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Tudors on the brink: how the dynasty almost ended before it even began
Henry Tudor’s stunning victory at Bosworth won him the English crown – but also, writes Sean Cunningham, condemned him to a life dogged by conspiracies, rebellions and suffocating paranoia
Published: November 11, 2026 at 3:30 PM
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The chances are that you’ve never heard of the battle of Blackheath. Yet at this seemingly minor clash, contested just south of the Thames and Greenwich Palace in June 1497, the reign of Henry VII – and the fate of the extraordinary dynasty that would go on to transform England – teetered on the brink.
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The country was in uproar. In May, an uprising had erupted in the south-west, ignited by intolerable levels of taxation levied by Henry to fund his military campaigns. By early June, a rebel army had swept through Devon and Somerset and was heading for London, declaring openly its intention to bring about regime change. One false move in this febrile moment and Henry VII’s still-fragile rule could have been shattered.
The king’s future was balanced on a knife edge. As the rebels closed in on London, some of his greatest military leaders – men such as the Earl of Suffolk and Lord Bergavenny – considered which side to back. If they’d thrown their weight behind the insurrection, royal forces could have been outnumbered and overpowered. Fortunately for the king, the captains couldn’t quite bring themselves to defect. Henry mobilised enough active allies to crush the rebels, after which their leaders were put to death.
He had narrowly averted catastrophe – but this was barely cause for celebration. More than a decade after his great triumph over Richard III at the battle of Bosworth in August 1485, Henry VII was still at war with his own subjects.
Henry’s army defeats Richard III at the battle of Bosworth, as imagined in a 19th-century painting | Credit: Getty Images
Grand union
How had it come to this? After all, victory at Bosworth should have provided the firmest of foundations for Henry’s royal tenure. Richard III was dead, and his most committed followers had been killed or captured. Then, in the first few months of his reign, Henry pulled off the masterstroke of marrying Richard’s niece, Elizabeth of York, thus binding many of her previously hostile Yorkist supporters to her new husband’s Lancastrian regime.
It was a positive start to the Tudor administration, and one on which Henry attempted to build, aiming to ensure a trouble-free period in which he could learn how to be king.
More than a decade after his triumph at the battle of Bosworth in 1485, Henry VII was still at war with his own subjects
His investment in stability was underlined in his first parliament in November 1485, which restored status and wealth to his Lancastrian allies attainted for treason under Richard and his older brother Edward IV, and which punished his predecessor’s followers. This he achieved by backdating the start of his reign to the day before Bosworth – thus making traitors of Richard’s supporters at the battle, and restoring the badge of loyalty to his own.
This was just one of many examples that, even by the end of 1485, demonstrated Henry’s willingness to exploit information, public spectacle and legalistic tricks to uphold his power. His reputation for parsimony and avarice also became established quickly: he gifted titles and lands to relatives and allies, but largely held onto the crown’s resources. Even Henry’s saviour at Bosworth, Sir William Stanley, had to be content with gifts and offices, not a peerage.
A copy of Henry’s first act of parliament with the new king depicted with advisors in the illuminated letter H. He worked to head off rebellion through legalistic tricks and by building support across factions | Credit: Getty Images
During this period, Henry relied on trusted pre-Bosworth friends who were already in the royal council and household to form the core of Tudor rule. The best of his foot soldiers formed the new bodyguard, the Yeomen of the Guard. The king himself was from a Welsh family, and followers such as Dawyd ap Howel and Cadwaladr John constituted a strong Welsh presence among his personal attendants. But Henry knew that only by expanding this pool could he foster a regime in which anyone could thrive – so long as they proved their loyalty.
He soon put this tactic into practice. On his first royal tour of the country in spring 1486, he was accompanied by courtiers from different backgrounds. Pageants of welcome proclaimed his ancestry and right. At Worcester, an actor playing Henry VI emphasised how the new King Henry had inherited that former monarch’s merciful rule. Brennius and Ebraucus, the mythical founders of Bristol and York, respectively, proclaimed that Henry had been sent from God to restore prosperity.
