The Battle of Bosworth Field was incredibly unlikely.
People forget, now the the event is history and seems set in stone, how discombobulating everything must have been at the time, not least of all for Harri Tudur. You see, the man we think of as King Henry VII, founder of a dynasty and direct ancestor to Queen Elizabeth II, was never, EVER seriously thought of as a contender to the throne. The only reason the Yorkists wanted him done away with is because he might be used as a rallying point for rebels. As people got used to Edward IV’s reign, the idea that civil war would strike again waned in probability, and the need to capture Harri and his uncle Jasper Tudor was less and less urgent. Let the Welshmen stay in Brittney under house arrest by Duke Francis II; they were nicely out of the way there.
Then Edward died in 1483, and his brother declared Edward’s sons to be illegitimate and usurped their throne to become Richard III. Prior to naming the 12 year old King Edward V and his brother, 9 year old Richard of Shrewsbury, bastards, Richard did away with their most loyal and powerful supporters under unproven and flimsy charges of ‘treason’. Those men included Lord Hastings, who knew they were legitimate, their maternal uncle, Anthony Woodville, 2nd Earl Rivers, and their elder half-brother, Richard Grey. The arrest and murder of Woodville and Grey was carried out by Henry Stafford, 2nd Duke of Buckingham, one of Richard’s closest friends and seemingly unshakable ally. Edward IV’s sons were imprisoned in the Tower of London, and disappeared soon after.
Richard’s behavior upset a lot of people, both closet Lancastrians and die-hard Yorkists who were loyal to Edward IV alike. Before that, he had been popular because he was thought of as a loyal brother, and had repeatedly shown himself to be a just and fair administrator to Northern England. Taking the throne and imprisoning his nephews turned a goodly chunk of the populace against him.
The Edwardian loyalists, marshaled by the widowed Queen Elizabeth Woodville, organized a rescue attempt to free the Princes in the Tower in July of 1483, but it failed, perhaps because the Princes were no longer alive to be rescued. Moreover, there was a failed rebellion orchestrated by former confidant, the Duke of Buckingham, in October of 1483. Personally, I agree with historians like Maurice Keen who argue that rebellion against Richard III only began to think of replacing him with Henry Tudor when the Duke of Buckingham became involved because “Buckingham almost certainly knew that the princes in the Tower were dead.” There was obviously SOMETHING that had made the once devoted Buckingham turn against Richard, and the murdering of nephews is the most probable reason for such a drastic change of allegiance.
In short, only when there was no hope among the dissenters (who were increasing in number daily) of putting Edward V or Richard of Shrewsbury on the throne did those who wanted to unseat Richard III turn to Henry Tudor, a last ditch candidate with a very tenuous claim to the crown.
There is no way on earth that Henry Tudor would have won if he had gone up against Edward IV or Edward V. There would have been almost zero financial support or people willing to come to his banner. His own mother, Margaret Beaufort, would have dissuaded him, because it was hopeless. Also, she had become quite close to Queen Elizabeth Woodville, and thought more of Henry’s advancement as a peer than anything else. As Susan Abernathy explains:
In 1476, Margaret was in sufficient favor with the Yorkist court of King Edward that she attended Queen Elizabeth Woodville during the reburial ceremony of Edward’s father the Duke of York at the church in Fotheringhay. During the christening of Edward’s youngest child Bridget in 1482, Margaret was given the honor of holding the infant. Margaret eventually persuaded Edward to allow her son to return to England. In June of 1482, there was a draft pardon drawn up and discussion of Henry marrying Edward’s eldest daughter Elizabeth of York. [Other historians suggest that it was marriage to a younger daughter that was discussed, not Elizabeth.] But before all these arrangements could be finalized, King Edward died
Richard III initially tried to trust Margaret, because her powerful fourth husband, Thomas Stanley, appeared to be loyal to the new king. However, after Buckingham’s 1483 rebellion he found out just how much Margaret had colluded with the dissidents and she was placed under house arrest. Nevertheless, her husband, who had appeared to have remained loyal to Richard and was now Lord High Constable as well as the King of Mann, let her continue to have contact with her son.
