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August 7, 1574 – Douglas Sheffield Gives Birth to a Son

“Probably” Robert Dudley by an unknown artist

Douglas Howard was the most famous woman you likely never heard of. As the daughter of William Howard, Baron Effingham, the fifteen-year-old Douglas was given a place in the royal household when Elizabeth came to the throne in 1559. A year later, Douglas married John Sheffield, Baron Sheffield; she returned to court after he died in 1568. That’s when things get interesting.

Specifically, she began an affair with Robert Dudley, Earl of Leicester. Elizabeth’s favorite. We know this because, well, little Robert Dudley was born on this day in 1574! There is also a rumor that Douglas and her sister Frances were BOTH sleeping with Robert Dudley, but that remains conjecture (fun fact: Frances went on to marry the Earl of Hertford, in his second of three clandestine marriages).

There is a lot more I could say about Douglas (for example, how she married again, went to France, and became besties with Catherine de Medici) but that will have to be for another post – this one is about little Robert, who remained in England with his dad. Say what you will about Leicester, he was proud of his son. Gave him an excellent education, enrolled him at Christ Church, Oxford in 1587 with the status of filius comitis (Earl’s son), brought him to the Netherlands and then to Tilbury to face the Armada. When Leicester died, he left the bulk of his estate to little Robert, his only child (yes, Leicester and Lettice had a son, another Robert Dudley, but that one died quite young). For the rest of Elizabeth’s reign, Robert proved himself as a seaman/adventurer, even an explorer.

After Elizabeth died, he decided to try to prove his legitimacy – so that he could also inherit the earldom of Leicester (illegitimate, or “natural” children could not own or inherit titles). Douglas agreed to join his suit and claim she had indeed married Leicester (with both Elizabeth and her second husband dead, there was nothing really stopping her). Unfortunately, like Katherine Grey before her, all her witnesses had died and she could not remember the minister’s name…Too, we have a letter that has come down to us, in which Leicester reiterates to Douglas that marriage to her would result in his “utter overthrow,…as I have both at the first and sundry times since plainly declared to you.” As a result, little Robert lost his case.

Douglas died peacefully not too long after that, and Robert left England and settled in Tuscany for a rollicking life. I’m going to gloss over it as it’s past our era. Let’s just say that he somehow got Emperor Ferdinand II to recognize his claim to his grandfather’s Dukedom of Northumberland – recognition which James and England did not appreciate or recognize…though after James died, Charles I created Dudley’s second wife (Alice) Duchess of Dudley for life and, while not restoring his titles and estates, did recognize Dudley’s legitimacy.

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