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  • Writer's pictureHannah Fawcett 🦭

The Battle of the Boleyns – Anne vs Mary; which sister was the more scandalous of the two?

(Natalie Portman and Scarlett Johansson in The Other Boleyn Girl)


When you think of the Boleyn sisters, which one do you think of first? Anne or Mary? Most people would think of Anne first as she is known in history as being the second wife of Henry VIII of England. However, there was also Mary who caught the King’s eye first, and as many argue, she was the one who imprinted scandal on the Boleyn Family and Anne subsequently learned not to make the same mistake. In a way, it could be argued that Anne pursued marriage to Henry to bring back her family’s good name to what it was before Mary’s affair with Henry, and she hoped people would forget about Mary and her behaviour. However, the fates of the two sisters are different but they both end in disgrace. So, Mary died in poverty while Anne was executed for treason. They are both fates we associate with downfall, and it is clear to see that both sisters faced a sad end to their lives. I believe Anne is the most remembered though due to becoming Henry’s wife, but she is remembered for committing adultery.


This article will explore which Boleyn sister was more scandalous. 


To begin with, historians argue which Boleyn sister was born first. One side believes that Anne was the oldest being born around 1507 and because Anne obtained a position in the household of Margaret, Archduchess of Austria. The opportunity would usually go to the eldest daughter first. Therefore, most historians believe Mary was born a year later in 1508. However, Mary was married off first which is unusual for the time as typically the eldest daughter would receive the honour first. However, Mary supposedly already had a scandalous reputation before her marriage. It was argued that Mary was known at the royal court first as supposedly being a previous mistress of Francis I of France when she was at the French royal court and Francis reportedly named her the ‘English Mare.’ Therefore, this may have led Mary’s father, Thomas Boleyn to arrange her marriage to limit the amount of scandal caused. 


On 4th February 1520, Mary was married to Henry VIII’s attendant, William Carey. The king is rumoured to have attended the wedding and this is where the affair started to occur. As it was during her marriage to Carey, it is difficult to establish if the two children Mary gave birth to were fathered by Henry. Mary’s first child was a daughter, born in 1524, and who was named Katherine. Mary gave birth again, to a son in 1526. He was named Henry, and he is the child that is widely believed to have been fathered by the king. In portraits, he has a physical resemblance to the king, and he was given the title of Lord Hunsdon by his cousin, Elizabeth I. Mary’s marriage during her affair to William, acted as a safety net as if her children were fathered by Henry, it did not matter as she was a married woman so people would assume they were her husband’s children but rumours did persist about her son’s true parentage. I believe the affair was known as Henry had admitted his affair with Mary when being questioned if he had an affair with Anne’s mother as well, but he stated, ‘Never with the mother.’ 


In history, Mary is remembered as Henry’s mistress most of all. For example, English History states ‘Mary Boleyn was the sister of King Henry VIII’s second wife, the infamous Anne Boleyn. But she was also the king’s mistress before her sister’s ascendancy.’ (1) Here is it clear to see how Mary is remembered. Also, the affair took place during the time of her family’s rise to power and not everyone at the royal court was allied with the Boleyns as they were from humble roots, so the court would have looked down on Mary. It would have been seen that Mary was having an affair with the King to further her family’s interests. A way not unusual in the royal court as royal mistresses were provided for. However, the act of having an affair was scandalous during this time but Mary was in some way protected by her marriage to Carey. Despite both men and women participating in an affair, most of the time, the woman was blamed for starting it and subsequently, shamed. Alison Weir’s biography of Mary is titled: Mary Boleyn: ‘The Great and Infamous Whore.’ This nickname is a reminder of Mary’s position as a previous royal mistress. I find this unfair as we do not know if Mary wanted to have an affair with Henry or whether she was forced to by her family. 


Mary was widowed in 1528 and was left in a difficult financial situation. Therefore, this suggests that her affair with the king had ended by then as normally royal mistresses were well established during their position. Also, it was the time when Anne was noticed by Henry, so Mary was pushed out of the spotlight and essentially forgotten. This was mostly likely caused by her previous scandalous behaviour despite probably being manipulated by her family to pursue the king’s interests and sleep with him. However, she did attend the visit to France with the king and Anne to meet Francis I and she may have attended Anne’s coronation is 1533. Most likely, Henry would have wanted to forget about Mary as he was now married to her sister and so, he wouldn’t want people to remember their affair. Indeed, Henry’s marriage to Anne was seen as unlawful due to his previous relationship with Mary, and this explains why Henry would not acknowledge any children by Mary.


