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This thesis attempts to recover the representations of Matilda, Lady of the English, who nearly became queen of England in 1141. In 1127 Matilda became the heir to her father, Henry I, following the death of her brother in 1120. She was unable to claim the throne immediately following her father’s death in 1135, which allowed her cousin Stephen of Blois to do so. With the help of her half-brother Robert, Earl of Gloucester, she launched an unsuccessful war effort to claim her throne in 1139. Modern historians have flatly labeled her a failure due to the fact she was unable to become queen. I analyze the societal context in which Matilda lived as well as contemporary texts to better understand how histories describing the Anarchy have changed over the course of recorded history. The writing of history changed from the brief, episodic, unanalytical nature of medieval chronicles to the more inclusive and researched early modern histories. Additionally, the querelle des femmes in the early modern era concerned the nature of women and their ability to think for themselves and rule. I demonstrate what early modern subjects thought about their own queens by showing how authors and historians wrote about Matilda before, during, and after the reigns of Queens of Mary I and Elizabeth I. In conclusion, I provide evidence that women engaging in the contemporary political arena face many of the same problems that Matilda did nearly a millennium ago.