We don't have an authenticated portrait of him. The portrait by Holbein labeled Ormond is likely to be the cousin with whom Thomas disputed over the title. The only reliable image we have is the likeness in the brass etching on the top of his tomb.
Thomas was born around 1477 to Margaret Butler and Sir William Boleyn, likely at the family estate of Blickling Hall. He was the second son after his brother, James.
Around 1500, Thomas married Lady Elizabeth Howard, eldest daughter of the Duke of Norfolk, a very prestigious match. We're unsure of the exact date. Elizabeth's jointure was settled on her in the summer of 1501, and jointure was usually settled within about a year of the marriage, though there was no exact time limit.
Elizabeth was currently a "bargain" on the marriage market, likely with a modest dowry, because her family was in disgrace. She may have also had a bad reputation.
John Skelton, poet laureate under Henry VIII, wrote a poem dedicated to her in 1495 entitled, To My Lady Elizabeth Howard.
Troilus, I vow, if that he had you seen,In you he would have set his whole delight:
Of all your beauty I suffice not to write,
But, as I said, your flourishing tender ageIs lusty to look on, pleasant, demure and sage.
Skelton's comparison of Elizabeth to Cressida (who betrayed Troilus) could have been subtly mocking Elizabeth's lack of morals. As Alison Weir says,
Maybe Skelton was merely praising Elizabeth's beauty, but if so, he had chosen a strange and compromising comparison, when there were plenty of others to be drawn.
Quite a few writers of the day who were hostile to her daughter claimed that Henry VIII and Elizabeth had an affair, which Henry denied. False rumors are not uncommon in this day, but this one persisted. It's possible that Elizabeth's reputation made her vulnerable to accusations such as these.
Elizabeth did not have a long-term appointment at court - unusual for the wife of a man as favored as Thomas - though whether or not that was her personal choice is unknown. Perhaps she simply wanted to stay home at Hever with her family. She was frequently pregnant in the early years of her marriage. Later in life, Thomas wrote:
When I married I had only 50£ a year to live on for me and my wife as long as my father lived, and yet she brought me every year a child.
Together, they had at least five children, but only three survived to adulthood: Mary, Anne, and George. The graves of two young sons are extant.
Thomas probably had little emotional attachment to his children. He was away from home at court, or at an ambassadorial post for most of their childhoods, and noble child-rearing customs of the day did not encourage closeness. Though the children seem to have had genuine and mutual affection for one another, most family relationships were based on loyalty and duty, not emotion.
Anne Boleyn may have inherited her intelligence, charm, and charisma from her father, who was very successful in his diplomatic career and made many friends in the countries where he was appointed. Desiderius Erasmus described Thomas as "outstandingly learned," and dedicated two of his books to him. Henry VIII would once say that he had no equal as a skilled negotiator.
Thomas had his negative qualities, too. He was described as stingy and avaricious. But on the whole, he was liked by his contemporaries, a necessary quality in his line of work.
As ambassador to the Netherlands, Thomas got to know Margaret of Austria well enough that in 1514, she agreed to accept his daughter, Anne, as a maid of honor despite her very young age.
Mary Boleyn was sent to France that same year, when she was about fifteen years old. She was a maid of honor for Mary Tudor Brandon, but remained in France after the princess was widowed and returned to England. During the five years Mary Boleyn was at the French court, she may have become the mistress of Francis I.
We have no records who show how Thomas Boleyn and his wife, Elizabeth, felt about this. Author M.L Bruce writes that they disliked Mary because it. In any case, the Boleyn family did not benefit in any substantial material way from this short-lived affair, and it's likely that the incident (or at least the rumor it happened) lowered Mary's value in the marriage market.
When Mary returned to England, she became the mistress of Henry VIII. This relationship can be confirmed with a reasonable degree of certainty but it was short-lived. However, after it ended, Henry found Mary a husband, William Carey.
Thomas's career was flourishing. His skills as an ambassador got him appointments as an envoy to Charles V, to the court of Spain, and France. He was one of the ambassadors who helped make arrangements for the Field of the Cloth of Gold, the famous meeting between King Henry VIII and King Francis I, and he was present at the meeting of Henry and Charles V. He was given grants of land and court offices. By 1525, he had an income of about £800, making him a very wealthy man.
When Henry fell in love with Anne Boleyn in late 1525 or early 1526, Thomas probably wasn't best pleased. While the king was interested in his daughter, no other noble would offer for her hand, and Anne's marriage had already been a subject of some difficulty.
