it was a boy. And even though Henry had helped cause the drama, he now blamed Boleyn entirely for the miscarriage. When imperial ambassador Eustace Chapuys heard the news, he apparently intoned that Anne “has miscarried of her savior.” He was all too right.

56. Henry Iced Her Out

When King Henry VIII turned on Anne at last, his spite was swift and brutal. After all, he had spent an agonizing near-decade splitting from Catherine of Aragon, and he had no intention of doing the same with Anne. Within months of losing their infant son, Henry was already plotting to marry Jane Seymour. But this time, his punishment was so much worse than divorce.

57. The King Sabotaged Her

Henry’s plan of attack started with a series of abhorrent snubs to Anne. While his poor queen recovered from her traumatic miscarriage, Henry started telling people Anne had indeed “bewitched” him into marrying her. Not stopping there, he also refused to give Anne’s brother George the prestigious Order of the Garter. And then he turned to public humiliation.

58. Henry Replaced Her

People say “they go the same way that they came,” and nothing could be truer when it came to Henry. In fact, he pulled the exact same move on Anne that he had for Catherine. Within days of losing his narcissistic love for Anne, Henry had installed Jane in the royal quarters. With this done, Henry worked on the bloodiest phase of his plan.

Queen Elizabeth I.

59. The King Accused Her Of Horrific Acts

By the end of that April, Henry initiated some seriously sinister moves on Anne’s friends and family. The king detained and questioned a series of male courtiers who knew Anne, accusing many of them of sleeping with his witchy wife. Chillingly, Henry even took in Anne’s brother George, accusing him of having romantic relations with his own sister. Yes, Henry was off the deep end, and it wasn’t going to get better.

60. She Was “Treasonous”

In early May, Henry pulled the trigger on his malevolent plot. He arrested his wife for high treason—it being treasonous for a queen to sleep with anyone but her king—and threw her into the infamous Tower of London to await her fate. Upon her detainment, Anne apparently collapsed from the shock. But when she recovered, she made a genius chess move.

61. She Knew How To Manage Her Image

Right after Henry’s men told her of the charges, Boleyn went back to her rooms and got changed into an exquisite crimson velvet dress. This wasn’t just Boleyn’s vanity talking, either. Anne wanted to make sure that when the men led her to the Tower, she looked every part the queen, showing Henry exactly what he was going to be missing. Still, none of this saved her from her utterly tragic fate.

62. She Went On Trial

In mid-May, King Henry finally put Anne on trial. While she stood there—with her brother George suffering through a similar trial on the same day—the Crown accused her of everything from witchcraft to plotting Henry’s death so she could remarry. By then, it was far too late for rebuttals. A jury of 27 people found Anne guilty on all counts and condemned her (and George) to execution. But one detail from her trial is gut-wrenching.

63. Her Ex-Lover Condemned Her

As Anne looked into the jury’s eyes, she saw a familiar face. That of Henry Percy, her old love and the man she tried to marry all those years ago. You know, before King Henry pulled her into his destructive orbit. Even more disturbingly, the jury’s decision was unanimous, which meant Percy had personally sent his old flame to the block. And it gets more soap opera than that.

64. She Was In A Romeo And Juliet Romance

It might be easy for us to paint Henry Percy as a villain in this final act of Anne’s life, but the truth is much different. With the King of England breathing down their necks, the jury didn’t have any chance to enact justice, and many might have actually believed in Anne’s innocence. Indeed, Percy’s reaction to the verdict was utterly heartbreaking.

65. Her Old Fiance Died Of A Broken Heart

In reality, the decision to execute Anne absolutely destroyed Henry Percy. When an aide read out the decree, Anne’s ex-fiance was so overcome with emotion, he collapsed on the floor, and was so out of it that attendants needed to haul him out of the room. He never got over the shock, either. He passed, childless, a mere eight months later.

