Last summer I posted about how I intended to write a series of short essays posing theoretical “what ifs” about elements of Tudor history. The ideas included: what if Prince Arthur lived and Henry VIII never became king, or what if Mary I was able to convert England back to Catholicism, or what if the Spanish Armada won in 1588 against Elizabeth I. I was quite excited about these various scenarios, however, come September I was no longer teaching the Tudors module at A-level and so things went quiet for a while.

But on walking home earlier today I considered this potential series once more and thought I would attempt the first one of the list: what if Richard III won at the Battle of Bosworth in 1485, rather than Henry Tudor. And what a better place to start, for Bosworth was the true birth-place of the Tudor dynasty; the Plantagenets were ended and a new family was put in their place.

Historian Chris Skidmore outlines the defining moments of the battle in 1485:

‘Spotting Henry at the back of the battlefield, surrounded only by a small band of soldiers, Richard charged on horseback towards it ranks. After unhorsing Sir John Cheny, at 6ft 8ins one of the tallest soldiers of the day, Richard’s men managed to kill Henry’s standard-bearer, Sir William Brandon, while Richard’s own standard-bearer, Sir Percival Thirlwall, had both his legs hacked away beneath him.
With Henry fearing imminent death, the sudden charge of Sir William Stanley’s 3,000 men saw Richard swept into a nearby marsh, where he was killed as the blows of the halberds of Henry’s Welsh troops rained down on him. Thanks to Richard’s remains having recently – and finally – been discovered under a Leicester car park, we know that the king suffered massive trauma to the head, including one wound which cut clean through the skull and into his brain. With the king dead, after two bloody hours the battle was won over: on the nearby “Crown Hill”, Henry was proclaimed king…’

However, what if the battle turned out differently? What if Richard’s fatal charge actually succeeded and he managed to strike at and kill Henry Tudor? I present here five possible outcomes from a Richard III victory at Bosworth.

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1. Tudors in the Rubbish Bin of History

If it was not victory then only two realistic options would have laid out to Henry after defeat at Bosworth: death or retreat. Even if he had survived it is unlikely that Henry would have mustered up any further threat. His invasion in 1485 was a gamble in which he headed an uneasy coalition of vengeful Lancastrians, disgruntled Yorkists, manipulative Woodvilles, and men in the pay in the French king. Like most other failed invasions of the kingdom throughout history the failure would have been sign enough from God that it was Richard who was favoured.

With Henry’s alliance crumbling to pieces he would have been forced to flee back to Wales, but yet remaining in the British Isles would have saw his eventual capture and execution at the hands of Richard. Furthermore, on the continent he would have lacked allies: Duke Francis of Brittany would have been wise to steer clear any link, whilst the French king would not have been pleased that his contribution was so easily squandered. Perhaps the only available option to Henry (and Uncle Jasper, if he also survived), would have been exile to the far-flung corners of the known world.

However, escape from the battle-field would have been unlikely. If Richard’s charge into the fray had succeeded then Henry would have been cut to pieces, with Richard needing to show off the corpse to claim a complete and utter victory. But his wrath would not have ended there. After all, Richard had witnessed and participated in the destruction of the Lancastrians in 1471, back when Henry VI and his son were killed to ensure that there were no others who held designs on the throne.

In which case, Richard would have sought out all remaining Tudors to utterly destroy. This itself would not have been too tough a task, for only a handful remained. With Henry and Jasper killed on the battlefield, it would have been the turn of Margaret Beaufort to face execution. Her marriage to Lord Stanley had protected her before Bosworth, but if Stanley had pulled the dirty on Richard this would have spelt the end of her (and the Stanleys). Even if the Stanleys had withheld their support for the Tudors at Bosworth it is more than likely that Richard would have waited for a moment to strike to unleash his fury.

All of this would have meant that the Tudors would have been utterly annihilated from history. In which case, they would have gone down as nothing more than a mere footnote. As Trotsky famously once said, the Tudors would be consigned to the rubbish bin of history.

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2. The Two Hundred Years’ War?

With the Tudors removed from the scene and with stability restored in England, Richard would have set out ticking off those on his revenge list. As noted above, the remaining Tudors – chiefly Margaret Beaufort – would have been imprisoned (and possibly killed). Beyond this there remained many others that Richard needed to met out a harsh revenge.

The Stanleys are the biggest “influencers”: if they had helped Richard at Bosworth it would have led to greater rewards and titles. If this was the case, Richard would have had to tread carefully in terms of how he dealt with the brothers: the rise of their profile mirrored, in many ways, that of the Kingmaker from the Wars of the Roses. However, a dismantling of the Stanley power-bloc could have been a long-term plan, and with decades left to rule he would have had time to achieve it.

However, if the Stanleys assisted Henry at Bosworth (as happened in real life), Richard would have needed to deal with them swiftly. Even both brothers survived the battlefield, Richard could have utilised acts of attainder from Parliament to severely punish them: removing their titles and land. Bereft of everything the only thing left to the Stanleys would have been humiliating and lonely exile.

And what of the others who fought against Richard at Bosworth? He would have looked on Wales with greater suspicion, considering the number of nobles and men who backed Henry on his march through the region. Perhaps he would have taken an army into Wales to raze a few towns to show his anger and to re-establish his authority. Furthermore, he would have more than a few harsh words with the Earl of Northumberland; an ally who seemingly refused to fight at Bosworth. Removing Northumberland from the post of chief noble in the North would have been a priority.