Henry was safe at court in France with his uncle Jasper, and was busy trying to get financial backing for his invasion of England. Meanwhile, rebellious elements in England were clandestinely letting him know he was their man of the hour, when he was able to get his initial troops together. These kinds of negotiations, however, took time – as well as a lot of coded letters and backyard handshakes.
Time seemed be up after Anne Neville, Richard’s wife, died on 16 March 1485, because a rumor (almost certainly untrue) spread that Richard was going to marry Elizabeth of York himself. By this time, Richard’s once-high reputation was so in the toilet there were even rumors he had murdered Anne Neville just to marry his niece and consolidate his claim to the Yorkist throne. Although it is beyond contestation that the king didn’t murdered Anne Neville, he might have at least briefly considered wedding Elizabeth of York. It would have been one way to prevent her from marrying Henry Tudor, who had sworn an oath in Rennes Cathedral that previous Christmas to make Elizabeth his bride. Richard would have married her to someone else, but who to trust? Enemies of his reign were everywhere and marriage to Elizabeth could give a powerful nobleman a possible claim to the throne.
The rumor of a Richard/Elizabeth union galvanized Henry, and he made an appeal for urgency to Anne of Beaujue, and her husband, Peter II, Duke of Bourbon, who were acting as regents for the young King Charles VIII of France. Happily for the Tudors, Anne was very fond her cousins, Jasper and Henry. Anne therefore supplied them with the money, arms, and French troops for their 1485 attack on Yorkist England.
The Tudor invasion force sailed from France on 1 August 1485 with the English and Welsh exiles who were loyal to him and perhaps as many as 3000 French troops were were little better than mercenaries. On 7 August the Tudors landed at Mill Bay, a small secluded bay on the north side of Milford Haven. They easily capturing nearby Dale Castle, which put up almost no resistance to the incoming Tudor lords, in part because Jasper had been the rightful Earl of Pembrokshire for decades, and in part because Henry Tudor was:
hailed by contemporary Welsh bards such as Dafydd Ddu and Gruffydd ap Dafydd as the true prince and “the youth of Brittany defeating the Saxons” [who had come] to bring their country back to glory …they marched to Haverfordwest, the county town of Pembrokeshire, 12 miles away and were received “with the utmost goodwill of all”. Here, the Welshman Arnold Butler (who had met Henry in Brittany) announced that “the whole of Pembrokeshire was prepared to serve him”. Butler’s closest friend was Rhys ap Thomas [who also joined Henry’s cause] … Henry and his troops headed north towards Cardigan and pitched camp “at the fifth milestone towards Cardigan” where they were joined by Gruffydd Rede with a band of soldiers and John Morgan of Tredegar … Richard’s lieutenant in South Wales, Sir Walter Herbert, failed to move against Henry, and two of his officers, Richard Griffith and Evan Morgan, deserted to Henry with their men … After resting in Shrewsbury, his forces went eastwards and picked up Sir Gilbert Talbot and other English allies, including deserters from Richard’s forces.
Richard received the news of Henry’s arrival on 11 August and summoned his supporters. Still uncertain of the loyalties of Margaret Beaufort’s husband, Lord Stanley, the king took Stanley’s son, Lord Strange, as hostage to compel Stanley to fight on Richard’s side. Richard had also demanded Gruffydd ap Rhys ap Thomas, Rhys ap Thomas’s son, as surety, but Rhys ignored him. The Welsh have historically gone deaf when the English tried to boss them around, and Rhys was no exception.
On 22 August 1485, the two forces clashed at Bosworth Field in Leicestershire. The Tudor troops were profoundly outnumbered, and neither side was as yet sure what the Stanleys were going to do. Stanley hadn’t fully committed to his step-son, but when Richard commanded him to battle on the threat of executed Lord Strange, Stanley had told the king that, “he had other sons”. Richard’s other commanders talked him out of killing Strange on the spot, pointing out that Strange’s paternal uncle, William Stanley, was there to fight for Richard and that if he still wanted to kill Strange they could do it easier AFTER the battle. Their subsequent actions may indicated that they were secretly sympathetic to Stanley’s position.