Despite, her father and brother being elevated in society, Mary received little rewards and married for a second time for love to William Stafford in 1534. This was the cause of her fall from favour including from her family. Mary was banished from court for marrying Stafford a low-born in secret and becoming pregnant by him. As History Hit describes, ‘Mary’s crime was to fall in love with a soldier, William Stafford, and become pregnant by him.’ (2) This is interesting as it symbolises that Mary’s marriage to a low-born was worse than having an affair and was more scandalous. A point that suggests that Mary was seen as more scandalous is that Mary never regained favour. It is not known whether she had any communication with Anne before her execution. It is difficult to trace her life after this time. 


However, Mary’s previous relationship with Henry may have helped him to divorce Anne which led to her execution, so Mary’s previous scandalous behaviour caused more scandal for her family. Her brother was executed along with Anne. It is most likely that Mary died in poverty around July 1543. Her legacy lived on through her two known surviving children. Her daughter Katherine became a maid of honour to Henry’s fourth wife, Anne of Cleves, in 1539. Her son, Henry, served in the royal household. Queen Elizabeth I showed great favour to her cousins. It may have been because of their rumoured parentage, especially Mary’s son, Henry. Also, English History states ‘Henry granted the Careys actual manors and estates during the affair and immediately before the child’s birth.’ (3) This is in some way an acknowledgement that Henry was the son of the king and thus, they receive some royal favours from him. Furthermore, I find it interesting that Mary’s children gained royal favour despite her scandalous behaviour. Whereas Elizabeth I was always seen as a daughter of a ‘whore’, and she lived in the shadow of her mother’s legacy. 


Philippa Gregory’s book, The Other Boleyn Girl, is based loosely on Mary Boleyn’s life. The title suggests that Mary is in some way forgotten in history which suggests that Anne was more scandalous than Mary, but she will be remembered as Henry’s mistress. A role which Anne refused to become and tore England away from Rome to protect her reputation through marriage to Henry. She tried to not fall in disgrace like her sister but ultimately failed. In the film adaption of the book, Mary’s son, Henry, was born during the affair with the king and is regarded as Henry’s child. During the scene when Mary gives birth, we see that Henry is acknowledging the child due to be born as his, but Anne arrives and captures his attention. It is evident in this scene that Henry wants Anne and not Mary. Anne promises hope that one day she will be his wife right after her sister has given birth to a son. Therefore, Henry moves on from Mary and does not end up acknowledging his son which leaves Mary in disgrace and Anne high up in royal favour. Instead of supporting her sister, it is portrayed during this scene that she snatched Henry’s heart and made him forget about her sister. This relates back to the belief that Anne was determined to be different than her sister. 


Compared to Mary’s life, Anne’s life is well-documented as she became the second wife of Henry VIII. This is a significant difference to Mary as Anne refused to sleep with Henry until she became his wife. Anne spent her early years in one of the most prestigious courts of the time. She began to serve in the household of Margaret of Austria and then was sent to the French royal court. This would be the place where she learned all the skills needed to be a woman in the Tudor times. She learned how to sing, play musical instruments, and dance. She also adopted new French royal fashions which she brought to England when she returned. All About History’s Anne Boleyn and the Six Wives explains how Anne made some form of scandal at the French royal court as being flirtatious and was well-known. (4)


Anne had returned to the English royal court in 1522 and the relationship between Anne and Henry deepened after 1527. Henry had offered her the position of official royal mistress, but Anne refused. Anne did not want to end up in the same position as her sister and she supposedly despised Mary for choosing to be a mistress. On the topic of which Boleyn sister was the most scandalous, it is evident that Anne did not want to be the one known as the most scandalous at the royal court. During the King’s Great Matter, which was when Henry tried to get a divorce from his current wife, Catherine of Aragon, Anne was hated and many at the royal court were on Catherine’s side. Anne was seen as a ‘whore’ and some suspected her of being a witch due to her behaviour to have Henry as her husband. So, despite not sleeping with Henry, Anne was regarded as a ‘whore’ anyway, a word attached to scandal. Also, Anne was attempting to take away another woman’s husband. This is something that would be scandalous during our own time as it is seen as a common thing not to have an affair with a married man. 


However, Anne had eventually slept with Henry before their secret marriage in 1533 and had become pregnant which meant the divorce proceedings needed to be hastened along. It is not known whether this was consensual or whether Anne was raped, which has been suggested by some historians. Anne had gone against her own wishes and slept with Henry before marrying him, the same as her sister did but Anne did eventually marry him. However, their marriage was in secret so this can affect the legitimacy of the marriage. It was like when Elizabeth Woodville and Edward IV married in secret. This case led to their son, Edward, being labelled as illegitimate and barred from the English throne as it was argued that his parents were not lawfully married. Of course, Elizabeth I would be regarded as illegitimate throughout her life and this label would stick with her throughout her reign. Anne had tainted her daughter with scandal. 


