He was born around 1511, the only son of Sir Richard Weston, the former under-treasurer of the Exchequer. His mother had been one of Katharine of Aragon's ladies in waiting, but both seem to have retired from court before Weston's birth.
Weston started his career at court as a page, and begins appearing in the accounts as someone who gambled with the king and played sporting games, such as bowls and tennis. King Henry seems to have taken a liking to him, and Weston was appointed a gentleman of the privy chamber. As such, he slept in the king's bedroom and helped care for his royal person, bathing him, grooming him and dressing him with the other gentlemen. It was a position of great privilege, and his parents must have been delighted to see him risen so high in the royal favor.
Weston was knighted at Anne Boleyn's coronation. He married Anne Pickering, who was an orphaned heiress that had been made a ward of his father. They had a son, Henry, in 1535.
Weston made his fatal mistake when he began a flirtation with Madge Shelton, Anne Boleyn's cousin. Madge had recently had an affair with the king, and her fiancé, Henry Norris, seems to have been hesitant to tie the knot afterward. Madge was troubled about it, and so Anne talked to Norris, and then decided to speak to Weston about his unseemly pursuit of Madge.
Perhaps the flirtation with Madge had gone too far. Anne's court was a lively place of music, poetry, and the coy dance of "courtly love," but Anne had a firm moral code she expected her servants to follow. Being the mistress of the king was one thing, but it would besmirch the family's honor if Madge became Weston's mistress.
Anne didn't march up to Weston and begin to lecture him; that wasn't her style. She chatted with him with her customary charm, teasingly accusing him of being in love with Madge Shelton and not loving his wife. Weston replied that there was someone in her household he loved more than his wife, or even Madge - Anne.
Anne likely rolled her eyes and said something teasing in return. This was the everyday language of the court. Every man was expected to pay homage to the queen and pretend to be dying of love for her. Katharine of Aragon herself was the recipient of poems praising her beauty and begging for a glance.
But Cromwell was determined to take these conversations literally, stripped of their context and twisted into admissions of guilt. Anne said later that she "more feared" Weston's testimony because he was the one who had stated bluntly that he loved her, rather than hinting and being coy about the subject.
The dates of the alleged offenses were apparently chosen at random. Cromwell didn't even bother to match them up to the court's known whereabouts at the time they supposedly occurred. Why should he expend the effort? No one was actually interested in proof. The queen and the men accused with her were doomed as soon as they were arrested. The swordsman to execute the queen was summoned long before her trial.
Though the verdict of "guilty" was a foregone conclusion, the execution of everyone involved was not. A powerful effort was put behind obtaining a pardon for Weston. John Husee wrote to Lord Lisle:
If any escape, it will be young Weston, for whome importunate suit is made.
The Weston family sought an audience with the king or Cromwell, and they made an offer of 100,000 marks (the modern equivalent of eight million pounds) for his deliverance. Aside from the efforts of the Weston family, Ambassador Eustace Chapuys reports a parade of officials attempting to procure a pardon for him:
notwithstanding the intercession of the bishop of Tarbes, the French ambassador resident, and the sieur de Tinteville, who arrived the day before yesterday, in behalf of one named Vaston (Weston).
In his Tower cell, Weston wrote out a document enumerating his debts, totaling some £925. His is the only written letter or document from any of the people arrested in Anne's downfall. While it's possible that other documents simply have not survived, it seems that some of the other prisoners - Anne and George especially - were not allowed writing materials.
Weston enumerated his expenses to embroiderers, tailors, gambling debts, a fletcher, a barber ... and "a poor woman that Hannesley of the tennis play had married for balls I cannot tell how much," were among them. He begged his family to pay them for him, and ended with this:
Father and mother and wife, I shall humbly desire you, for the salvation of my soul, to discharge me of this bill, and for to forgive me of all the offences that I have done to you, and in especial to my wife, which I desire for the love of God to forgive me, and to pray for me: for I believe prayer will do me good. God's blessing have my children and mine.
By me, a great offender to God.
The condemned were executed in order of rank, which made Weston the third man in line to lay his head down on the block, soaked with the blood of his friends.
He made the expected execution speech, lamenting his "abominations" or sins, and warning the crowd to learn by his example. He died after one blow by the axe. In the view of the Tudors, it was a good, "charitable" death.
One scholar speculated that Weston was confessing to homosexuality with his remark about "abomination," but there is absolutely no evidence to support the assertion. Not so much as a whisper in the court gossip of the day, nor afterward. Cavendish, who disliked the Boleyn faction, accused many of the men of being libertines, but their supposed sins were all with women. Had there been any contemporary rumors to the effect, he would have repeated them.
Thomas Wyatt likely didn't directly witness the execution of the five men from his cell in the Bell Tower, though he probably did see Anne's. The bloody days of May, 1536 broke his heart, as so many of his friends died so Henry could have an easy path to marry Jane Seymour. Wyatt was careful never to accuse the king or directly state the victims were innocent, but he did write a poem to eulogize them.
Ah! Weston, Weston, that pleasant was and young,
In active things who might with thee compare?
All words accept that thou diddest speak with tongue,
So well esteemed with each where thou diddest fare.
And we that now in court doth lead our life
Most part in mind doth thee lament and moan;
But that thy faults we daily hear so rife,
All we should weep that thou are dead and gone.
Weston's body was taken to a grave behind the chapel of St. Peter ad Vincula, buried with that of Mark Smeaton, while Henry Norris and William Brereton were buried in another. George Boleyn, as a nobleman, was buried in the chapel near his sister. No mention is made in the records of shrouds or cerecloth being provided for them. They were probably buried directly in the earth after their clothing was stripped off as a payment for the executioner.
The place where they were buried is now covered by the Jewel House. When it was built, they collected all of the bones they disinterred during the construction and placed them in the chapel crypt. Weston's remains, if they survived, are now buried there.
Weston's widow, Anne Pickering, remarried quickly after his death and lived on until 1582. Weston's son, Henry, was "restored in blood" thirteen years after his father's execution, meaning he got back his titles and could inherit the property of his grandfather. He was made a Knight of the bath at Elizabeth's coronation, and was said to be in her favor.
Elizabeth showed favor to the families of those who had been her mother's friends and supporters, especially those who had died for her sake.