66. Henry Falsely Accused Her

Henry may have claimed Anne was treasonous,  but the truth behind Boleyn’s trial is tragic. According to most experts, Henry really did just have her killed because she didn’t give him male children as quickly as he wanted. Besides, now he had his new toy, Jane Seymour, to play with. But Henry did give Anne one last, small, and very disturbing “gift” at the end.

67. She Was Supposed To Be Burned Alive

In accordance with her so-called “crimes,” Anne was supposed to be burned at the stake. However, King Henry was “merciful” enough to commute this fate to a much pleasanter beheading. Then, going above and beyond (please keep reading sarcasm here), he called in an expert swordsman to perform the deed instead of using the average axeman.

Despite these, er, niceties, Anne’s mind began to contort in tragic ways as she awaited her execution.

68. She Went Unhinged

In her final days in the Tower, visitors to the Queen of England described her as eerily calm and even happy. Perhaps this is why she uttered some utterly chilling last words. She reportedly was chatting with a guard about her professional executioner and, in an attempt to reassure the sentry, said, “I hear he’s quite good. And I have a very small neck!” Yet in the dark of the night, Anne’s inner demons came out.

69. She Wrote A Final, Tragic Poem

We may know what Anne Boleyn was really thinking in her final, desperate days. She likely wrote the poem “O Death Rock Me Asleep,” composing it during her very last hours on Earth. In it, Boleyn seems to grapple with her impending death, writing how the execution will release her from her sorrows: “O death! rock me asleep,” the poem says, “Bring me on quiet rest.”

Only, Anne did not go gently to her end. She had one final, desperate act left in her.

70. She Wrote One Last Letter

After four days in the Tower, Boleyn bundled up a package and gave it to her guard to deliver to the king. It was a letter; her very last to Henry. In it, she plead for mercy, writing that “never prince had wife more loyal in all duty, and in all true affection, than you have ever found in Anne Boleyn.” She also made one final heartbreaking request.

71. She Had Last Wishes

In her final letter to King Henry, Boleyn begged him to think of their daughter Elizabeth, and then she humbly asked that Henry would still spare the lives of her brother and the other men accused of being her lovers. It’s a wrenching revelation: At her core, until the very end, Boleyn may have been truly selfless. But it didn’t go her way.

72. Henry Turned His Back On Her

Tragically, Boleyn’s plea fell on deaf ears. Henry was beyond all reason at this point, already imagining all the boy children he would have with Jane Seymour (in a cruel twist of fate, she did give him one). On May 17, Henry sent George and the rest of the men to the chopping block. Meanwhile, Boleyn waited for her own grisly appointment.

73. She Dressed To Impress

On May 19th, 1536, Anne Boleyn walked to her own execution. She was a clotheshorse until the bitter end and made sure to face the gallows in style. For the occasion, the prisoner queen wore a dark grey damask gown with ermine, a red petticoat, and an English gable hood. Like many of Anne’s garments, these carried a secret message.

74. She Sent Out Coded Messages

Anne wasn’t going to go meekly, and her dress sense proved it. As mentioned above, Anne often favored the French style of hood, but on the day of her execution, you’ll note she wore an English gable hood instead. This was an obvious sign that she was an English queen. More than that, only royalty could wear ermine. Yep, Anne made sure to say farewell as every inch the monarch she was. She wasn’t done yet, either.

75. She Made An Unforgettable Exit

When Boleyn went to the block, she begged to address the crowd. Her last words were poignant. She said, “Good Christian people, I am come hither to die, for according to the law, and by the law, I am judged to die…thus I take my leave of the world and of you all, and I heartily desire you all to pray for me. O Lord have mercy on me, to God I commend my soul.”

As she awaited the executioner’s blade, kneeling on the block, she repeated the phrase, “To Jesus Christ I commend my soul; Lord Jesu receive my soul.” Nonetheless, these final words are missing a crucial thing.

