Wales, 7 August 1485. As the sun lowered beneath the horizon across the Milford estuary, a flotilla of ships drifted across the mouth of the Haven. It had been a week since the fleet had sailed from the shelter of the Seine at Honfleur, but the ships had made fast progress in the balmy August weather. Onboard, the soldiers waited. They included a rabble of 2,000 Breton and French soldiers (many only recently released from prison and, according to the chronicler Commynes, “the worst sort… raised out of the refuse of the people”). There were also a thousand Scottish troops and 400 Englishmen, whose last sight of the country had been two years previously, when they had fled in fear of their lives.


The ships entered the mouth of the estuary where, looking leftwards, the dark red sandstone cliffs, several hundred feet in height and impossible to scale, gave way to a small cove hiddenrom sight from the cliffs above. High tide had passed an hour previously, enabling the ships to creep silently to the edge of the narrow shoreline, allowing the troops to disembark. Their arrival stirred no one. The waters soon clouded with sand as the men began to heave cannon, guns and ordnance from the boats, leading horses from the ships and onto land.

From one of the boats stepped a 28-year-old man. Pale and slender, above average height with shoulder-length brown hair, he had a long face with a red wart just above his chin. Yet his most noticeable feature to those who met him was his small blue eyes, which gave out the impression of energy and liveliness whenever he spoke.

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Stepping from his boat, the man took a few steps forward on land upon which he had last set foot 14 years before. Kneeling down in the sand, he took his finger and drew a sign of the cross, which he then kissed. Then, holding up his hands to the skies, he uttered words from the first line from the 43rd Psalm: “Judge and revenge my cause O Lord,” which the soldiers now began to sing. As the words of the psalm echoed around Mill Bay in the darkening evening, one line in particular must have stood out above all others: “O deliver me from the deceitful and unjust man.”

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Moment of reckoning

The journey across Wales to win a kingdom had only just begun. For Henry Tudor, his arrival to claim the crown of England was the end of a journey that had lasted his whole life. The moment of reckoning had arrived.

The remarkable rise of the Tudors to prominence is shrouded in fable. Long before Henry Tudor’s landing in 1485, the family had nearly driven itself into annihilation due to their support of Owain Glyndwr’s disastrous rebellion in 1400. It would take a scandalous affair to trigger a remarkable turnaround in the Tudors’ fortunes.

Owen Tudor was a household servant in Henry V’s court. After the king’s premature death, his widowed queen, Katherine of Valois, took a shine to the handsome Welsh page, supposedly after he had drunkenly fallen into her lap dancing at a ball. Their illicit union, later formalised by a secret marriage, produced several children, including Edmund and Jasper Tudor, recognised by Henry VI as his half-brothers when he created them the earls of Richmond and Pembroke.

Edmund had his own ambitions for self-enrichment: his means would be marriage, namely to the wealthiest heiress in the land, Margaret Beaufort, the sole inheritor of the Beaufort family fortune, who had her own claim to the throne. Margaret was just a child, but when it came to marriage, land took precedence over love for Edmund. Aged just 12, Margaret found herself pregnant. Edmund, however, would not live to see the birth of his heir.

Although Edmund Tudor is reported to have died of the plague, this obscures the fact that he had been recently arrested by adherents of the king’s rival, Richard, Duke of York; his treatment in prison, many suspected, hastened his death. Already divisions between the houses of Lancaster and York had been exposed to full glare at the first battle of St Albans in 1455, where Jasper Tudor himself witnessed the Lancastrian king Henry VI being injured in the fight. Civil war would soon erupt as the Duke of York claimed the throne for himself.

With Edmund’s death, Jasper Tudor would assume the mantle of the head of the family. He had Margaret swiftly married to Henry Stafford, the second son of the wealthy Duke of Buckingham. But any newfound stability was to be short-lived. Despite an attempt at reconciliation, factionalism between the Lancastrian court and York’s supporters erupted into open warfare in the late 1450s and into 1460, when the Yorkists secured a crushing victory at Northampton, capturing Henry VI. York was declared Henry’s successor, only for a dramatic reversal in fortune when the duke was executed after the battle of Wakefield in December 1460. York’s son and heir, Edward, Earl of March, wreaked his revenge two months later when, at the battle of Mortimer’s Cross in early 1461, he routed the Lancastrian forces, killing 3,000 Welshmen. One of the victims was an elderly Owen Tudor, who was executed at the market cross in Hereford, his last words reportedly being “That head shall lie on the stock that was wont to lie on Queen Katherine’s lap”. Jasper was forced to flee, promising to avenge his father’s death “with the might of the Lord.”