Richard, who was an experienced commander and battle-hardened soldier, was in charge of his own troops. Henry, aware that he knew jack-shit about warfare, turned command over to John de Vere, 13th Earl of Oxford. A Lancastrian to his back teeth, Oxford had escaped his imprisonment in Hammes Castle, near Calais, to join Henry’s army.
It must be said that Richard fought valiantly, but regardless of his personal merit in battle he was doomed by the betrayal of some of his key allies. The Duke of Norfolk proved entirely loyal, but it cost him his life. When Richard saw that the men in Norfolk’s vangaurd were being defeated by an enemy formation now called the Oxford Wedge, the king signaled his reserve forces under Henry Percy, 4th Earl of Northumberland to enter the fray — but Northumberland did not. (This betrayal would later get Northumberland lynched in York, which remained true to Richard throughout.)
Naturally enraged by Northumberland’s immovability, it was then that Richard spied Henry Tudor under guard behind the melee. Richard decided the quickest way to kill the snake was to cut off it’s head. Gathering a few loyal men, King Richard III and his companions charged toward the upstart Welshman, determined to end the rebellion once and for all.
Richard came within a whisker of succeeding.
The king killed Henry’s standard-bearer Sir William Brandon as he attempted to get to Henry, and used his broken lance to conk former Yorkist John Cheyne over the head and knock him off his horse. Richard was now within a sword’s swing of ending the Tudors. The French mercenaries, being mercenaries, weren’t about to die to to defend Henry from the blood-soaked madman coming toward them, later excusing their actions by saying that they had been “caught off guard”. Henry, being no fool, didn’t try to fight Richard face to face, because he knew Richard would have turned him into chipped beef on toast. Instead, Henry “sought protection by dismounting and concealing himself among [the French mercenaries] to present less of a target.” Thankfully for Tudor historians, “Oxford had left a small reserve of pike-equipped men with Henry,” who held off the king and his men until Henry’s erstwhile bodyguards could muster some protector.
That’s when William Stanley turned his coat and revealed his true colors.
He led his men into the fight at Henry’s side. Outnumbered, Richard’s group was surrounded and gradually pressed back … near to the edge of a marsh. The king’s horse lost its footing and toppled into it. Richard gathered himself and rallied his dwindling followers, supposedly refusing to retreat … Polydore Vergil, Henry Tudor’s official historian, recorded that “King Richard, alone, was killed fighting manfully in the thickest press of his enemies” … The Burgundian chronicler Jean Molinet says that a Welshman [ struck the death-blow with a halberd while Richard’s horse was stuck in the marshy ground … The contemporary Welsh poet Guto’r Glyn implies the leading Welsh Lancastrian Rhys ap Thomas, or one of his men, killed the king, writing that he “killed the boar, shaved his head”. The identification in 2013 of King Richard’s body shows that the skeleton had 10 wounds, eight of them to the head, clearly inflicted in battle and suggesting he had lost his helmet. The skull showed that a blade had hacked away part of the rear of the skull.
With Richard III’s death, the Yorkists were no more.
Henry Tudor declared himself king “by right of conquest”, was crowned King Henry VII on 30 October 1485, and married Elizabeth of York on 18 January 1486. He was good king, often merciful to his enemies and was diligent about rewarding those loyal to him.
In honor of William Brandon’s death at Bosworth, Henry took Brandon’s toddler-aged son, Charles Brandon, into his own household, to be raised alongside the royal offspring. Brandon eventually became the 1st Duke of Suffolk and married Henry’s youngest surviving daughter, Mary Tudor, and one of their granddaughters, Lady Jane Grey, was briefly Queen of England. Charles Brandon would die 60 years to the day after his father, on 22 August 1545.