Anne continued to resist the king's advances, but Henry wasn't getting tired of her refusals and moving on to a more receptive target. The more time passed, the more nervous Thomas probably got about the situation. Anne was becoming known internationally as "the Great Whore." Who would marry her if the king's scheme to rid himself of Katharine of Aragon failed? The family may have scorned Mary Boleyn for fornicating with the king, but at least she was safely married now. It was forward and upward for the Boleyns, or else, utter ruin.
The king's showered gifts and favor on the Boleyn family. Thomas was made Viscount Rochford, and then Earl of Wiltshire and Ormond. In 1530, after Wolsey's fall, he became Lord Privy Seal.
Henry sent Thomas to meet with Emperor Charles and the Pope to convince them of Henry's annulment suit. At the time, Henry was still maintaining the fiction that he wanted to remain married to Katharine of Aragon, but felt compelled to make sure their marriage was really valid. The theft of Henry's love letters to Anne Boleyn earlier in the year belied his stance that Anne was just a virtuous maiden of the court he happened to be flirting with. Sending Anne's father to negotiate with Katharine's nephew and the pope must have seemed particularly galling to those two.
An interesting incident is related by Foxe in regards to this visit. Supposedly, Thomas refused to do the customary homage of kissing the pope's bared toe. Foxe likely relates this story to show that Thomas shared his daughter's reformist faith, though Thomas was not what would be identified as a Protestant today.
Howbeit, one thing is not here to be omitted, as a prognosticate of our separation from the see of Rome, which then chanced by a spaniel of the earl of Wiltshire. For he, having there a great spaniel which came out of England with him, stood directly between the earl and the bishop of Rome, when the said bishop had advanced forth his foot to be kissed.
Now whether the spaniel perceived the bishop's foot of another nature than it ought to be, and so taking it to be some kind of repast or whether it was the pope's will of God to show some token by a dog unto the bishop of his inordinate pride, that his feet were more meet to be bitten of dogs, than kissed of christian men - the spaniel (I say), when the bishop extended his foot to be kissed, no man regarding the same, straight-way (as though he had been of purpose appointed thereunto) went directly to the pope's feet, and not only kissed the same unmannerly with his mouth, but, as some plainly reported and affirmed, took fast with his mouth the great toe of the pope, so that in haste he pulled in his glorious feet from the spaniel : whereat our men smiling in their sleeves, what they thought, God knoweth.
Henry finally cut the Gordian knot and declared himself head of the church in England. He married Anne Boleyn in November of 1532 and crowned her queen. Thomas must have been elated. He could have never imagined the fortunes of the Boleyns rising so high. He had every reason to believe his future grandson would be the king of England.
But things did not go as planned. Anne Boleyn's child was a girl, and she had miscarriages afterward. And then came the shocking news that the widowed Mary Boleyn had disgraced the family by marrying a minor gentleman of the court.
In late 1535, Henry's attentions began to wander to a girl of the Seymour family, despite the Howards' efforts at luring him back to their side. In May, 1536, Anne was arrested on trumped-up charges of adultery and incest with her brother, George. Both were sent to the Tower.
In one fell swoop, the power of the Boleyn faction was crushed. Anne's supporters were imprisoned with her, or neutralized with fear. In the Tower, Anne asked for her father, and worried her mother would "die of sorrow," when she heard the news.
What did Thomas do? The records of the era show nothing but an echoing silence. Thomas Wyatt's father sent Cromwell letters about his son, which are recorded in the Letters and Papers of Henry's reign. But there is nothing from Thomas Boleyn, nor Elizabeth. Jane Parker was apparently the only one to contact George Boleyn during his incarceration. Beyond that, there is nothing.
There are no surviving letters to Anne or George from their parents, but that is not certain evidence they never existed - we know some records and papers were destroyed in the Cottonian Library fire in the 1730s. However, if any were sent, they probably would have been mentioned by Kingston, as the letter from Jane Parker is.
Thomas was recused from having to sit on the jury that would condemn his children. His only living son died one day before his daughter knelt under the executioner's sword. Neither Thomas nor Elizabeth were recorded as witnessing the execution. We don't know where they were, but it seems likely they had retreated to Hever.
Thomas lost his position as Lord Privy Seal, and two years later, lost his lands in Ireland as the long-battled suit over the Ormond title was decided in the favor of Thomas's cousin.
Thomas still served his king. He is recorded as having assisted with quelling the uprising of the Pilgrimage of Grace, and he was present at the christening of Henry's son with Jane Seymour.
There may have been some sort of breakdown in Thomas and Elizabeth's marriage, because Elizabeth was buried in Lambeth with her Howard ancestors after she died in 1538. Thomas considered remarrying, but he died himself about a year later and was buried in the Hever chapel beside one of the sons that died in infancy.