Medieval and Tudor mistresses occupied a fascinating and controversial role in history, shaping the politics, culture, and court life of their time. Far from being mere companions, these women wielded considerable influence, using their proximity to monarchs to advocate for allies, secure wealth, and navigate the treacherous waters of royal intrigue.
Figures like Alice Perrers, Jane Shore, and Katherine Swynford exemplify the complex lives of mistresses, blending ambition with survival in an era of rigid societal expectations. From the shadowy corridors of medieval courts to the glittering courts of Tudor England, the stories of these women reveal a hidden history where charm, intelligence, and resilience often determined their fates. This exploration delves into the lives of royal mistresses, uncovering their enduring impact on history and their remarkable ability to navigate power, scandal, and the ever-present threat of downfall.
Rough transcript of Episode 266: Medieval and Tudor Mistresses
We are going to talk about a very unique type of woman in history, and that would be the mistresses. So a lot of people have a lot of opinions about mistresses, especially royal mistresses, noble mistresses, but it’s true that they were very much a part of court life.
They were much, very much a part of life, as indeed they likely still are. And they have a very complicated and controversial place in history, and we’re going to talk about them. We’re going to talk about some famous mistresses throughout medieval and Tudor England and what the role of the mistress was.
Royal mistresses, far from being just footnotes to kings lives, they could wield considerable influence in politics, court intrigue, and culture. These women were not officially recognized, yet their relationships with powerful men gave them access to wealth and a voice in decisions that shaped kingdoms.
So this episode will explore the lives of royal mistresses in medieval and Tudor England. Figures like Alice Perrers and Jane Shore, who managed to survive the treacherous world of court politics, and later women like Anne Basset and Mary Boleyn, show a hidden world of ambition, survival, and scandal.
Alice Perrers: The Lady of the Sun
Let’s start out with Alice Perrers. Alice, later known as Alice of Salisbury or Alice of Windsor, was born around 1348. Her exact birthplace and family background are unclear, but some evidence suggests that she may have belonged to the Hertfordshire’ Perrers family. Other accounts, likely biased by contemporary disdain, claim that she was the daughter of a thatcher “from the town of Henney”.
Around the age of 12, she married a Janyn Perrers, a London jeweller who died within a few years, leaving her a widow by her mid teens. Her entrance into the royal court came through service to Queen Philippa as a damsel or attendant.
By 1366, at the age of 18, she had caught the attention of Edward III who was then 55. Their affair began while Queen Philippa was still alive, and Alice bore the king at least three children during this time. Despite her lack of noble lineage or striking beauty, chroniclers noted Alice’s wit, charm, and a melodious voice that compensated for her physical appearance.
Edward’s affection for her grew stronger after the Queen’s death in 1369, and he rewarded her lavishly. She amassed immense wealth, including 56 manors, castles, and townhouses. Alice’s influence became increasingly controversial as Edward aged and his health declined. Accused of exploiting his senility, she reportedly convinced him to buy her the same jewels repeatedly, reselling them for cash.
Edward even paraded her through London in golden robes as the “Lady of the Sun”, inciting public criticism. Between 1370 and 1376, she used her position to manipulate court proceedings, ensuring favorable outcomes for herself and her allies. Her dominance made her deeply unpopular among nobles and the public.
In 1376, during the Good Parliament, Alice was accused of corruption, and they made the King banish her. An ordinance specifically prohibited her from participating in any legal cases, a practice that she had apparently abused to protect her vast estate. Her properties, including over 21, 000 pearls, were confiscated. Despite this, she managed to return and regain some of her lands after Edward died in 1377.
Now in 1375, she had married Sir William of Windsor to secure her position after Edward’s death, though the union produced no children. She spent her remaining years attempting to recover her full estate. She died in the winter of 1400 to 1401 and was buried at the Church of St. Lawrence in Upminster in Essex.
Her story is marked by ambition, scandal, and resilience, and it lives on as a cautionary tale of the risks and rewards that women could face when they became a king’s mistress in the medieval court.
Jane Shore: The Merry Mistress
Now we’re going to talk about Jane Shore, the merry mistress of Edward IV. Jane Shore was born Elizabeth Lambert around 1445 in London. She was the daughter of John Lambert, a prosperous merchant, and Amy Marshall. Raised in relative comfort, she received an education unusual for women of her class. Her intelligence, charm, and quick wit gained her attention at a young age, earning her admirers among the city’s elite.