- Read more | Married three times by the age of 15: Margaret Beaufort, the woman who birthed the Tudor Dynasty
Heir trigger
Despite his initial success, Henry knew that, to fully cement his Tudor regime, he had to produce a male heir with indisputable royal ancestry. And less than a year after he took the throne, on 20 September 1486, his son Arthur was born. The christening celebrations linked the infant prince with the legendary British ruler after whom he had been named, promising ideal kingship under a real Arthur in future.
Henry, Prince of Wales, painted by a Flemish artist c1509 – the year his father died and he succeeded to the throne as Henry VIII | Credit: Alamy
The Tudor heir’s birth offered the promise of an enduring Tudor dynasty. But the king’s enemies – those Yorkists who would have liked to see that dynasty wiped from the face of the Earth – hadn’t gone away. Henry’s foes knew that the longer he ruled unopposed, the more thoroughly his subjects would accept him. So they ramped up their plotting – and that plotting would dog Henry for the rest of his reign.
The mastermind behind these schemes to unseat the new Tudor king was Richard III’s sister Margaret, Dowager Duchess of Burgundy. According to the Italian historian Polydore Vergil, writing the following century, she “pursued Henry with insatiable hatred and with fiery wrath… employing every scheme which might harm him”.
Timeline
Henry VII's rollercoaster life
28 January 1457: Henry VII is born in Pembroke Castle, Wales, the son of Edmund Tudor and 13-year-old Margaret Beaufort 22 August 1485: Henry defeats Richard III at the battle of Bosworth and seizes the English crown 20 September 1486: A son and heir, Arthur, is born to Henry and his wife, Elizabeth of York 16 June 1487: Henry's army defeats the forces behind the boy claiming to be Edward, Earl of Warwick (actually an imposter, Lambert Simnel) at the battle of Stoke Field May–June 1497: A rebel army advances on London from south-west England, finally being defeated at the battle of Blackheath November 1499: Following failed attempts to free the imposter Perkin Warbeck and Edward, Earl of Warwick from the Tower of London, Henry has them both executed 2 April 1502: Prince Arthur dies, probably from the sweating sickness. Ten-year-old Prince Henry is now heir to the throne 11 February 1503: Henry's queen, Elizabeth of York, dies shortly after giving birth to a daughter. The king is distraught 21 April 1509: Henry VII dies of tuberculosis at Richmond Palace, aged 52. His son succeeds as Henry VIII
Margaret persuaded a cadre of Yorkist nobles who’d resolutely refused to accept the outcome of Bosworth to back the last legitimate Yorkist prince: Edward, Earl of Warwick, Richard III’s nephew. The real Warwick was imprisoned in the Tower of London, so the rebels produced a pretender to impersonate him. Lambert Simnel appeared in Dublin at the start of 1487, claiming to have escaped from Henry’s clutches. There he was crowned as Edward VI of England – making Henry “deeply disturbed”, according to Vergil. In June, a large Irish and mercenary army supporting Simnel’s claim, bankrolled by Margaret, invaded northern England.
The king responded by offering pardons to those near the cusp of rebellion, averting widespread northern insurrection – but not the need to fight. Defeating the invaders in a bloody battle at Stoke Field in Nottinghamshire on 16 June 1487, Henry was encouraged by the turnout of loyal lords and knights to believe that his policies were working. (Simnel was pardoned and put to work in the royal household.) But it was to be far from the last challenge to his reign.
An invasion attempt by supporters of the boy claiming to be Edward, Earl of Warwick – actually Lambert Simnel – is defeated at Stoke Field in 1487 | Credit: Getty Images
Northern uproar
Henry’s knowledge of government and diplomacy developed rapidly – because it had to. In 1489, onerous tax demands sparked protests in northern England, where Richard III had enjoyed widespread support, and the Earl of Northumberland was murdered near Thirsk while trying to collect these levies. To tackle the uprising, Henry turned to a former Yorkist, Thomas Howard, who had been attainted following Bosworth. Restoring Howard’s title as Earl of Surrey, Henry sent him to quash the rebellion and then run the north of England as his lieutenant there.
