It's unknown when Bridget was born. Some accounts say 1477, but that's almost certainly incorrect, because she was still having children as late as 1534. She was the daughter of Sir John Wiltshire, who had an estate that bordered the lands of the Boleyn family. Like Margaret Wyatt, Bridget may have known Anne from the time she was young, but there is no record of it.
Like many women of the era, the records of Bridget's life are scant. She first married Sir Richard Wingfield, who was Lord Deputy of Calais and an ambassador to France.
Sir Richard had an interesting life before he married Bridget. He had been the eleventh of twelve sons, raised at Kimbolton Castle. Being so low in the birth order and among so many sons, Sir Richard had to make his own fortune. He became a courtier during the reign of Henry VII, and married Catherine Woodville, Elizabeth Woodville's sister. She was the widow of Jasper Tudor, and sister-in-law to King Edward IV. A very advantageous match for Sir Richard. After her death, Sir Richard married Bridget. Their marriage was very fruitful, and Bridget had ten or eleven children with him.
Bridget came to court sometime before 1520 and was appointed one of Katharine of Aragon's ladies. She is recorded to have been at the Field of the Cloth of Gold, the famous meeting between Henry VIII and King Francis of France. Sir Richard had helped negotiate the meeting between the two kings.
Sir Richard was sent on a diplomatic mission to Spain in 1525, and fell ill of the "flyx," (flux, or diarrhea). His companions wrote home to the king:
PLEASITH it your Highnes to vnderstond that the xv th. day of this monith our company on Maister Wyngfeld, Chancelor of your Duchie fell syk in to a flyx, and the next day we were convided to a greate feste to the bishop of Avila, whider we went and Maister Wyngfeld with vs, thinking hymself strong ynough thervnto, where he dud ete Millons and drank wyn without water vnto them, and afterwardes dranke bere, whiche is made here by force bytter of the hoppe for to be preservyd the better agaynst the intollerable hetis of this contrye. And albeit he did ete but verey moderatly; yet after our retorne home not oonly his flux began to encreace vpon hym, but also the feuer toke hym farvently. Wherupon Phisicions were callyd for help, who after they perceyved the fever to bee contynuall without intermission and the flux to encrease to a voyding of blud, mynestred vnto hym suche medicynes as they thought moost convenyent; and after the Emperor, hering of his disease, sent all his Phisicions vnto hym to vysyte hym, but for no thing that all they cold doo, the fever could be remedyed, nor yet mean found to make hym slepe, or sleke his perpetuall and ardent thurst; wher vpon he made hym mete to God, and receyvyd all the sacramentis of holy churche, and the xx th day of this monyth whiche was Mary Magdalens day dipartyd owte of this transitory lyf...
A lytell before his dethe he wrote a Letter vnto your Highnes to pray the same to bee good and graciouse to my Lady his wif [Bridget] and his childer, whiche your Grace shall receyue herwith. We have buried hym as honorably as we could devyse of things to be had here, bicause he was bothe of your Ordre and your Ambassador. His will was to bee buryed at the ffreres Obseruaunts, bilded in this Citie by the late King of Aragon and quene Elizabeth pro sepultura Regum, wher no man is buryed without lycence of the Emperor, for the opteynyng wherof after we sent to know his pleasure, he not oonly gladly gaue lycence but also comaundyd he shuld be buryed within the cyrcuit of the quere, which place is foundyd and reseruyd for bury all oonly of Kings. Whiche thinge he dyd in the honor of your Highnes, and never bifore was grauntyd to no pryvate person.
Sometime around this period, Bridget left court, and it seems she'd had some sort of quarrel or problem, though as to what it was, the records are silent. Anne Boleyn wrote a letter to Bridget, the only one of her letters to a woman friend which survives. It was written after 1525 when Anne's father held the title Viscount Rochford, but before his elevation to Earl of Wiltshire in 1529.
I pray you as you love me, to give credence to my servant this bearer, touching your removing and any thing else that he shall tell you on my behalf; for I will desire you to do nothing but that shall be for your wealth. And, madam, though at all time I have not showed the love that I bear you as much as it was in deed, yet now I trust that you shall well prove that I loved you a great deal more than I fair for. And assuredly, next mine own mother I know no woman alive that I love better, and at length, with God's grace, you shall prove that it is unfeigned. And I trust you do know me for such a one that I will write nothing to comfort you in your trouble but I will abide by it as long as I live. And therefore I pray you leave your indiscreet trouble, both for displeasing of God and also for displeasing of me, that doth love you so entirely. And trusting in God that you will thus do, I make an end. With the ill hand of
Your own assured friend during my life,
There's a current theory that Bridget was blackmailing Anne, but there's no evidence. We only know that Bridget's "indiscrete trouble" was upsetting to Anne, and she saw it as sinful, but she wanted Bridget to know she still cared for her.