Thomas More later wrote that her personality, more than her physical beauty, captivated those around her. She was described as merry in company and skilled in conversation, with an innate ability to put people at ease. She married William Shore, a goldsmith and banker, in her early 20s. But the marriage was annulled in 1476 on the grounds of his impotence.
Shortly after, Jane caught the eye of King Edward IV, who was known for his many romantic entanglements. Their affair began in 1476 and lasted until Edward’s death in 1483. Unlike other royal mistresses, Jane was not showered with extravagant gifts. Instead, she used her influence to plead for mercy on behalf of those who had fallen out of favor, earning her a reputation for generosity and compassion.
Her advocacy reportedly saved Eaton College from disillusion, a legacy they still remember in the Jane Shore Society. Following Edward’s death, Jane became embroiled in the power struggles of the time. She formed relationships with Thomas Gray, Edward’s stepson, and William Hastings, Edward’s loyal supporter.
Accused of conspiring against Richard III, Jane was arrested and publicly humiliated, forced to perform penance by walking through London in a thin shift with a candle in her hand. After her penance, Jane was imprisoned in Ludgate, where she caught the attention of Thomas Lynom, Richard’s solicitor general.
Despite Richard’s objections, they married, and Jane lived out her remaining years in relative obscurity, her fortunes diminished. She actually survived all the way until about 1527, her early brilliance dimmed by a life marked by both privilege and hardship.
Katherine Swynford: The Scandalous Duchess
Now we’re going to talk about a royal mistress love story that actually ended well, which is Katherine Swynford, the scandalous duchess who changed England’s royal lineage.
Born Katherine de Roet around 1349, likely in Hainault, Katherine grew up in a family connected to the English court. Her father, Payne de Roet, was a herald knight who accompanied Queen Philippa of Hainault to England. So that’s under Edward III when we’ve got Alice Perrers being born and then eventually becoming the mistress, having served in the same Queen Philippa’s household, right?
So a lot of mistresses happening. Katherine and her siblings, including her sister Philippa, who married Geoffrey Chaucer, were raised at court under the Queen’s patronage. This upbringing afforded Katherine an education, social polish, and connections that would shape her future. Katherine married Sir Hugh Swinford, a knight in the service to John of Gaunt, Duke of Lancaster, around 1361.
They lived modestly at Kettlethorpe, a manor in Lincolnshire, and had several children. Then, Hugh died in 1371, and Katherine’s position became precarious. To support herself and her children, she joined the household of John of Gaunt’s second wife, Constance of Castile, as a governess to the Duke’s daughters.
This role brought her into close proximity with Gaunt, sparking a love affair that scandalized the realm. Between 1373 and 1381, Katherine and Gaunt had four children, the Beauforts, named after one of Gaunt’s estates in France. Despite their illegitimacy, these children were legitimized by the Pope in 1396 after Katherine and John of Gaunt married following the death of his second wife.
Their union was, of course, highly controversial, viewed as a shocking departure from noble norms. Chroniclers like Thomas Walsingham denounced Katherine as a social climber, but her lasting relationship with Gaunt suggests mutual affection and loyalty. Katherine’s children with John of Gaunt profoundly influenced English history.
Her great grandson, Henry VII, founded the Tudor dynasty, claiming the throne through his mother, Margaret Beaufort. Katherine’s descendants include every English and British monarch from the Tudors onward. After Gaunt’s death in 1399, Katherine retired to Lincoln, where she lived quietly until her death in 1403. She was buried at Lincoln Cathedral. Her tomb is a site of reverence for her prominent descendants.
Katherine Swynford’s legacy endures as the matriarch of a lineage that shaped England’s destiny and the enduring power of love amidst scandal.
Anne Stafford: The Tudor Temptress
Now we’re going to talk about some of the early Tudor mistresses, starting with Anne Stafford. Lady Hastings was born around 1483 into the very powerful Stafford family. Her father, the Duke of Buckingham, and her mother was Katherine Woodville, the sister of Elizabeth Woodville, Edward IV’s queen, so she was Edward IV’s niece. With her Plantagenet lineage, Anne was a prominent figure at court, carrying the prestige and peril of noble blood in an era where politics often turned deadly.
