This post comes from the highlights of Janet Wertman’s talk on Douglas Sheffield at Tudorcon 2024
The Unheard Story of Douglas Sheffield: Love, Legacy, and Power in the Tudor Court
At Tudorcon 2024, attendees were treated to a fascinating deep dive into the life of one of the lesser-known but no less compelling women of the Tudor era—Douglas Sheffield. While her name might not evoke the immediate recognition of an Anne Boleyn or Catherine of Aragon, her life offers a quintessential example of the strength and complexities of women navigating the Tudor court. Douglas’s story intersects with some of the most powerful figures of the time, including Robert Dudley, Queen Elizabeth I, and Catherine de Medici. But it’s more than just her relationships with men that make her story noteworthy—her life represents resilience, intelligence, and the ability to make choices in an era where options for women were often few.
A Noble Heritage and Promising Start
Born into the prominent Howard family, Douglas Sheffield was well-positioned from birth to play a role in the Tudor court. Her father, William Howard, was a younger son of the infamous Duke of Norfolk, one of the most powerful men of his era. Though her family’s fortunes waxed and waned with the shifting political alliances of the Tudor reigns, Douglas found herself well-placed when she joined Queen Elizabeth I’s court as a young woman.
Her family’s political influence, particularly through her brother Charles Howard, Lord High Admiral, allowed Douglas access to opportunities that few other women had. It was during these early years at court that she would first cross paths with Robert Dudley, Queen Elizabeth’s favorite and one of the most powerful men in the kingdom.
The Affair with Robert Dudley
It’s impossible to tell Douglas’s story without addressing her relationship with Robert Dudley. The two began a passionate affair in the early 1570s, and in 1574, Douglas gave birth to Dudley’s son. This relationship is one of the key reasons why Douglas’s name has been remembered in history—though, as the session at Tudorcon pointed out, this fact alone doesn’t do justice to her personal strength and character.
Dudley, famously linked to Queen Elizabeth herself, had long been a source of intrigue at court. And while his relationship with Elizabeth remained a tantalizing “what-if” for historians, Douglas’s relationship with him was very real. Despite the birth of their son, however, Dudley refused to marry her, citing political and social reasons that would make such a union impossible. His rejection didn’t end Douglas’s story; it only made her more determined to control her own fate.
A Woman of Independence: Douglas’s Life Beyond Dudley
One of the standout moments in the Tudorcon talk was the emphasis on how Douglas took control of her destiny after Dudley. Refusing to be a pawn in the political games of the Tudor court, Douglas did not allow Queen Elizabeth to pressure her into a marriage she didn’t want. When Elizabeth suggested Douglas could marry Dudley after he had already fathered her child, Douglas declined. This moment demonstrated her remarkable fortitude in standing up to the queen herself—something few women of the time dared to do.
Not long after, Douglas married Sir Edward Stafford, a prominent courtier and diplomat. Their marriage marked a new chapter for Douglas, as she accompanied him to France, where they became close to the powerful French queen Catherine de Medici. The connection Douglas made in the French court only furthered her prominence, showing that her story was not simply about the men in her life but about the way she deftly navigated the upper echelons of both English and French political spheres.
A Fight for Legitimacy: Douglas’s Son and the Court Battle
One of the most dramatic episodes in Douglas’s life came later, when her son—born of her relationship with Robert Dudley—sought to prove his legitimacy and claim the title of Earl of Leicester. Douglas stood by him, even testifying that she and Dudley had secretly been married. The trial became a public scandal, drawing intense attention from the highest levels of society. Though the court ultimately rejected her claims, Douglas’s tenacity during the proceedings reflected her lifelong commitment to protecting her son’s rights and her place in history.
Why We Should Remember Douglas Sheffield
As we reflect on the session at Tudorcon, it’s clear that Douglas Sheffield’s life is much more than a footnote in the story of Robert Dudley. Hers is a story of resilience, strength, and the ability to carve out a path in a world dominated by powerful men. Yes, she is remembered for her relationship with Dudley, but her life was filled with significant moments of influence, particularly in her later years at the French court.
In the end, Douglas was a woman of her time who used the tools available to her—marriage, court alliances, and her intelligence—to maintain her influence and protect her family’s legacy. Her story reminds us that the women of the Tudor court were more than just wives, mistresses, or daughters—they were individuals with their own agency, navigating the dangerous waters of Tudor politics with grace and determination.
Douglas Sheffield’s life was filled with triumphs and challenges, yet she maintained her dignity, resilience, and independence throughout. Her story offers a lens through which we can understand the broader complexities of women’s roles in the Tudor period, and why figures like her deserve to be remembered. Far from being just a love interest in Robert Dudley’s life, Douglas Sheffield was a formidable figure in her own right, making choices that defined her legacy long after the Tudor era.
To explore these fascinating stories and more, you can gain full access to the Tudorcon 2024 video collection. Learn directly from expert historians about the intricacies of Tudor life, politics, and power—right from the comfort of your home.
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).
