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  • James Houser

August 22, 1485 - The Battle of Bosworth Field & Richard III

Updated: Jun 12, 2021

August 22, 1485. The place: Bosworth Field. The issue: who gets to sit in the big chair. The men: Henry Tudor, last scion of the House of Lancaster, on one side; the reigning King of England, Richard III of the House of York, on the other. It’s time to finally put an end to the thirty-year struggle for the throne that we now call The Wars of the Roses. And maybe talk a little about propaganda if we have the time.

It is finally, finally time to finish the story I left off on May 4 with the Battle of Tewkesbury. For anyone who needs a quick refresher: the English Wars of the Roses were a series of dynastic wars between the Houses of Lancaster and York between 1455 and 1487. After many terrible battles (including Towton 1461, the bloodiest days in English history including both world wars), intrigues, betrayals, and massacres, the wars seemed to have ended on May 4, 1471, when Edward IV of York and his brother, Richard Duke of Gloucester, destroyed the Lancaster army at Tewkesbury and basically wiped out the Lancaster clan. This included King Henry VI, Edward’s rival for the throne, who was taken prisoner and mysteriously (cough) died immediately following the battle.

After Tewkesbury, it looked like Edward IV’s rule over England was complete. There were no other family members of Henry VI knocking around with a direct claim to the throne; the closest relation left surviving was a young Welsh noble of all things. The 14-year-old Henry Tudor and his uncle Jasper fled England after Tewkesbury, and they were named traitors and had their lands confiscated by Edward as they took ship for France. Henry wound up in the hands of the Duke of Brittany, where he would be a captive for several years.

Henry Tudor’s claim to the throne was tenuous at best; he was a great-great-grandson of King Edward III through his mother. To sum it up, if you took a 23 and me and you have some English royal bloodline in you, you’re probably about as close to the throne as Henry Tudor was. Nevertheless, he was out there, and he was the closest thing anyone had to a tool to use against the Yorkists. The King of France gave Henry safe haven, but wasn’t about to go sponsoring any crazy adventures to “retake the throne” as long as Edward IV’s rule was firm. Edward didn’t even bother to try and hunt Henry down, regarding him as a “nobody,” and that was pretty justified.

In April 1483, twelve years after Tewkesbury, Edward IV died at the ripe old age of 40. This made his 12-year-old son, Edward V, the new King of England. Since 12 years old is barely old enough to run a lemonade stand, the actual rule of England fell to a Royal Council, which came to be increasingly dominated by the unpopular Woodville family.

Richard acted quickly – no one ever accused him of being indecisive. On April 29 he, along with his ally Henry Stafford, Duke of Buckingham, took young Edward V into custody along with several of the Woodvilles. Soon Richard was going chop-chop on the hated family, executing several members of their family for treason. But he didn’t stop there. On June 22, Richard convinced Parliament that due to a religious technicality, Edward’s and Elizabeth’s marriage had been illegal, so the young King Edward and his younger brother Richard were (gasp!) bastards. This obviously meant they could not inherit the throne, so the throne passed to – golly, would you look at that: Richard, Duke of Gloucester. So on June 26, the new top man in England was formally invested as Richard III.

The two young princes, Edward and Richard, were locked up in the Tower of London where they could be “kept safe,” of course. And they were never seen again. The fate of the “Princes in the Tower” is one of the most famous mysteries in English history, and there’s no question that within a couple of years they were dead – or were they? (?!?!?)

Of course, this not-so-subtle coup of King Richard’s didn’t win him a lot of friends from previous supporters of Edward and his family. This only got worse as 1483 turned into 1484 and people who wanted to see the princes in the tower were turned away. Soon Richard’s own ally Buckingham began plotting with young Henry Tudor, way off in France, to try and replace Richard. This ill-conceived plan fell apart pretty badly in late 1483, with Buckingham losing his head and Henry almost falling into a trap Richard had set for him. The problem was: despite his cynical coup, the uncertain fate of the princes, and Richard’s general nature, most of England was still lined up behind the sitting king.

I suppose now’s as good a time as any to talk about Richard III. Thanks to Tudor propaganda from later decades, most famously Shakespeare’s (excellent) play, Richard III has a reputation as a villain, in some ways the archetypal Villain. Don’t blame it all on Shakespeare; he mainly worked from histories and accounts of his age, which reflect the image of Richard that emerges from the play: a physically deformed, conniving, cruel and manipulative man who arranges the murder of many innocents to gain power. At the very end of the play, Richard is judged by the ghosts of his victims, who predict his defeat as payment for his many crimes.