Vengeance would be a long time coming. Edward’s crushing victory at the battle of Towton a month later heralded a decade of Yorkist rule, as Edward acceded to the throne as Edward IV. In exile first in Wales and later France, Jasper was stripped of his earldom, while his young nephew Henry was placed in the charge of the new Earl of Pembroke, William Herbert, where he was brought up at Raglan Castle, under the care of Herbert’s wife, Anne. His mother, Margaret, paid occasional visits to her son. However, mother and son weren’t reunited until 1470, when the defection of Warwick ‘the Kingmaker’ forced Edward IV from power and returned Henry VI to the throne. Margaret could now pay for a bow and sheaves of arrows to keep Henry amused. She even arranged for an audience with Henry VI, who is reported to have foretold that Henry Tudor would one day inherit the kingdom.

Jasper was restored to his earldom and given extensive powers under the restored Lancastrian regime, but it was not to last. In March 1471, Edward IV launched a remarkable comeback, returning from exile in Holland. Within the space of a month, two critical battles at Barnet and Tewkesbury resulted in the deaths of Warwick, Margaret Beaufort’s husband Stafford and Henry VI’s son Prince Edward, shortly followed by Henry VI’s own suspicious end in the Tower. The Lancastrian dynasty had run into the sand. Through the brutal consequences of war, Henry Tudor was rapidly becoming one of the last remaining members of the royal family, although his claim to the throne was hardly taken seriously at the time.

Blown off course

After the crushing defeat of the Lancastrian forces at Tewkesbury, Jasper had no choice but to flee into exile again. This time, sailing in a small boat from Tenby bound for French shores where he hoped to enlist the support of Louis XI, he took his 14-year-old nephew Henry with him. Yet when a storm blew them off course, they found themselves washed up on the shores of Le Conquet in neighbouring Brittany. At the time, Brittany was an independent duchy separate to France and relations between the two were openly hostile, perfectly understandable given French ambitions to unite the two countries.

The Breton ruler, Duke Francis II, recognising the value of the Tudors as diplomatic pawns, welcomed Jasper and Henry to his court. Francis understood that these new arrivals could be used to bargain with Edward IV, who was desperate to have both returned to England. He remained determined to keep both under close supervision, separating uncle and nephew, with Henry sent to the isolated Tour d’Elven, where he was imprisoned on the sixth floor of its keep. Henry’s exile in Brittany over the next 14 years would be spent as a prisoner, albeit with household expenses totalling £2,000, along with £620 for his own personal use.

Edward IV made repeated failed attempts to entice Francis to hand over the Tudors. In 1476, he persuaded the duke that he intended for Henry to marry his daughter Elizabeth and requested his return. Francis fell for the trap and Henry was taken to St Malo, ready to be boarded onto a ship to transport him back to England. But Henry feigned illness and, in the ensuing delay, managed to escape into sanctuary in the town.

Edward IV’s death in April 1483 marked a turning point in Henry’s fortunes. Following the mysterious disappearance of Edward V and his brother in the summer of 1483, together with Richard III’s seizing of the crown, a massive rebellion led by the Duke of Buckingham broke out in October 1483. Spurred on by his mother, Margaret Beaufort, who appears to have been strongly involved with the organisation of the rebellion, Henry decided to sail to the English coast with a fleet of Breton ships in the hope of invading. But the rebellion collapsed and, with Buckingham’s execution, Henry had no option but to return to Brittany.

Silver linings

Henry’s aborted attempt to claim the crown may have ended in disaster, but its consequences were to prove highly advantageous. Hundreds of exiles fleeing from England soon arrived at Henry’s ‘court’, many of whom were former household men of Edward IV, distraught at Richard’s usurpation. They had now switched sides, backing the Lancastrian Henry Tudor. Henry also pledged an oath on Christmas Day 1483 to marry Elizabeth of York, Edward IV’s eldest daughter, thereby uniting the houses of Lancaster and York.

But Henry’s time in Brittany was soon to be cut short. When Richard offered to provide a force of several thousand archers to aid Brittany in their conflict with France, in return Henry and Jasper were to be arrested. Henry was tipped off about the plan with just hours to spare and managed to flee to France where he was received by the French court of Charles VIII. As a pawn in the diplomatic chessboard played out between France, Brittany and England, Henry’s arrival was a gift for the French regime, who agreed to equip Henry with money, ships and mercenaries “of the worst sort” to launch an attack on Richard. At the last moment, though, they held back on their promises of funding, forcing Henry to borrow from brokers in Paris. He set sail with his army on 1 August 1485.