To rekindle a sense of collaboration across his kingdom, in November 1489 Henry made his son, Arthur, Prince of Wales; fortuitously, his daughter, Margaret, was born on the eve of the investiture at Westminster. Might this signal a change of fortunes for the king? Henry hoped so and, with renewed optimism, drove forward his efforts to end international sponsorship of the Yorkist rebels. As it turned out, his forays into foreign diplomacy would backfire.
Henry’s overseas policy involved forging alliances with the Spanish monarchs and Maximilian Habsburg, ruler of the Netherlands, alienating the French. France’s king Charles VIII responded by increasing his support for English conspirators. And in December 1491, those plotters hatched a new scheme: a boy appeared in Ireland claiming to be Richard, Duke of York, youngest of the princes in the Tower. (The pretender was actually a Flemish lad named Perkin Warbeck.) His claim was backed by Margaret of Burgundy, who ranted to European rulers such as Isabella of Castile that they should not “allow the throne of England to be tyrannically usurped by a supremely wicked enemy”.
A 15th-century portrait of Margaret of Burgundy, sister of Richard III, who backed multiple attempts to oust Henry | Credit: Alamy
According to Vergil, the apparent return of Prince Richard “was not merely believed by the common people but [by] many important men”. Henry became desperate to prove that the claimant was an imposter.
In October 1492, in a bid to end French support for English rebels, Henry launched an invasion of France. After besieging Boulogne, he forced the French to come to terms with him. But, in doing so, he offended Maximilian, who became another champion for Warbeck.
A king in the making
As the threat posed by ‘Richard’ and his backers grew, Henry retreated to the Midlands and moved troops to Ireland to reinforce his tenuous control. Investigators found that support for a Yorkist restoration was growing in the households of Henry’s aristocratic allies. In response, the king decided to boost the profile of his own heir. He had Prince Arthur, still aged only six, installed as a regional leader at Ludlow in the Welsh Marches, to begin intensive training for kingship. Making Henry’s three-year-old second son, also Henry, Duke of York at the end of 1494 reminded everyone that there was only one legitimate holder of that title.
Henry also unleashed a wave of arrests to shatter Warbeck’s support network. One of the hundreds tried was Henry’s former ally Sir William Stanley. More than £9,000 in coin was found at Stanley’s castle of Holt – an amount that could have sustained an army of thousands for weeks. His execution in February 1495 highlighted Henry’s failure to overcome Yorkist sympathies. Around this time, a Florentine merchant in London reported that the king was “rather feared than loved… if fortune allowed some lord of the blood royal to rise [then] his people would abandon him”.
A portrait of Maximilian Habsburg by Albrecht Dürer. Henry managed to alienate this powerful European ruler | Credit: Getty Images
Meanwhile, Warbeck’s supporters continued to harry the king. An attempt to invade England in July 1495, backed by Maximilian, was a failure and he was forced to retreat to Ireland. But by the end of that year Warbeck had appeared in Scotland, cosying up to James IV. In response, Henry levied more taxes to fund an army there – triggering the south-western uprising that culminated in the battle of Blackheath.
Still Warbeck wouldn’t go away. After another failed invasion via Northumberland in September 1496, the following autumn his forces sailed to Cornwall. Recruiting many who’d taken part in the earlier insurrection, he besieged Exeter – but his men melted away as loyal forces approached. Finally, the pretender was captured and interviewed on 5 October. Failing to identify lords who had known Prince Richard before 1483, Warbeck confessed. Henry spared his life and triumphantly broadcast news of the conspiracy’s collapse across Europe.
Safe, but not loved
Henry had survived, but he was far from unscathed. The Spanish ambassador noted that “the king looks old for his years, but young for the sorrowful life he has led”. He was safe on the throne, but not loved. When, at the start of 1499, a Cambridge student named Ralph Wilford impersonated the Earl of Warwick, Henry ruthlessly executed him. The shock of this new threat apparently turned the king’s hair white.
Ludlow Castle, in the volatile Welsh Marches, where Henry’s son Arthur was sent at the tender age of six to begin intensive training in kingship | Credit: Getty Images
Perhaps unsurprisingly after so many challenges to his reign, Henry became increasingly paranoid, and his rule harsher. In 1499, he introduced a new court, the Council Learned in the Law, strengthening his authority over land and income. That summer, too, an attempt to free Warbeck and Warwick from the Tower was thwarted. Both were tried and executed.