Of course, Richard can’t be just responsible for the deaths of the princes, who, yeah, he probably murdered. In the play, he had to have also killed King Henry VI, and his own wife, and his brother George, Duke of Clarence. The play portrays Edward as a good king undone by the scheming of his brother, leaving aside that Edward HIMSELF had to have arranged the deaths of Henry and George, even if Richard committed them, since idk…he was the King? There’s a reason for the whitewashing of Edward, which I’ll get to.

The facts just do not bear out the story. Richard was not a limping, crippled, cackling hunchback (especially since a person with all those problems could not have gone out like a badass at Bosworth). He was robust and slender, a valiant battlefield commander who played rough sports and fought well. Despite later being the “uber-villain,” Richard III was no Hitler of his times. He was a very, very typical ruler of the Late Middle Ages: amoral, scheming, somewhat cruel and intolerant of treason. In the modern day, yes, Richard would be a bad dude without question. In the Late Middle Ages? There was nothing Richard didn’t do that everyone else at the time hadn’t done or wouldn’t do to gain and maintain power. He probably wasn’t even the worst person in the Wars of the Roses – that seems to pretty universally go to Queen Margaret, Henry VI’s wife. The one crime we can really ascribe to Richard (the deaths of the Princes in the Tower) is NOT a settled question, as we will soon see.

Henry Tudor saw his chance to take the throne of England in 1485, after Richard got caught up in the London rumor mill and saw his approval ratings tank. The rumor was that Richard had murdered his late wife Anne Neville and was scheming to marry his own niece Elizabeth, daughter of Edward IV, to cement his claim to the throne. The rumor was prominent enough that Richard had to make a public proclamation that it was untrue, which any PR guy could tell you is only going to make people talk more. This rumor is treated as fact in Shakespeare, even though there is NO evidence for it. Henry himself was trying to marry Elizabeth to cement his own claim to the throne, so he stoked the rumor and used it as an excuse to invade.

Henry crossed the English Channel in the summer of 1485 and landed in Wales with almost 5,000 French and Scots mercenaries put at his disposal by the French King. Marching across Wales, he at first met a muted response, but soon gathered a large number of supporters who saw his Welsh descent as a boon. By August 15, Henry had crossed the English border and was making for London. Soon disaffected English lords were also joining his cause, hoping to overthrow Richard.

Richard was no slouch: he had been well aware that Henry Tudor would make a second attempt, and as soon as he got word of Henry’s landing he was putting together an army. Part of this army would be led by Lord Stanley, a well-known bellwether who always managed to end up on the winning side. Stanley and Richard were on uneasy terms, especially since Stanley was married to Lady Margaret – Henry’s mother – which made his loyalty doubtful. When Stanley had not joined Buckingham’s revolt in 1483, however, Richard put him in the “trustworthy” column, a move he would soon regret. The truth was that Stanley had been in correspondence with Henry since he landed, and was basically just waiting for his moment to choose sides. Just to hedge his bets, though, Richard took Stanley’s oldest son hostage before the battle began.

Richard took his position on Ambion Hill, south of the small town of Market Bosworth. By August 21, Henry’s army had come to confront him, and both sides prepared to fight on the morning of August 22. Numbers for these medieval battles are always fudgy, but all sources agree that Richard had significantly more men than Henry. He deployed to the north, with spearmen guarding his archers and cannons (yes, we’re at the point where people are using cannons on the battlefield) and his heavy cavalry ready to charge. To the south, on the other side of a marsh, Stanley’s troops had come up. Together the two forces would be in a position to envelop and destroy Henry’s army – but this would only work if Stanley attacked.

Henry began the attack on the morning of August 22, 1485. With almost no military experience to speak of, he allowed his generals to direct the battle, and his army marched up the hill in a solid mass to try and break through Richard’s center. Richard’s longbowmen and the archers tore great gaps in the French mercenaries and Welsh tribesmen as they pushed forward in a close phalanx. Thanks to their dense formation, though, they were able to achieve local superiority on Richard’s right flank and began to push it back. Due to some miscommunications, Richard’s left line did not engage Henry’s army, so that Henry actually had slightly more troops in the battle.

Both sides sent messengers to Stanley, who had several thousand men standing off to the side of the battle, ready to intervene when he figured out which side he was on. Richard sent a fearsome message threatening to execute Stanley’s son if he did not attack, to which Stanley only replied “I have other sons.” Henry also asked for Stanley’s support, but Stanley’s reply was evasive. So an uncommitted force sat watching the battle, waiting to see which way the wind blew.