Bridget remarried in 1529 to Sir Nicholas Harvey (or Hervey). Harvey was in favor with the king, and is mentioned in the chronicles of the day as a "diligent and faithful" servant. It probably helped that he was an athletic jouster, a sport highly favored by the king. Harvey is recorded as riding in the lists at the Field of the Cloth of Gold.
He must have been well-educated, because it's known that he spoke Flemish and French, which helped secure him an appointment as ambassador to Ghent. He was also known to be a "strong partisan" of Anne Boleyn and worked in foreign courts to advance the king's case for his annulment from Katharine of Aragon.
Harvey was out of the country quite a bit, but he and Bridget managed to have five children together, raising her total to a whopping fifteen or sixteen kids. He was recalled to England in 1532 to serve in Parliament, possibly to voice his support of the impending marriage, but Harvey didn't serve in that capacity for long. He died in August, 1532 at Ampthill, where Katharine of Aragon was being lodged at the time, leading some to speculate he had been sent to try to convince her to accept the inevitability of the king's marriage to Anne Boleyn.
In October 1532, Anne Boleyn and Henry VIII stopped to visit Bridget's home on their way to Calais. It would have been only a couple of months after the death of Bridget's husband. They stayed again on the return trip in November.
However, there seems to have been another unpleasant situation, and historians can only speculate as to what it was.
Bridget married for a third time to Sir Robert Tyrwhitt. Some theorize that Anne chastised Bridget for remarrying so fast after the death of her husband, or because Bridget had been acting inappropriately with Tyrwhitt even before Harvey's death.
Perhaps Anne simply disliked Bridget's choice of a husband, because Tyrwhitt was known to be hostile to Anne. Tyrwhitt supported Princess Mary, and was close friends with the Duke of Suffolk, husband of Mary Tudor Brandon, who despised Anne.
Shortly after she married Tyrwhitt, Bridget died, possibly in childbirth. 1533 was the last year she received a New Years gift, so it must have been sometime in 1534 that she passed away.
Two years later, during Anne Boleyn's trial, testimony was given that Bridget had given a confession about Anne Boleyn on her deathbed. One of the jurors, John Spelman, noted:
"Note that this matter was disclosed by a woman called the Lady Wingfield who was a servant of the said queen and shared the same tendencies. And suddenly the said Wingfield became ill and a little time before her death she showed the matter to one of her etc."
What that testimony was, we do not know, because the records of Anne's trial have vanished. Anne's letter to Bridget ended up in Cromwell's papers, possibly used as evidence to support the deathbed assertion.
There has been much debate over what Bridget could have confessed ... Possibly what she saw of Anne and Henry's sexual intimacy during their stay in her home on the visit to Calais. On the return trip, Anne and Henry were likely married, so they may have shared a bed beneath Bridget's roof. If she was not aware of the secret marriage, Bridget may have thought Anne was fornicating.
Or the testimony could have concerned Anne's relationship with Thomas Wyatt before she married the king. Thomas Wyatt seems to have believed that the Duke of Suffolk was responsible for his arrest, and may have thought the allegation came from Tyrwhitt's wife.
Bridget's testimony could only have been about Anne's life before she married the king. Bridget left court before Anne's marriage to Henry, so she could not have testified about the claims of incest and adultery Anne was facing in her trial.
But, in my opinion, the question should be whether Bridget made a "confession" about Anne at all. Why would a dying woman be primarily concerned with confessing the sins of another person, especially if they were activities which were already widely known, such as Anne and Henry's cohabitation on the Calais trip or Anne's relationship with Wyatt? If the information was important enough to trouble the mind of a dying woman, why did it continue to remain secret for another two years, until after Anne had already fallen?
Some have guessed it was because everyone was afraid to speak against Anne, but Katheryn Howard's sins only stayed secret for little more than a year after she married the king, and he was known to be more passionately in love with her than he had been with his other wives.
As I previously noted, Tyrwhitt was hostile to Anne, and the hope of her partisans was that if Anne was gone, Henry would restore Mary to favor. It could be entirely possible that Tyrwhitt exaggerated something his wife had once told him, or that he'd heard from gossip, in order to gain favor with the king who clearly wanted his wife out of the picture. Secondly, if Bridget did die of complications from childbirth, it's entirely possible she would have been delirious in the final hours of her life, and could have said anything.
None of the other witnesses to the trial report any explosive revelation coming from Bridget's testimony. Indeed, Spelman himself sums up all of the allegations: "all the evidence was of bawdery and lechery..." but apparently, not worth specifying. It's of particular interest to note that Spelman said Bridget "shared the same tendencies" as the queen. What tendencies was Tyrwhitt accusing his wife of having? A taste for adultery and incest? That seems unlikely. A tendency for flirtation? More plausible.
In the end, it seems Bridget's testimony was not a smoking gun, but another brick in the wall.