When the marriage between Catherine and Henry was annulled, Anne was crowned Queen of England in Westminster Abbey. However, her marriage with Henry would be affected by the birth of a daughter, Elizabeth, on 7th September 1533. She had gone against the main aim of her and Henry’s marriage, to produce a son. Henry was furious as he had broken England away from Rome just to marry Anne. Anne would not give birth to a son which weakened her position at court and made Henry’s eye wander. He began to take an interest in Jane Seymour, one of Anne’s ladies-in-waiting. In the TV series, The Tudors, Anne caught Henry and Jane together while pregnant and this eventually led to her miscarrying a son. Indeed, Anne had a stillborn and a miscarriage. The miscarriage had occurred five days after the King had fallen from his horse and consequently, Anne had blamed her miscarriage because of the shock of the accident. For a wife to blame a husband for something in Tudor times was scandalous and unthinkable. 


Anne’s failure to produce a male heir sealed her fate. She would be removed as Henry’s wife. Thomas Cromwell drew up charges of adultery against her which made Anne guilty of treason, the worst crime you could commit, and which carried a death sentence. To many, Anne was guilty and the fact that she had committed adultery against the King was shocking and she was once again labelled as a ‘whore’ and a witch. No one considered her innocence; this is most likely because of all the decisions she had took. She was even accused of committing adultery with her own brother which was also incest and was seen as the most shocking crime of all. On 2nd May, Anne was sent to the tower, and she never saw her daughter again. On 18th May, her marriage to Henry was declared invalid on the basis that Anne had been pre-contracted to another man and Anne was executed the next day. To many, she had abused her position as Queen and used Henry for her own gains. She had also failed in her number one duty, to produce a son. None of her family acknowledged her and it is believed that Mary did not come to her execution due to their strained relationship. Anne had protested her innocence to the very end. 


Both sisters have been portrayed in TV series and movies. They are usually both mentioned with Mary as Henry’s mistress and Anne as his eventual wife. In Anne of The Thousand Days, Henry is quickly bored with Mary and becomes infatuated with Anne. It is evident that Anne is portrayed as more able to capture and maintain Henry’s attention. Anne had been precontracted to marry the son of the Earl of Northumberland but because Henry had taken a liking to her, he made sure the contract was broken. So, here Henry is making sure Anne won’t be married during a potential affair with him. In this movie, Anne refuses to acknowledge Henry and give in to him. To refuse a King something he desired was essentially treason, but Anne had the courage to say no. This is something that needs to be credited for. Therefore, how can Anne be considered the most scandalous as she did not give up herself whereas Mary did, but it is important to consider that Mary may have been forced to. Anne’s refused to be an obedient wife continues to be portrayed in this movie as she refuses to sleep with Henry unless he removes Thomas More from office. In this take on history, Henry gives Anne a choice before condemning her to death. He says that if she agrees to annul their marriage and make Elizabeth illegitimate then she can live but Anne refuses as she does not want to betray her daughter. Could this have happened in real life? 


In The Tudors, Mary is presented as a sexually driven woman. She submits to be Henry’s mistress and just steps aside when she is no longer needed. Anne is shown as a woman constantly rejecting Henry’s advances and keeps him on edge. When she is married, she hates Henry having mistresses despite it being a normal thing in that era. Wives are excepted to not interfere with their husband’s mistresses and to turn a blind eye to them. Anne may have learnt not to do this at the French royal court. There is also an element of Anne’s family forcing her to pursue Henry for their own gains. She also works to remove Woley’s influence on Henry on behalf of her family who hated Wolsey. Indeed, Anne and Wolsey did not get along. Going back to the pressure both sisters would have been under from their family, Mary is pressured by her family to become Henry’s mistress in The Other Boleyn Girl whereas Anne captures Henry’s attention on her own.


To conclude, while Mary seemed to have submitted to scandal and did not do much to regain her good name, Anne was also hated for her flirtatious behaviour which led to her execution as she was accused of committing adultery. However, Anne tried so hard to make sure she did not end up like her sister and she saw her sister as morally wrong. When she became Queen, Anne could have helped Mary when she became poor as she was in a similar situation to Anne once. The only difference was that Mary did not attempt to marry Henry. Anne defied the status quo; she gained influence on Henry during the early years of their relationship, but this declined after she gave birth to Elizabeth. She refused to be an obedient Tudor-style wife which was scandalous. However, since Mary had an affair with Henry, she is ultimately seen as the most scandalous, but Anne’s actions and fate will be remembered in history as also scandalous. It is important to remember that they were both essentially commoners, but their father had a noble title, and he came from humble beginnings, and it was done with Mary’s and Anne’s help and influence on the King.  



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