August 22nd marked the anniversary of the Battle of Bosworth, one of the more pivotal moments in English history. To some, it’s remarkable for ending the “Wars of the Roses” (a debatable point), while to others it’s memorable for being the last time an English monarch lost their life on the battlefield and beginning the Tudor dynasty. So, let’s get into it.

The battle took place on August 22, 1485, though it was then known as the Battle of Redemore and took place close to the towns of Dadlington and Stoke Golding. At its start, Richard III wore the crown, and by its end that dignity had been taken by Henry Tudor, soon to be proclaimed Henry VII. Richard’s body was buried nearby, not to be discovered until 2012 under a carpark/parking lot. Henry, on the other hand, is a direct ancestor for every subsequent English monarch and, starting in 1513, every Scottish one, too.

All good battles show an unexpected victory and, whether you’re a Ricardian or a Tudor fan, this battle was certainly an upset. Richard may have only sat on the throne for a little over two years in August 1485, but he was a seasoned military commander who had been fighting since he was an adolescent. In contrast, Henry spent his life in exile abroad – he learned his sword fighting like any nobleman, but he was untried in actual combat.

The events leading up to the battle have been captured a few times elsewhere – I would direct you to this post on Elizabeth of York, this post on Margaret Beaufort or this post on Elizabeth Woodville.

Henry landed in Wales on August 7, six days after setting sail from Harfleur with a merry band of exiles and French mercenaries. The exact size of his army is debated, but is traditionally given as roughly 5,000, many of whom were there thanks to the financial backing of the French. Richard had done little to ingratiate himself with France over the years, whereas Henry was in fact one-quarter French thanks to his paternal grandmother, Katherine of Valois. He was a descendant of Charles VI and a cousin to the adolescent Charles VIII and his sister/regent, the Duchess of Bourbon, thus predisposing them to favor his claim.

That, and the House of York had traditionally allied itself with Burgundy, an off and on thorn in France’s side. Richard’s sister, Margaret of York, was the widow of Duke Charles of Burgundy and was serving as regent for her stepdaughter’s son, Philip of Austria, as of when Bosworth took place.

As for the English who defied their king – loyal Lancastrians were more than happy topple a Yorkist monarch, while Yorkists who believed Richard has usurped the throne from his nephew, Edward V, had little interest in his continuation. Even so, Richard was well-prepared for this invasion – the threat of it had been mounting since the autumn of 1483 and this particular wave of it had been on his radar since early summer. Richard had at his disposal an army roughly three times the size of Henry’s, in addition to an astonishing 140 cannons (astonishing for a 15th century battle, that is).

News of Henry’s landing reached Richard four days later, at which point he sounded the alarm for his men to gather. Among them were the Stanley brothers – Thomas and William – the elder of whom was married to none other than Henry’s mother, Margaret Beaufort. Ostensibly, both men were loyal Yorkists and had been for years, but it was well-known Margaret’s loyalty was to her son and she had actively plotted with Henry Stafford, Duke of Buckingham in 1483, a fiasco that ended in the Duke’s death and her house arrest.

Richard first ordered the Stanleys to raise men in his name, however when news reached him that Henry was marching unopposed, he ordered that they join him in person. He was by then well-aware that both men had been in contact with Henry thanks to the presence of Thomas’s eldest son, George, Lord Strange, at his court. When Thomas plead illness, Richard made it clear that he was holding George had a hostage and his fate was dependent on Thomas’s good behavior.

Henry was in fact marching freely, traveling some 200 miles east towards London, while Richard and his army prepared to intercept them before they reached the capital. On August 20, Richard and the Earl of Northumberland reached Leicester, joining the stalwart John Howard, Duke of Norfolk. They settled on Ambion Hill and set up camp. The Stanleys, meanwhile, were traveling ahead of Henry and twice met him secretly as he slowly crossed Staffordshire. They eventually set up camp at Dadlington, while Henry and his men based themselves northwest of them.

On the morning August 22, Richard’s face was described by the Croyland Chronicle as more “livid and ghastly” than usual thanks to a poor night’s sleep. His army arranged itself along the hilltop, with Richard holding the center, Northumberland commanding the left flank and Norfolk the right. Henry, meanwhile, was a novice and while he was the nominal head of his army, actual operations were led by Lancastrian loyalist John de Vere, Earl of Oxford, who commanded the vanguard against Norfolk. Instead, Henry remained in the rear, surrounded by bodyguards.

The Tudor army made the first move, while Richard sent an order to Thomas Stanley to meet them on the battlefield immediately or he would order George’s execution. Thomas responded, “Sire, I have other sons.” Livid, Richard in fact ordered the younger man’s beheading, but his soldiers held him off on the grounds that the battle was imminent and could wait until later. Henry, too, had sent word to Thomas, but Thomas answered he would come later – in other words, he was standing on the sidelines, waiting to see how the fighting shook out and the two armies were forced to face one another alone, knowing weight that could tip the balance either way stood on the wings.

As the Tudor army marched towards the Yorkists, Richard ordered the cannons set off to deplete their numbers, while archers on both sides were deployed. Once Oxford’s men cleared the marsh, Norfolk ordered his own men to advance, the two contingents meeting on the base of Ambion Hill. When Oxford’s side began gaining ground, Richard ordered Northumberland to move and support him, but Northumberland’s side never did. Theories abound as to why, running the gamut of his men not being able to clear the marsh to outright betrayal. Either way, Norfolk was in bad shape.

In the midst of this, Richard caught sight of Henry at the rear and decided that the surest way to victory was to kill the prized pig. The gamble makes sense – in a one-on-one fight, the odds were with him. Richard and a smaller contingent of men charged the center, to which Henry responded by dismounting and hiding behind his men, his garb displaying nothing of his status so as to not call attention. The bodyguards surrounding him were able to slow Richard’s approach, and as this unfolded, William Stanley decided to make his move – for Henry.

The swarm of fresh men into the milieu pressed Richard and his party back. Legend has it that the King was offered a horse to ride away, but he responded, “God forbid that I retreat one step. I will either win the battle as a king, or die as one.” And so it was – within this final furor, Richard fought valiantly on foot, but was eventually struck in the head and killed, reportedly by one of Henry’s Welsh soldiers. As news of his death trickled through the remainder of his army, Northumberland and his man swiftly retreated north, while Norfolk was also killed in the fighting.

Northumberland was later arrested alongside Norfolk’s son, but was eventually released after pledging allegiance to Henry and even sent to represent the new King abroad. Four years later, he was killed by rioters in Yorkshire, with some calling for blood on the grounds of higher taxes and others citing his failure of Richard.

Say what you will about Richard, but even his critics note that he fought ferociously and died honorably. Later analysis of his skeleton in this century found that he was struck 11 times, some of them after he was clearly on the ground and separated from his helmet. Henry, on the other hand, not once attempted to prove his own bravery on the field, instead choosing self preservation above all else. Whatever the optics, it worked, for he lived.

Henry’s official historian would later tell the tale of Thomas Stanley crowning his stepson on site when he found Richard’s discarded crown in a hawthrone bush, but this is likely apocryphal. Bosworth, as it would later be known, would become a turning point, but its aftermath is a subject we’ll return to later. In the short-term, Oxford was restored to all the lands, estates and titles he had enjoyed during the reign of Henry VI, while Thomas Stanley was elevated to Earl of Derby and William Stanley made Henry’s chamberlain. As for poor George Stanley, he lived on. And thus the Tudor era began.