Bosworth Field: How Henry VII Won the Crown and Began the Tudor Dynasty

The morning of August 22, 1485, was not just the dawn of a new day, but the violent birth of England's most famous royal house. On a muddy field near Market Bosworth, two armies faced each other, representing the final, bloody spasm of the Wars of the Roses. On one side stood Richard III, the last Plantagenet king, fighting desperately to secure a crown tainted by rumour and suspicion. On the other, a relatively unknown exile, Henry Tudor, Earl of Richmond, who carried the hopes of the Lancastrian cause and, crucially, the ambition to forge a new dynasty. The Battle of Bosworth Field was more than just a skirmish; it was the hinge upon which English history turned, catapulting Henry VII onto the throne and ushering in the magnificent, tumultuous age of the Tudors.

The Road to Bosworth: Henry Tudor's Precarious Claim

Henry Tudor's claim to the English throne was, by conventional standards, tenuous at best. Born in 1457, he was the son of Edmund Tudor and Margaret Beaufort. His royal lineage stemmed entirely from his mother, a direct descendant of John of Gaunt, but through an illegitimate line that had been legitimized only with the caveat that it could not inherit the crown. Yet, the chaos of the Wars of the Roses meant that any viable alternative to the reigning monarch could gain traction.

Following the Yorkist victory at Tewkesbury in 1471, the young Henry spent fourteen years in exile in Brittany and France, constantly under threat of extradition or assassination. This period of enforced political apprenticeship proved invaluable, teaching him patience, diplomacy, and the necessity of securing powerful alliances. His opportunity arose when Richard III’s hold on power weakened following the mysterious disappearance of the Princes in the Tower and widespread discontent among the nobility.

The Invasion: Landing at Milford Haven

In August 1485, Henry launched his invasion, landing at Milford Haven in Wales. This location was strategic; Henry had Welsh ancestry (through his father’s family, the Tudors of Penmynydd), and he hoped to capitalize on local loyalty and resentment towards Richard III’s English rule. His initial force was small—perhaps only 2,000 men, largely French mercenaries and English exiles. As he marched east, he needed to gather momentum and, more importantly, secure the support of powerful English magnates.

“For though the Earl of Richmond had but a small number of men, yet he had the hearts of many more, who wished him well, and were ready to join him upon the first opportunity.”
— Polydore Vergil, Anglica Historia (Historian commissioned by Henry VII)

The Critical Role of the Stanleys

The true key to the Battle of Bosworth lay not in the strength of Henry’s army or Richard’s, but in the calculated neutrality of the Stanley family. Lord Thomas Stanley and his brother, Sir William Stanley, commanded significant forces—perhaps 6,000 men—and positioned themselves strategically between the two main armies. Thomas Stanley was Henry Tudor’s stepfather, but he was also understandably cautious, as Richard III held his son, Lord Strange, hostage.

Richard III, aware of the Stanleys’ divided loyalties, had demanded their immediate commitment. Their refusal to engage immediately was a deliberate tactic, designed to observe the flow of battle and commit their forces only when the outcome was certain, thus ensuring they backed the winner and protected their vast estates and influence.

Richard III's Fatal Confidence

Richard III arrived at Bosworth with a larger, better-equipped army, estimated at around 10,000 men. He was a seasoned military commander, having proven his prowess at battles like Tewkesbury. He positioned his forces on Ambion Hill, a strong defensive position. However, Richard’s confidence was undermined by the palpable tension and distrust within his own ranks, particularly concerning the Duke of Northumberland, who commanded a large contingent but remained suspiciously passive.

The battle began with a volley of arrows, followed by a fierce clash between the main bodies of the two armies. Henry’s forces, though outnumbered, fought with the desperation of men who knew failure meant execution.

The Decisive Moment: Richard's Charge

As the battle raged, Richard, observing that the main fighting was inconclusive and seeing Henry Tudor positioned relatively exposed behind his lines, made a desperate, high-stakes decision. He decided to bypass the main engagement and launch a direct cavalry charge aimed solely at killing Henry Tudor, believing that eliminating the claimant would instantly end the rebellion.

This was a moment of extraordinary personal courage, but also military recklessness. Richard, recognizable by his golden crown worn over his helmet, cut a swathe through Henry’s retainers. He reportedly killed Henry’s standard-bearer, Sir William Brandon, and unhorsed the formidable John Cheyne.

Just as Richard closed in on Henry, Sir William Stanley, who had been watching from the sidelines, finally made his move. Stanley’s cavalry swept down, crashing into Richard’s exposed flank.

“The King [Richard] was slain in the very middle of his enemies, fighting manfully in the thickest press of his adversaries.”
— Bernard André, Historia Regis Henrici Septimi (Henry VII’s official historian)

Overwhelmed and surrounded, Richard III was killed. His body was stripped and carried back to Leicester, ignominiously slung over a horse. The discovery of his remains centuries later confirmed the violent end of the last Plantagenet king.

The Aftermath and the Birth of Tudor England

With Richard dead, the battle instantly ceased. The crown, which had fallen from Richard’s helmet during the charge, was reportedly retrieved from a hawthorn bush and placed upon Henry Tudor’s head by Sir William Stanley on the battlefield itself. This symbolic act instantly legitimized Henry as King Henry VII.

The immediate consequences of Bosworth were profound:

• Dynastic Shift: The Tudor dynasty began, lasting 118 years and producing five monarchs.
• End of the Wars of the Roses: Henry VII’s subsequent marriage to Elizabeth of York unified the warring houses (symbolized by the Tudor Rose).
• Consolidation of Power: Henry immediately backdated his reign to August 21, 1485 (the day before the battle), ensuring that all those who fought against him at Bosworth were legally traitors.
• New Administration: Henry relied heavily on loyal, skilled administrators (often from the gentry class rather than the old nobility) to rebuild the royal finances and centralize power.

Bosworth Field was not the largest battle of the era, but its impact was unparalleled. Henry VII, the unlikely victor, proved to be a cautious, intelligent, and highly effective ruler. He spent the next two decades meticulously securing his throne, suppressing rebellions, and filling the royal coffers, laying the stable financial and political foundation upon which his son, Henry VIII, and granddaughter, Elizabeth I, would build their legendary reigns.

The victory at Bosworth was a testament to Henry’s tenacity, Margaret Beaufort’s political maneuvering, and the treachery of the Stanleys. It closed the chapter on medieval England and opened the door to the Renaissance, reform, and the glorious, complex history of the Tudors. To understand the Tudors, one must first understand the desperate fight for survival that took place on that fateful Leicestershire field.