Henry VIII’s hitmen: the Tudor king’s secret hunt for traitors

Bribery, subterfuge, kidnap and murder by paid assassins. As Robert Hutchinson reveals, when it came to neutralising enemies of the English state – even those living abroad – Henry VIII would stop at absolutely nothing

Seeking to remove opponents who questioned his right to be head of church and state, Henry VIII was ruthless in his pursuit of those he deemed traitors. (Image by Alamy)

Cardinal David Beaton made a lot of enemies during his short career as lord chancellor of Scotland. Serving from 1543–46, the fiercely Catholic Beaton first enraged Scotland’s Protestants by arresting a friar called John Rogers for preaching heretical doctrine, and throwing Rogers into a dungeon at St Andrews Castle, his seat of power. Beaton then incurred the wrath of the influential reformist, John Knox, by having George Wishart, a Protestant preacher and Knox’s mentor, burned at the stake.

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But of all the foes that Beaton made in the 1540s, none was more powerful than King Henry VIII. Beaton had been one of the most vigorous opponents of Henry’s attempts to impose greater English influence on Scotland, and he had helped the papal ambassador Mark Grimani evade a kidnap attempt by the king’s agents while sailing to Scotland. But, in the spring of 1546 Beaton’s defiance of the English monarch would have bloody consequences. At daybreak on 29 May, 17 assassins, secretly funded by Henry, broke into St Andrews Castle hellbent on teaching Beaton a lesson. First they murdered the castle’s porter, hurling his bloodied body into a ditch. Then they fell on the cardinal himself, dragging him from his bedchamber and hacking him to death. Soon after, Cardinal Beaton’s mutilated corpse could be seen dangling from a window by sheets tied to an arm and a foot. This was a humiliating fate for one of Scotland’s most powerful men. Henry insisted that his involvement be kept secret because he maintained, with sublime hypocrisy, that “such business is not meet for kings”.

Beaton wasn’t the first nor the last victim of Henry’s relentless pursuit of those he deemed to be traitors and enemies – a pursuit that stemmed both from religious turmoil and the Tudors’ tenuous, if not legally fragile, right to the throne. In the 1530s, Henry extended treason laws to penalise those uttering disloyal words, or opposing the king’s religious supremacy, his choice of wives, or the status of his wives and any royal offspring. Hundreds would die as a result.

Cardinal Beaton’s mutilated corpse was dangled from a window, a brutal and humiliating fate

Throughout the rest of his reign, Henry showed scant respect for tiresome diplomatic protocol or kingly comportment when it came to neutralising threats to his crown or ambitions. It’s this that explains his little-known enthusiasm for conspiracy and clandestine operations.

Henry was probably involved in an audacious plot to kidnap his nephew, James V of Scotland (1512–42), on Scottish soil and carry him off to London. Meanwhile, the brutal death of Cardinal Beaton confirmed the English king’s capability to orchestrate assassinations north of the border. But Henry’s shadowy war with men he deemed enemies of the state wasn’t confined to Scotland. He arguably went to even greater lengths to eliminate his foes on mainland Europe.

The royal hitlist

The king’s chief target was Cardinal Reginald Pole (see boxout below), a theologian who actively sought England’s return to papal authority following the break with Rome. As the king’s bête noire, an “arch traitor”, as Henry called him, Pole escaped numerous attempts by English agents to kidnap or kill him. But Pole was far from alone. In total, around 130 clergy or laymen with traditional religious beliefs fled England between 1533 and 1546 as the English Reformation gathered momentum. Henry feared that “such men would have the opportunity to work their treason” overseas, and so he dispatched agents to hunt them down.

This meant that men such as Robert Brancetour – an associate of Pole, reported “now in Italy, devising the king’s destruction [and persuading] princes to levy war against the king” – had to be constantly watchful. In December 1539, one of Henry’s diplomats, Sir Thomas Wyatt, learnt that Brancetour was in Paris as part of the entourage of Charles V of Spain, who was on a state visit to France. Wyatt asked the French king, Francis I, to sanction Brancetour’s extradition. Brancetour was, in Wyatt’s words, “a man of small quality who had been a merchant’s factor and robbed his master and since… had conspired against [Henry]. There was no one that bore more malice to [the king] than he.” Francis acquiesced, ordering his provost to accompany Wyatt during the arrest.

They went “without light” to Brancetour’s lodgings. While trying to gain entry, Wyatt fell, badly hurting his leg. His sudden entrance, like a pantomime villain, stunned Brancetour. “His colour changed as soon as he heard my voice and the provost set hand upon him,” Wyatt recalled. Wyatt tried to snatch letters from a table but “he flung them backwards into the fire. Yet I overthrew him and caught them out [of the flames]”. Wyatt had ensnared his prey, although not for long. Brancetour insisted he was Charles V’s servant and he demanded that the provost deliver him to the Spanish king. The French official, finding himself in deep diplomatic waters, departed to seek fresh instructions.

Henry’s brother monarchs proved reluctant to repatriate those seen by the king as traitors

Meanwhile, Charles V prevaricated over agreeing to extradite Brancetour, saying he would consider whether any treaties applied in this case after he returned to Spain. “I tell you plain, I will speak for his deliverance both to the constable of France and to the [French] king and I trust they will not do me so great a dishonour as to allow one that serves me to suffer damage,” the Spanish king told Wyatt. “Even if your master had me in the Tower of London, I would not consent to change my honour and my conscience.” The next morning, the French freed Brancetour and he went to Rome to meet Pole.