Her brother, Edward Stafford, Duke of Buckingham, would later lose his life in 1521. accused of treasonously entertaining prophecies about Henry VIII’s failure to produce a male heir. Anne’s connection to scandal stems from a rumored affair with Henry VIII, a claim that has tantalized historians but remains unproven.
This event, however, caused enough uproar to disrupt courtly life. The events unfolded in 1510 while Katherine of Aragon was pregnant with her first child. Anne, along with her sister Elizabeth Stafford, served as one of Katherine’s ladies in waiting. Elizabeth grew suspicious of Anne’s interactions with the king and alerted their brother, the Duke of Buckingham.
Enraged at what he perceived as the king’s inappropriate attention toward his sister, Buckingham confronted Sir William Compton, a close confidant of Henry and allegedly an intermediary for the affair. The scandal erupted into full blown confrontation. Buckingham, unwilling to accuse the king directly, withdrew from court, and Anne’s husband, Lord George Hastings, sent her to a nunnery 60 miles away to cool the controversy.
Henry retaliated by banishing Elizabeth Stafford from court, incurring Katherine of Aragon‘s wrath. According to the Spanish ambassador Chapuys, Katherine wept and ranted at her husband, angered by his infidelity and the exile of her favorite lady in waiting. Yet Anne’s marriage to Lord Hastings seems to have weathered the storm, producing seven children and letters that speak of affection and mutual respect.
Anne Stafford remains a figure shrouded in ambiguity. Was she truly Henry’s mistress or simply a pawn in the power games of Tudor politics? Either way, her story captures the volatile mix of ambition, loyalty, and scandal that defined life at Henry’s court.
Bessie Blunt: Mother of Henry Fitzroy
Next, Bessie Blunt. She holds a unique place in Tudor history as the mother of Henry VIII’s only acknowledged illegitimate child, Henry Fitzroy. Born around 1498 to Sir John Blunt and Catherine Peshall of Kinlit in Shropshire, Bessie came from a respectable but unremarkable gentry family. Her father’s loyalty to the crown included service in Henry VII’s campaigns in France, but the family rose to greater prominence through Bessie’s relationship with the king.
Little is known about Bessie’s early years, but she is remembered for her beauty, vivacity, and her grace. She joined the court as a maid of honor to Katherine of Aragon, where her dancing, singing, and charm captured the attention of Henry. By 1514 or 1515, she became his mistress. a position she held for several years, longer than most of Henry’s extramarital affairs.
At court, Bessie became the king’s favored companion, excelling in courtly entertainments. In 1519, she bore the king a son, Henry Fitzroy, later created the Duke of Richmond in Somerset. Fitzroy was the only illegitimate child Henry VIII ever officially acknowledged. His birth was a testament to the king’s ability to have healthy male heirs.
A significant point during a time when Katherine of Aragon’s pregnancies resulted in repeated losses, the saying “Bless ‘ee, Bessie Blount” became a popular refrain celebrating her contribution to the Tudor legacy. Despite the significance of Fitz Roy’s birth, though Henry’s affair with Bessie ended shortly afterwards, possibly due to his growing interest in Mary Boleyn.
Unlike other royal mistresses in European courts, Bessie was never formally recognized in an official capacity. Her role remained discreet, though her impact on the dynasty was substantial. In 1522, she married Gilbert Talboys, a baron, with whom she had three children.
Their marriage took her to Lincolnshire, where she lived quietly, removed from the intrigue of court. However, letters from Fitzroy’s tutor suggest that Bessie maintained some involvement in her son’s upbringing, alongside Henry’s notable affection for his son. After her husband died in 1530, Bessie remarried Edward Clinton. This union produced three daughters.
Briefly, Bessie served as a lady in waiting to Anne of Cleves, but ill health cut her time at court short. She died in 1540, likely from tuberculosis. Though overshadowed by Henry’s queens and other mistresses, her legacy did endure through her son Henry Fitzroy. In the 1520s, Fitzroy’s legitimacy as Henry’s heir was briefly contemplated during the king’s quest to annul his marriage to Katherine.