76. She Held Out Impossible Hope

Although Anne spoke at length to the crowd, she never once put King Henry in a bad light, nor did she admit any guilt. She had yet another cunning but selfless reason for this: Anne likely didn’t want any of her family to suffer more if Henry tried to punish her long after she was gone. And as Anne’s last seconds came, she maintained this composure.

77. She Died In The “French” Way

Anne Boleyn even died in her own style. While her ladies wept around her, she got them to tie a blindfold around her eyes and then knelt in front of the block. This was a classically “French” style of execution, and itnodded to Boleyn’s signature Gallic-tinged ways. Anne had prepared every last detail, and now it was time to face her end.

As it turned out, King Henry’s swordsman was worth his pay rate: It took only a single stroke to behead the Queen of England. But that didn’t quite mean she was gone.

78. She Haunted Henry

Henry tried his best to forget Anne, fully establishing Jane Seymour in the palace just 11 days after the execution. But it wasn’t that simple. In fact, Henry had such a difficult time erasing Boleyn’s memory, he soon had all likenesses of her destroyed,  and there are no contemporary paintings of her in existence. Still, there were some things Henry couldn’t bear to let go of.

79. Henry Couldn’t Erase Her Memory

According to some historians, there is one sign that Henry was filled with regret about Anne’s fate. Though he destroyed all likenesses of her and even broke down most of the jewelry he had gifted her, he eventually re-purchased several of Boleyn’s possessions and kept more than a few keepsakes with their initials, “H” and “A.”

80. Some Thought She Was Ugly

Not everyone agreed that Anne Boleyn was a hottie. Though many people praised her beauty, others were, uh, less complimentary. Italian diarist Marino Sanuto glimpsed Boleyn once and found himself thoroughly unimpressed. She was “not one of the handsomest women in the world,” he said, sniping at her short height and “swarthy complexion.” But one insult has grown in infamy.

81. She Was An “Eleven-Fingered” Woman

According to a notorious story, Anne Boleyn had an extra finger on one hand. The tales of a bewitching, eleven-fingered queen are alluring, but they’re also sinister. This depiction came from Catholic Propagandist Nicholas Sanders, who had every reason to discredit Boleyn. He also claimed she had a snaggle tooth and an unsightly cyst on her throat.

84. She Died Heartbreakingly Young

To this day, historians aren’t certain when Boleyn was born (likely somewhere between 1501 and 1507), so we don’t even know how old she was at her tragic end. One thing is certain: She was still in the prime of her life when the executioner’s sword hit. With our best guess, the Queen of England was only as old as 35 and perhaps as young as 28 when she died.

82. Her Daughter Honored Her

Although she kept it on the down-low for political reasons, the future Queen Elizabeth loved her mother Anne very much. Elizabeth was only two years old when Anne went to the block and as an adult, Elizabeth quietly honored Boleyn and her family by taking care of their positions at court. She also always kept her mother’s portrait in a locket on her necklace.

83. Her Life Had A Cruel Twist

This is perhaps the most heartbreaking fact of all when it comes to Anne Boleyn. Throughout her three-year marriage to King Henry, she had as many as four pregnancies and three miscarriages. In a cruel twist of fate, all of those miscarriages were sons. More than that, Anne miscarried her last child on the very day of Catherine of Aragon’s funeral. Poetic justice, or ghostly revenge?

84. She Had Secret Admirers

In 2021, historians made a discovery about Anne Boleyn. Scholar Kate McCaffrey found secret messages inside Boleyn’s prayer book, one that she may have held during her execution. Alongside Boleyn’s extant inscription in the book, “Remember me when you do pray / That hope doth lead from day to day,” there were also family names of the people who had held onto the traitor queen’s tome throughout the years, even though they faced grave danger in keeping it safe.

85. She Is An Enigma

Boleyn is truly one of the most fascinating and enigmatic women in history, and our understanding of her legacy has changed in the centuries since her end. Over the years, she has gone from an enchanting witch to a powerless victim to an empowered woman in her own right. Now we know her as one of the most ambitious and intelligent monarchs of her time. 

Sources1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26

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