Banged up abroad

If Henry’s brother monarchs proved reluctant to repatriate those Henry believed to be traitors, the fugitives themselves were just as slippery in escaping the king’s grasp, as the case of Gregory Dudley, son of John Sutton, Lord Dudley showed. Disguised as a labourer, Gregory escaped from England to hide in English-held Calais. He later went to Paris, where another of Henry VIII’s diplomats, Sir William Paget, found him in February 1543.

Paget obtained a blank warrant from the French for Dudley’s extradition and kept “this miserable fool” in custody. Dudley obligingly scribbled a treason confession. “He begged for mercy with more tears than I ever saw distil from any creature’s eyes,” Paget reported. “If there be no greater malice in him than appears, he might be pardoned.” But just nine days later, Dudley got away. Paget begged Henry’s pardon for the escape of “this false traitorous boy Dudley” who, while eating his supper, “whipped out at the door and was out of sight [in the street] before that beastly fool, his keeper, could open the door and follow”.

Two English agents, Edward Raleigh and John Brant, spotted the fugitive in Milan that April. Should they detain him, or just kill him on the spot? Murdering him could be “unprofitable” since they might lose vital intelligence won during interrogation. However, seeking his arrest would be “difficult in a free country where papists bear much rule”. The Milan governor agreed to hold Dudley but he slipped away once more, heading for the safety of papal territory. Fortunately for the duo, they tracked him down again and he was imprisoned. In August, though, Brant brought bad news: “That naughty person Dudley [was] suffered to escape out of Milan castle.”

Grim nonchalance

With traitors proving so infuriatingly elusive, more direct action was required. An unlikely instrument of the king’s vengeance came in the guise of a shadowy Italian mercenary, Colonel da l’Armi. Henry hired da l’Armi ostensibly to recruit mercenary soldiers. In reality his mission was to kill Henry’s hated enemy, Reginald Pole.

Da l’Armi arrived in Venice in January 1545, at the same time that the Venetian magistrates commissioned four paintings for their headquarters near the Rialto Bridge. One was The Massacre of the Innocents, portraying a massacre of infants perpetrated by King Herod’s soldiers. The picture includes a handsome bearded figure nonchalantly watching the carnage. A retainer, alongside, has a shield bearing the da l’Armi arms. So the bearded man must be Henry’s Italian hitman – and this painting could be described as the most expensive wanted poster in the history of criminology.

The Vatican’s intelligence network soon discovered da l’Armi’s presence in Venice and his true mission. Edmund Harvel, Henry’s ambassador in Venice, reported (wrongly, as it happens) that Pole had refused to attend the church’s council at Trento in north-east Italy, for “fear of his life” because “of such captains… [serving] your majesty”. William Paget chillingly described da l’Armi as having a “vengeful wit and naturally disposed to work mysteries. Such a man, at such a time, is to be cherished,” he said. The Catholic authorities doubtless saw matters differently, and hired a posse of 13 assassins to kill da l’Armi before he could get to Pole. The pre-emptive strike failed and da l’Armi remained at large.

Henry’s campaign to eliminate his enemies was audacious, sinister and brutal, yet ultimately it failed

By May 1545, the 77-year-old pope, Paul III, was sufficiently concerned to tell Francesco Venier, Venetian envoy to the Vatican, that da l’Armi was planning a “terrible crime” and was awaiting a gentleman of Henry’s Privy Chamber to deliver instructions – expected within 12 days. The pope added: “We see this villain near at hand. He deserves a thousand deaths… The king of England… a heretic, is plotting mischief… The council is sitting [at Trento]. There is Cardinal Pole, whom these ruffians may have been ordered to kidnap, or take sinister action against him.”

If da l’Armi was attempting to evade his pursuers’ attentions by keeping a low profile, he failed miserably. In August 1545, he was involved in a fight with the Venetian night-watch that resulted in a watchman being seriously wounded – a crime punishable by death. Da l’Armi only avoided this fate when Harvel persuaded the Venetian authorities – keen to protect “valuable investments” held by Venetian merchants in England – to back off. Then it was discovered that da l’Armi had hired thugs to murder a mercenary officer, Count Curio Bua, in Treviso. They stabbed and slashed at him two or three times, which he survived, before riding off.

In November 1546, the Italian merchant banker Mafio Bernardo was stabbed 18 times and murdered. A letter was found in Bernardo’s bloodstained doublet, a letter da l’Armi had given to the killers, men he called his “intimate comrades”. Henry’s assassin had thus far maimed and murdered with impunity. But his luck was about to run out. Da l’Armi quit Venice again and, in January 1547, attended a glittering entertainment in Milan. Despite wearing a mask, he was recognised and detained. The Venetians had their man. But would realpolitik prevent the Venetians from prosecuting da l’Armi? Henry’s death in January 1547 provided the answer. Fears that Henry would scrap his alliance with the city state if it mistreated da l’Armi died with the English king – and so, in May 1547, da l’Armi was escorted to Venice’s Piazzo San Marco and beheaded.

This swaggering cutthroat’s career very much reflected Henry VIII’s campaign to eliminate his enemies in Europe. It was audacious, sinister and brutal, yet ultimately it failed. Cardinal Reginald Pole – the “arch traitor” so loathed by Henry – would live to fight another day.

Robert Hutchinson is a historian. His new book, Henry VIII: The Decline and Fall of a Tyrant, was published by Weidenfeld & Nicolson in April


Book: The Tudor Law of Treason: An Introduction by John Bellamy (Routledge, 2013)

You can read more about Henry VIII at historyextra.com/henryviii

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This article was first published in the May 2019 edition of BBC History Magazine