His existence underscored Henry’s belief that his marriage was cursed, fueling the great matter and England’s break from the Catholic Church. Though, of course, none of that mattered because Fitzroy himself passed away in 1536.
Mary Boleyn: The Other Boleyn Girl
Then there’s Mary Boleyn, often overshadowed by her ambitious sister Anne. She gained notoriety as the mistress of two kings potentially, Francis I of France and Henry VIII of England, and later became a figure of quiet resilience after her fall from royal favor.
Born around 1499, her life offers a lens into the precarious positions that women of the Tudor age often found themselves in. She was born at Blickling Hall, just like Anne, and then raised at Hever in Kent. She was the oldest of three surviving Boleyn children, and she received a well rounded education typical of her station.
Around 1514, she joined the household of Princess Mary Tudor, who was traveling to France to marry Louis XII. It was during this time that Mary’s reputation became tarnished by rumors of promiscuity, allegedly becoming the mistress of Louis successor, Francis I. Francis himself later referred to Mary as a great whore, though such claims may have been exaggerated to discredit the Blinns.
Mary returned to England in 1519 and soon married Sir William Carey, a prominent courtier. Despite her marriage, she became a mistress to Henry VIII. The affair’s timeline and duration are unclear, but it likely occurred in the early 1520s.
Unlike Bessie Blunt, Henry’s previous mistress, Mary’s relationship with the king resulted in no acknowledged offspring, although it has been widely speculated that her two eldest children, Catherine Carey and Henry Carey, were fathered by Henry VIII.
However, Henry never formally claimed them. While Mary’s affair with Henry faded, her younger sister Anne rose to prominence. Anne refused to become Henry’s mistress, likely seeing what happened to her sister. And, of course, then it led to the great matter and Henry annulling his marriage to Katherine of Aragon, setting the stage for Anne’s ascent to power.
Mary’s life was less glamorous, though. Her husband, William Carey, died in 1528, leaving her in a great amount of debt. Anne was now a key figure at court. and arranged for her nephew, Mary’s son, Henry Carey, to be placed in a prestigious monastery and secured Mary a modest pension. Despite these efforts, though, the sisters were not close, and Mary’s role at court diminished as Anne’s influence grew. I would imagine it would likely be quite awkward for these two sisters, who were both with the same man.
Now, in 1534, Mary secretly married William Stafford, a soldier of modest means. This marriage was seen as a social misstep and it angered both Queen Anne and King Henry. Mary and Stafford were banished from court and the Boleyn family disowned her.
Financially struggling, Mary appealed to Thomas Cromwell and even wrote a heartfelt letter defending her marriage, stating she chose love over ambition. Although Anne sent a conciliatory gift, Mary was not reinstated at court. Mary lived quietly with her husband in Essex, fading from the historical record.
She didn’t visit Anne or George, their brother, during their imprisonment in the Tower of London, nor is there evidence of her presence at Anne’s execution in 1536. Mary died in 1543. Likely at Rochford Hall, and her burial place is unknown. Mary had four known children, Catherine and Henry Carey, from her first marriage, and possibly two children, Edward and Anne Stafford, from her second.
Her children, particularly Katherine and Henry Carey, rose to prominence during the reign of their cousin Elizabeth. Henry Carey was ennobled as Baron Hunsdon, and became a trusted figure in Elizabeth’s court. Catherine served as one of Elizabeth’s ladies-in-waiting. Then we’re going to talk about the later Tudor period.
Anne Basset
For example, Anne Basset, the stepdaughter of Arthur Plantagenet, who was Henry VIII’s uncle, was widely rumored to have been one of Henry VIII’s later mistresses. A maid of honor to both Jane Seymour and Katherine Howard, Anne was described as beautiful and ambitious, fitting the profile of women who caught Henry’s attention.
Despite the persistent rumors though, no concrete evidence confirms Anne’s relationship with the king. Historians speculate that the stories might have originated from court gossip or political maneuvering as Anne’s family had much to gain from such a connection.
Elizabeth Vernon
Then there was Elizabeth Vernon, the mistress and later wife of the Earl of Southampton. Her story is a reflection of the shifting attitudes towards mistresses in Elizabethan England. As a maid of honor to Elizabeth I, Elizabeth Vernon became involved with Henry Wriothesley, the Earl of Southampton.