At some point, Richard spotted Henry, hanging back from the main force with a small detachment of cavalry. Richard decided to end the fight quickly by killing the enemy commander and putting an end to this Lancaster-York crap for good. He took a detachment of cavalry, swung wide around the infantry melee, and made a headlong charge at Henry.

This is a good time to note that a severely crippled, cackling hunchback could not have done any of this.

Richard plowed into Henry’s bodyguard like a typhoon. He killed the Tudor claimant’s standard-bearer with his lance in the initial charge, and began to tear into the rest of the knights, killing the great tournament champion John Cheyne with his own broken lance. Henry, panicked, dismounted and tried to hide from the whirlwind unleashed by Richard III. Shakespeare has the two men meeting in battle and Henry slaying Richard. This is obvious fantasy; Richard was the veteran of years of campaigns and dozens of battles, while Henry…wasn’t. It would have been like handing a Chihuahua to a Mastiff. Richard came within a sword’s length of Henry Tudor, almost changing English history forever, before the winds shifted.

And THAT is when Stanley made his move. The Stanley forces came riding to the aid of Henry, surprising Richard and pushing his force back into the swamp. (Threaten to kill my son, will you?) Richard’s horse toppled at the edge of the marsh, and the King was left unhorsed and in the soft ground of the marsh as the Stanley men closed in. Despite Shakespeare’s claim that he shouted for a horse, Richard refused to retreat: "God forbid that I retreat one step. I will either win the battle as a king, or die as one." It was there that Richard was finally surrounded by infantry and, despite killing several, was cut down with a halberd-blow to the head.

In 2012, Richard’s skeletal remains were unexpectedly found beneath the ruins of an old church in Leicester, England, and later reinterred in the local cathedral. DNA testing matched with his known descendants and confirmed the King’s identity. Analysis of his remains showed 11 wounds, nine to the head, suggesting he lost his helmet in the melee. All we know is that, whatever his personal faults, Richard went out like a baller.

With Richard’s death, his army fled, and Henry was victorious in the Battle of Bosworth Field. Richard’s crown was plucked from a hawthorn bush and given to Henry, who claimed it by right of conquest. Henry became King Henry VII, beginning the celebrated Tudor Dynasty, and almost immediately the process of myth-making began.

Henry, of course, wed Elizabeth of York, the daughter of Edward IV and niece of Richard. This marriage was supposed to unify the White Rose of York and the Red Rose of Lancaster – hence, the red-and-white Tudor rose to symbolize the merging of the two dynasties and the coming of peace. This meant, of course, that some history would have to be rewritten. It meant that Elizabeth’s father, Edward, would have to be recast as a noble king and good man – otherwise, her ancestry would be attainted. It also meant that Henry’s claim to “right of conquest” had to be couched in moral terms, since his bloodline was so distant from the English royal family.

The obvious solution was to pin the blame for every bad thing since who knows when on Richard III. This included ascribing all Edward’s worst deeds to him and “verifying” every bad rumor ever whispered about him, so that it wasn’t just an ambitious power play but a MORAL victory when Henry defeated Richard. Richard III was the scapegoat for all the Kingdom’s ills – the historical sacrifice for the Tudor peace. (It may have also been Henry’s way of concealing the fact that he had hidden behind his bodyguards when Richard was bulldozing right through them.)

And would you believe that wasn’t the end of the Wars of the Roses? In 1487, a fresh rebellion began, fronted by a young man who CLAIMED to Richard of York – the murdered Prince in the Tower. Henry VII’s defeat of this rebellion at Stoke – an even larger battle than Bosworth – is considered to be the true end of the Wars of the Roses. Even after that, another claimant named Perkin Warbeck ALSO claimed to be Richard of York throughout the 1490s. The mysterious fate of the princes sponsored many conspiracy theories for the rest of Henry VII’s reign – not least, that Richard III had left the princes alive but Henry murdered them when he found them after Bosworth.

So the final piece of Tudor propaganda falls into place. To this date, most people have no doubt that Richard III murdered the Princes in the Tower – but any and all evidence to the contrary may have been suppressed and destroyed by Henry VII to erase all doubt. If Richard III murdered the Princes, then they could hardly be popping up to challenge Henry’s rule, could they? Still, one wonders…and no one knows for sure what happened to the Princes in the Tower to this very day.

History gets muddier the deeper you look.

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