Elizabeth Tailboys was born around the year 1520. She was the daughter of Bessie Blount, mother of Henry Fitzroy, who was the only illegitimate child Henry VIII ever recognized. Elizabeth was acknowledged by Bessie’s husband, Gilbert Taiboys, 1st Baron Tailboys of Kyme, but it is suspected that she was the daughter of Henry VIII. Henry treated his illegitimate daughter well and arranged her marriage to Thomas Wymbish, a very wealthy man. Thomas had become a ward of the crown following the execution of his guardian. Thomas was engaged to his guardian’s daughter, but Henry broke that off so he could marry Elizabeth, in 1539.

Elizabeth was very unhappy with Thomas. Once her father and two older brothers had died, their barony was left to her, so she became the 4th Baroness Tailboys of Kyme. Her husband, who was rich but not noble, wanted a title, so he petitioned to have himself named “Lord Tailboys”. Elizabeth was strongly against this since she was not so fond of Thomas. Henry VIII intervened on his daughter’s behalf, and it was ruled that Thomas could not obtain his wife’s titles if the marriage was childless, which it was. Thomas was always bitter about this, and when he died, he left close to nothing to his wife in his will.

In 1553, Elizabeth married again to Ambrose Dudley, 3rd Earl of Warwick. If the name “Dudley” rings any bells, then it’s probably important to note that Ambrose was the brother of Guildford Dudley, the husband of Lady Jane Grey, who famously reigned for nine days. He was also the brother of Robert Dudley, the great favorite of Queen Elizabeth I. Elizabeth died ten years later, in 1563, aged around forty-three, and as she was childless, her barony became extinct.