Richard III was reportedly “overjoyed” at news of Henry’s landing. Yet, as Henry’s march along the coastline of Wales went unhindered, Richard grew nervous, becoming suspicious of the involvement of Henry’s step-father, Thomas Stanley (who had become Margaret Beaufort’s third husband), and his brother Sir William Stanley in the lack of resistance to Henry’s growing band of men as he travelled through north Wales and to the gates of Shrewsbury. The key defections of Welsh landowner Sir Rhys ap Thomas and Sir Gilbert Talbot provided Henry with the momentum he needed to push forward towards London, planning to march down Watling Street, the current-day A5.

Richard had spent the summer at Nottingham, waiting to see where Henry might land, but now he hurried down to Leicester where he amassed a force of some 15,000 men – at the time, one of the largest armies ever assembled on one side. On 21 August, both armies drew closer, camping the night overlooking the marshy terrain known as ‘Redemore’ near the villages of Dadlington, Stoke Golding and Upton.

Still, Henry could not be sure of the Stanleys’ final support at Bosworth. Suspecting treachery, Richard had kept Thomas Stanley’s son, George Lord Strange, imprisoned as a hostage to ensure his father’s good behaviour. Henry held a clandestine meeting with both brothers the night before, and when morning came, Stanley refused to march his forces into line, preferring to remain upon the brow of the surrounding hills, between both armies.

Richard, meanwhile, had slept badly, supposedly haunted by nightmares. He woke to find that his camp was unprepared to hear mass or eat breakfast. As both sides lined up for battle in the early hours of 22 August, it was clear that Richard’s army was vastly superior, with his “countless multitude” of men. In contrast, Henry had at best 5,000 men, of which his French mercenaries had to be kept apart from his native soldiers, for fear of them falling out.

Henry’s vanguard was led by the Earl of Oxford, the Lancastrian commander who had managed to escape imprisonment to join Henry in France. Oxford’s expertise saw Richard’s vanguard routed and the death of its commander, the elderly Duke of Norfolk. By now, Richard had begun to realise that many on his own side, particularly those led by the Earl of Northumberland in his rearguard, were standing still, refusing to fight. He was offered the chance to flee yet refused, preferring to fight to the death.

Spotting Henry at the back of the battlefield, surrounded only by a small band of soldiers, Richard charged on horseback towards its ranks. After unhorsing Sir John Cheney, at 6ft 8ins one of the tallest soldiers of the day, Richard’s men managed to kill Henry’s standard-bearer, Sir William Brandon, while Richard’s own standard-bearer, Sir Percival Thirlwall, had both his legs hacked away beneath him.

With Henry fearing imminent death, the sudden charge of Sir William Stanley’s 3,000 men saw Richard swept into a nearby marsh, where he was killed as the blows of the halberds of Henry’s Welsh troops rained down on him. Thanks to Richard’s remains having recently – and finally – been discovered under a Leicester car park, we know that the king suffered massive trauma to the head, including one wound which cut clean through the skull and into his brain. With the king dead, after two bloody hours the battle was over: on the nearby ‘Crown Hill’, Henry was proclaimed king by Thomas Stanley.

Two months later, Henry was officially crowned Henry VII at Westminster Abbey. The following January, he married Elizabeth of York, thereby fulfilling his promise to unite the houses of Lancaster and York. After decades of uncertainty and exile, the Tudor dynasty was finally born.

Three notable figures in Henry VII’s life

Jasper Tudor

The loyal uncle of Henry Tudor – it was through Jasper’s care and devotion that the Tudor dynasty was born. The second son of Owen Tudor, Jasper found himself embroiled in the civil wars as he defended his half-brother Henry VI. When Henry lost the throne, Jasper went into exile, taking his nephew with him. He remained a constant presence in Henry Tudor’s life, his loyalty rewarded after Bosworth with the dukedom of Bedford.

John de Vere, Earl of Oxford

A stalwart Lancastrian, whose father and brother had been executed by the Yorkists, the Earl of Oxford came to prominence at the battle of Barnet in 1471 when, on the cusp of victory, his troops were defeated by Edward IV after they became confused in the mist and began attacking their own side. Oxford fled, only to reappear three years later when he seized St Michael’s Mount. In 1484, he joined Henry in exile in France. Making the journey to Bosworth, Oxford was placed in command of Henry’s vanguard. His military knowledge – in particular manoeuvring his troops to ensure that the sun and the wind were against Richard’s forces – may have proved critical in winning the battle.

Margaret Beaufort

Henry Tudor’s “dearest and most entirely beloved mother”, Margaret was barely a teenager when she gave birth to her only son. Suspected to be one of the driving forces behind Buckingham’s rebellion, she encouraged her son to invade, sending money and support. After Henry’s assumption of power, Margaret became one of the most important figures at court. She died two months after her son.

Chris Skidmore is an author, historian, MP for Kingswood and vice-chairman of the All-Party Group on History and Archives


This article was first published in the June 2013 issue of BBC History Magazine