Their passionate relationship caused scandal when Elizabeth became pregnant out of wedlock. The couple married in 1598, but their actions enraged the Queen, who briefly imprisoned both of them for their indiscretion.
Unlike earlier mistresses, though, Elizabeth Vernon’s story did not involve a monarch, but a prominent nobleman. Signaling a cultural shift, and also, there was no king on the throne, and it’s not like Elizabeth was going to be having a lot of affairs, so it did change the culture. By the late Tudor period, mistresses were less likely to be tied to the crown, as the cult of Elizabeth’s chastity discouraged such relationships at court.
Lady Penelope Devereaux
Similarly, Lady Penelope Devereaux, the sister of the Earl of Essex, was celebrated for her intelligence and beauty. She was the inspiration for Sir Philip Sidney’s Astrophel and Stella , one of the great works of Elizabethan poetry. While rumors linked her romantically to Sidney and other courtiers, her actual role as a mistress remains unclear.
What sets Penelope apart is the way she leveraged her connections to influence politics. She became deeply involved in her brother’s rebellion against Elizabeth I, using her charm and social standing to rally support. Penelope’s life demonstrates how women could navigate the courtly world of romance, intrigue, and power without necessarily being tied to a royal figure.
The Role and Legacy of Mistresses
Then let’s talk about the role of mistresses. Power, survival, and scandal, mistresses often wielded influence in ways that official advisors or even queens could not. Their proximity to the king gave them access to his private thoughts and decisions, allowing them to advocate for allies, secure patronage, and shape court politics.
Alice Perrers, for example, successfully lobbied for lucrative land grants and positions for her supporters, while Jane Shore used her charm to mediate disputes and assist those seeking royal favor. This influence, though, came with risks. A mistress’s favor was tied directly to the king’s affection, making her position precarious.
Once their relationship ended, mistresses were often vilified, stripped of their wealth, or cast out of court entirely, as we saw with Alice Perrers and Jane Shore. Society viewed mistresses with a mix of fascination and disdain.
In medieval England, royal mistresses like Katherine Swynford were sometimes forgiven if their relationships led to legitimate unions. By contrast, Tudor era mistresses often faced harsher scrutiny, reflecting the era’s growing emphasis on morality and public decorum. Scandals involving mistresses could spark political crises. Anne Stafford’s brief affair with Henry VIII created tensions between the king and her powerful family.
Similarly, Elizabeth the Vernon’s premarital pregnancy and secret marriage to the Earl of Southampton enraged Queen Elizabeth I, who valued her court’s reputation for chastity. The public also enjoyed a good gossip about these relationships, of course. Ballads and plays often sensationalized the lives of royal mistresses, turning women like Jane Shore into tragic figures or cautionary tales.
These stories reflected societal anxieties about power, sexuality, and female ambition. For every mistress who thrived, many more were discarded when their influence waned. The very qualities that brought them favor beauty, charm, and wit often became liabilities when court politics shifted. Mary Boleyn, for instance, was eclipsed by her sister Anne, and her relationship with Henry ultimately brought her little lasting benefit.
Even those who achieved prominence lived under constant threat. They could be used as scapegoats in political conflicts, blamed for the king’s unpopular decisions, or targeted by rival factions. The legacy of Medieval and Tudor mistresses is complex. In their own time, they were derided as symbols of moral corruption.
But their stories show a more nuanced reality. Many of these women were survivors, using the limited tools available to them charm, intelligence, and connections. To carve out spaces of power in a male dominated world. In literature and art, royal mistresses have been reimagined as everything from seductresses to tragic heroines.
Jane Shore became a fixture of English ballads, while Katherine Swynford’s romance with John of Gaunt inspired novels and historical fantasies. So the lives of medieval and Tudor mistresses show a hidden layer of history where women without official titles shaped court politics. influenced royal decisions and became pivotal figures in the stories of their times.
Their stories reflect the challenges of navigating a world that offered women few official avenues to power. They were not just companions to kings, but survivors of a courtly system that could both elevate and destroy them. Each one faced unique struggles, whether managing public scrutiny, avoiding political entanglements, or securing a future after their fall from favor.
Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast,  the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.
She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).
