Alternate history: what if Richard III had won at Bosworth?

“With the larger army, substantial ordnance and archery, and a fighting ground of his choosing, Richard was best-placed for a defensive battle,” says Michael Hicks, Professor Emeritus at the University of Winchester and author of Richard III: The Self-Made King (Yale, 2019).

“Henry had to attack a strongly entrenched position.” Yet Richard famously lost the day, ending 331 years of Plantagenet rule and ushering in the Tudor dynasty, as key allies failed to join the fray and, in some cases, actually turned on their king and attacked his flank.

Henry gambled everything on achieving a decisive victory with his 5,000-strong army, an uneasy alliance of Lancastrians, disgruntled Yorkists, Bretons, French, Scots and Welsh

If the brothers Lord Thomas and Sir William Stanley had stayed loyal to Richard – or if they had heeded the king’s warning that he would execute Thomas’s son if they didn’t fight for him– and if Henry Percy, Earl of Northumberland, had come to Richard’s aid, then Henry Tudor’s reign might never have begun.

Henry gambled everything on achieving a decisive victory with his 5,000-strong army, an uneasy alliance of Lancastrians, disgruntled Yorkists, Bretons, French, Scots and Welsh. The pivotal moment came when Richard, spotting Henry at the rear of the action, led a mounted charge. Breaking through, he unhorsed the mighty John Cheyney, killed Henry’s standard bearer and came within killing distance of Henry himself. With one more slash of his blade, Richard could have ended Henry’s bid for the throne and made safe his own rule. Hicks says: “Richard would have continued to reign with his dynasty secured. It’s unlikely another formidable threat could have been raised for years, if then.”

Would the Tudors have become a historical footnote?

Henry may well have perished in the battle, along with his uncle Jasper, leaving no heir to carry on his claim. “If Henry had died, who knows who might have taken his place as contender to the throne” says Hicks. “His strength was that he was not Richard. But how could a newcomer secure support?” Even if, in the case of a Yorkist victory, Henry had survived, what awaited him would have been capture and possible execution or exile. The name of the Tudors would have become nothing more than a historical footnote.

With victory in battle seen as proof of God’s favour, Richard – even though he had faced stern opposition following his taking of the throne in 1483 and the disappearance of the Princes in the Tower – could have strengthened his position

With victory in battle seen as proof of God’s favour, Richard – even though he had faced stern opposition following his taking of the throne in 1483 and the disappearance of the Princes in the Tower – could have strengthened his position. In the aftermath, he would undoubtedly have extinguished any remaining Lancastrian support and taken vengeance on those who had not supported him. “Richard had a track record for executing opponents and would certainly have disposed of the Tudors, the Earl of Oxford and any traitors,” says Hicks. This may well have included the Stanleys and Northumberland.

A priority of Richard’s continued reign, with significant political, diplomatic and dynastic implications, would have been to remarry. He had lost his son and wife Anne within a year so securing a new queen would have been vital. “Richard needed a fertile wife able to bear children,” says Hicks. “She would need to have been a lady of royal or perhaps noble birth, but definitely not a parvenu and widow, which his brother Edward IV’s queen, Elizabeth Woodville, had been.” A promising prospect was Portuguese princess Joanna, sister of John II, as this union would have formed a strategic alliance.

Richard may have looked to enhance this alliance by marrying his niece, Elizabeth of York, to John’s cousin, Manuel. Hicks suggests that Elizabeth may even have been Richard’s option for his own bride. “Marrying Elizabeth would have strengthened his own position and denied her title to foes. Richard would have needed to seek approval from the Pope for the union, but there were precedents to uncle-niece marriages.”

Richard could then have turned his attention to governing the realm. Pursuing a commitment to law and justice, and a willingness to reform, as seen in the years before Bosworth, he may have made further changes to the legal system, which could have benefited the poor and under-represented. His sights would also have been on foreign matters. Although the French had aided Henry, Hicks points out that they were never “officially hostile and so would have cultivated good relations”.

By fostering relations with France, Spain and Portugal through marriage alliances or treaties, Richard’s ongoing reign would still have impacted England in the decades after his death. If there was no Tudor dynasty, there would have been no Henry VIII. So, as Reformation swept over Europe, England may have remained Catholic – Richard was a pious and conventional Catholic, and his successors would probably have been the same – or, at least, not moved over to Protestantism as quickly as seen in the 1530s with Henry VIII’s split from Rome.

“If Richard continued after Bosworth, he would have been a more consistent ruler than Edward IV, similar to what we saw in Henry VII’s centralising and authoritarian rule, and more conventionally chivalric,” says Hicks. Now regarded as a divisive figure – murderer or misunderstood? – Hicks concludes that Richard could instead have been seen as a “competent medieval king, seldom remembered”.

Michael Hicks is Professor Emeritus at the University of Winchester and author of Richard III: The Self-Made King (Yale, 2019). He was speaking to freelance writer Jonny Wilkes

This article was first published in the November 2020 edition of History Revealed