When you think of Henry VIII executions, his wives immediately come to mind. Out of his six spouses, he had two beheaded. But the tragic fates of those women are just part of the story when it comes to people who were close to the King before they wound up dead. The King was determined to get his way, was fearful of traitors, and often maintained order by eliminating anyone he perceived to be a threat; not even Henry VIII's advisors were safe. The establishment of the Anglican Church brought out countless rebels who fought against royal supremacy, and as Henry VIII struggled to produce an heir, rivals were constantly on the horizon.
No one was safe if the scent of treason was in the air. Traitors were put on trial, though they were typically executed. The ways Henry VIII had people killed were meant to send a message; they were usually hanged, drawn, and quartered, though many of the King's associates were given a gracious death by beheading. Former confidants including Thomas More, Thomas Wolsey, and Thomas Cromwell were all put to death at the King's command.
Thomas Wolsey died of natural causes, but he most likely would have been executed had he lived long enough. Wolsey held numerous church and governmental positions under Henry VIII, actively reformed both, and took part in international diplomacy as well. He was Lord Chancellor from 1515-1529, and held an immense amount of power, wealth, and influence.
Henry needed Wolsey to use his connection to Rome to secure an annulment of his marriage to Catherine of Aragon so he could marry Anne Boleyn. Wolsey was unable to do so, and was dismissed as Lord Chancellor in 1529. He was later arrested on charges of treason and taken into custody in northern England, but died on his way to London on November 29, 1530.
Thomas Cromwell did a lot for Henry VIII, the Anglican Church, and the royal administration. And, in some ways, all of this got him killed.
Cromwell was of low social status, but made his way up through the ranks in the service of Thomas Wolsey. After Wolsey's fall, Cromwell became a member of Parliament, where he used his intelligence and international experience to get the attention of the King. Henry made Cromwell Privy Counselor in 1531, and he became a close advisor, confidant, and like-minded reformer for the King.
From 1532 on, Cromwell was the principle force behind the English Reformation. He became vice-regent for spiritual matters in 1534, which allowed him to dictate policy and finance to the entire clergy. He was also charged with reforming monasteries, but by 1540, all of the monastic institutions in England were closed and their property was in the hands of the King. None of this made Cromwell any friends, and there was a Parliamentary pushback against his policies beginning in 1539. For his part, the King, threatened by Cromwell, was determined to keep him in his place as well.
Cromwell's biggest error happened when his advised Henry to marry his fourth wife, Anne of Cleves, shortly after the death of Jane Seymour late 1539. Henry hated Anne and never forgave him for getting him into the marriage. Despite a brief upswing in his relationship with Henry in early 1540, by June Cromwell was accused of treason and heresy. He was condemned to die without a trial, and beheaded on July 28.
Sir Thomas More, born in 1478, was an Oxford-trained lawyer who once considered becoming a monk. His political career as secretary and advisor to Henry VIII led to him becoming a close confidant of the King. More served as a foreign diplomat and was knighted in 1521, all the while earning a reputation as a scholar as well. More was a devout Catholic and actively wrote against heresy and in defense of orthodoxy. In 1529, More became Lord Chancellor as Henry continued his efforts to divorce Catherine of Aragon.
As an avid defender of Catholicism, More persecuted heretics as Lord Chancellor. He refused to sign a request to the Pope for Henry's divorce in the early 1530s and disagreed with the King over heresy laws, and when Henry declared himself to be head of his newly-created Church of England, More resigned his chancellorship. More also refused to take the oath acknowledging Henry as the head of the English Church in 1534. He was arrested, put on trial for treason, and condemned to death in 1535. More was beheaded on July 6, 1535 at Tower Hill.
Edward Stafford, 3rd Duke of Buckingham, and his family found favor during the reign of Henry VII (r. 1485-1509). Under Henry VIII, Stafford held the positions of Lord High Constable and Lord High Steward, served in the English army, was appointed to the King's Privy Council, and participated in diplomatic audiences and royal events. Stafford was wealthy and well-connected, and due to his family lineage, Henry became suspicious of him in 1520. Henry commissioned an investigation into allegations that Stafford claimed he sought to overthrow the King.
The King himself interrogated witnesses in 1521, and Stafford was put on trial for treason in May of the same year. He was accused of listening to "prophecies of the King's death and of his own succession to the crown, and of having expressed an intention to kill the King." The 17 peers who heard the case found Stafford guilty of treason, and he was sentenced to death. He was beheaded at Tower Hill on May 17, 1521. In 1523, he was posthumously dispossessed of all lands and titles.