Richard’s revenge would have extended further from the British Isles. The King of France backed Henry Tudor’s attempted invasion with ships, men, and money. Such an act was virtually a declaration of war, and having re-established his position at home, the next step in Richard’s plan would have been the gathering of an army to take the fight to France. At this juncture, perhaps he would have played the strategy in the same coy scheming manner as his older brother Edward IV in the 1470s and as Henry VII did in the 1490s: invade with no real intention of fighting but rather with the aim of obtaining a better deal.

I like to think that Richard would not have been sated with a new peace treaty and a pension: for him, removing the French king would have been uttermost in his mind. In which case, the Hundred Years’ War would have been renewed once again, because even with a more stable base Richard would have been up against a much stronger power. The struggle could have been extended with a new generation, thereby leaving historians with the possible idea of naming it the Two Hundred Years’ War.

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3. England Remains a Catholic Nation

Richard’s short reign of two years was filled with suspicion and paranoia, thereby not giving us concrete plans of how he would have reformed England. However, there are a couple of examples which provide an indication. It appears that Richard would have centralised power to London, taking it away from the regions. This itself was a key development of the Tudor dynasty, marking a shift from the medieval world and problems of the power of the nobility during the Wars of the Roses; in which case, Richard could have trumped the Tudors.

Interestingly, Richard could have gone down in history as a man who promoted culture, rather than as a man of war. In 1484 he founded the College of Arms, and also removed restrictions on the printing of books. He also set out to reform the law system, adding an additional layer of professionalism. Such reforms in such a short space of time leaves us wondering what more could have come.

However, perhaps the most significant change would have been the religious make-up of England. Without the self-interested decisions of Henry VIII there would have no English reformation; after all, Henry chiefly wanted a divorce to enable him to marry another, and the doctrinal debate of the positives and negatives of Protestantism and Catholicism held little interest for me.

Is it as simple to reduce a great transformation of English history to “No Henry = No Reformation”? No, of course not. However, it is true that without Henry VIII a major catalyst of change would have been removed. Perhaps a reformation may have occurred later in the century, but it is unlikely to have had the same force or even same chance of success as the Henrician Reformation of the 1530s.

And what of the later ramifications? England would have been more closely knit to the on-goings with the principal Catholic states of Europe, principally France and Spain. This may have forestalled or entirely killed off prospects of English exploration and colonial expansion in the Americas and elsewhere in the world. Furthermore, even if there were to be English colonies in North America those colonies would have been chiefly Catholic.

4. The Doomed Yorkists?

Even with victory at Bosworth there is little likehood that Richard’s own progeny and Yorkist dynasty continues after him. Although he was only 32 at the time of his death, Richard’s short reign was marked tragedy in which both his wife and heir died. Such deaths have been used to cast aspersions against Richard’s reign, as if he was cursed due to his bloody coup in 1483. However, if he survived Bosworth there was every chance that he would marry and sire more sons and daughters.

The poor match that was touted during this period was Richard’s very own niece: Elizabeth of York. Elizabeth was the daughter of Richard’s brother, Edward IV, and had claimed the attention of Henry Tudor. In reality, Henry married Elizabeth in early 1486 and together they had four surviving children (one of which became Henry VIII). As early as 1484 Richard was aware of Henry’s designs on Elizabeth and therefore he considered marrying her in order to trump his rival.

Despite the gruesome-ness of the incestuous match, it is possible that this union would have brought about heirs. But there are some who believe that this was not entirely probable due to Richard himself, with A.L. Rowse once suggesting that Richard ‘had no interest in sex.’ If this is to believed then perhaps Richard never fancied his kingly duties in the matrimonial bed; in which case, Richard could have ruled for several more decades but yet would have had no son on which to pass his crown.

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5. The De la Poles become England’s favourite dynasty

With Richard unable to provide male sons the crown would pass from the Yorkists to a new family name: the De la Poles. This family has been largely forgotten from this era of history, but yet it is possible that they could have taken the place of the Tudors in our attentions and affections.

The link to Richard is through his sister Elizabeth, who married the Earl of Suffolk, John de la Pole. They had many children together, including some notable sons: John, Edmund, and Richard. Each of these three provided problems for the Tudors, with John the probable brains behind the Lambert Simnel Rebellion in 1487 (when he was killed), Edmund escaping to the continent in the early 1500s before being returned (and later killed by Henry VIII), and Richard plotting in Europe being succumbing during the Battle of Pavia in 1525.

On the death of Richard’s wife and only heir in 1484 he changed his heir apparent to his nephew, Elizabeth’s oldest son, John de la Pole. This meant that if Richard failed to have any children the crown would have passed into the De la Pole name. And with plenty of sons, it is clear that the crown would have remained in their hands for generations to come.

The Tudors have become established as England’s most loved dynasty, but I think there is scope that honour to have been bestowed on the De la Poles. After all, they were a scheming and conniving lot, with plenty of drama to provide entertainment for future history buffs. In many ways it is a shame that their exploits were short-lived and they were confined to live their lives in the shadows after the fall of Richard at Bosworth in 1485.