The long-awaited wedding of Prince Arthur to his Spanish bride, Catherine of Aragon, in November 1501 promised a chance for Henry’s reign to be shaped afresh. Pageants, banquets, jousts and discussions reinforced the alliance. As the newlyweds headed back to Ludlow for Christmas, the king might have looked to the future with renewed confidence.
When a Cambridge student impersonated the Earl of Warwick, the shock of this new threat turned the king’s hair white
If so, it was short-lived. The following Easter, Arthur died suddenly, possibly from the mysterious, virulent sweating sickness that had swept through Europe since 1485.
The future of Tudor rule now rested with 10-year-old Prince Henry, born five years after his brother. His preparation for kingship had to be achieved quickly – and without the support of his mother. In February 1503, Elizabeth of York died shortly after giving birth, along with her infant daughter. The king’s “heavy and dolorous” reaction saw him isolated for several days. For the rest of his life, he suffered episodes of severe respiratory illness, spiking around the anniversary of Elizabeth’s death.
A copy of a c1500 portrait of Elizabeth of York, Henry’s queen – and, crucially, daughter of King Edward IV and niece of Richard III | Credit: Alamy
Henry responded to that triple tragedy by doubling down on his efforts to consolidate lasting Tudor power. And in June 1503, Prince Henry’s betrothal to his brother’s widow, Catherine, was confirmed in a new Anglo-Spanish treaty.
Over the first 18 year years of his reign, with threats emerging all too frequently, Henry had held fast to his longstanding friendships, relying on those stalwarts for support and advice. As his confidants began to perish, though, he became increasingly reluctant to delegate.
From 1504, the king utilised the crown’s inherent rights – the royal prerogative – to inflate payments for his goodwill. Royal servants were squeezed hard: the justice Robert Rede, for example, had to pay a £300 bribe to renew his post. Henry put the bureaucrats Richard Empson and Edmund Dudley in charge of this clampdown. Several years of grinding harshness followed as Empson and Dudley filled the royal coffers with fines extracted by legal tricks and informers. Henry aimed to “keep all Englishmen obedient through fear”, suggested Vergil.
Generational strife
Young Henry’s safety now became the king’s priority, and the prince’s independence was curtailed. There was little confidence that Tudor rule would continue should the king die before his heir reached adulthood.
Henry VII (centre) is shown with his advisors Richard Empson (left) and Edmund Dudley, who helped him squeeze money out of his subjects | Credit: Alamy
The spectre of civil unrest haunted Henry VII for most of his 24 years on the throne – and had barely subsided when he did perish, at Richmond Palace on 21 April 1509, of tuberculosis. His 17-year-old son, now Henry VIII, knew that he must act quickly to head off yet another rebellion, so his father’s death was concealed for two days to enable the arrest of Empson and Dudley – handy scapegoats for the first Tudor king’s oppressive final years. Young Henry decried his father’s agents as “the most savage extortioners who eagerly plundered all secular and ecclesiastical wealth”. In doing so, he cannily plugged into the public mood.
Henry’s reign had started with an air of great promise before descending into rebellion and reaction
“Heaven smiles, Earth rejoices; all is milk and honey and nectar.” This famous statement, written by the Tudor courtier Lord Mountjoy, captures the excitement generated by the accession of a vigorous young king – one who promised a clean, bold break from the penny-pinching and paranoia that preceded him.
But should we judge Henry VII’s reign so harshly? It had started with an air of great promise before descending into rebellion and reaction. True, it had been increasingly choked by a suffocating cloud of suspicion and austerity. Yet it’s also worth remembering that Henry VIII was able to ascend the throne only because his father had navigated a period of extreme peril – one in which enemies seemingly lurked around every corner. For all his missteps, Henry VII was a great survivor – and for that, at least, his famous son had cause to be thankful.
Sean Cunningham is head of collections for medieval, early modern and legal records at the National Archives. His books include Henry VII: Treason and Trust (Penguin Monarchs, 2026)
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This article was first published in the December 2026 issue of HistoryExtra Magazine
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