The unfinished business of Bosworth 1485

[Please note, this is an ongoing post that will be added to. It tells the tale of post Bosworth manoeuvres. How will this power struggle between Richard and Henry be concluded. If you like this sort of thing, please call back over the next few days and check on progress, which will be added in chronological order].

In the Year of our Lord 1485, in the Parish of Dadlington, Richard, our most noble king was sorely put to test by Henry Tudor, aided by the treachery of the Stanleys. With troubled days ahead, only loyal hearts can save all.

22nd August 1485

Bosworth battlefield lay strewn with the dead and the dying. The Lancastrians under Henry were victorious, but Richard III, the legitimate king was still alive. 

Towards the end of the battle, he had observed Sir. William Stanley send contingent after contingent of billmen over to Henry’s position and sensing that the odds were now heavily stacked against him, he heeded the advice of those around him and withdrew from the field with his body of horse.

Politically, he needed to be in London (south), but militarily, the moment called for him to move towards his northern strongholds. First he much catch up with Lord Percy (Northumberland), who just hours before had retired from the battlefield without becoming involved in the fighting - if nothing else, Northumberland’s force was at least fresh, offering some security if pursued.

There was of course the question amongst Richard’s party as whether Northumberland could be trusted, but Richard, ever pragmatic, knew that if he was to defeat Henry and the rebellion, then he must galvanise his northern support, not divide them. He was also somewhat accommodating to the fact that had Percy become involved in the fighting, his force would have been at least roughly handled and more likely destroyed, better to have Percy as a significant cadre to build another army around.

Choices for Henry were a little less clearcut. He was grateful for Sir. William Stanley’s intervention, but vexed that his support had only become so obvious, late in the battle. Of more immediate concern was why Lord Stanley had chosen not to show his support more demonstrably, but diplomatically he accepted the excuse that Stanley had been guarding the rebel flank from a possible manoeuvre by Northumberland.

Never-the-less, Henry was reluctant to send the Stanleys and their fresh cavalry in headlong pursuit of the fleeing Yorkists …. he wanted them on a tight leash for now! Not that the Stanleys had any hope of convincing Richard that they were still loyal to the crown - those bridges had been well and truly burned!

Instead, Henry sent off Sir. John Savage and his light cavalry to follow the retreating Yorkists and establish their movements and intentions

In due course, Henry would follow, taking the army to Nottingham, a Yorkist stronghold and a days march away. He believed Richard would retreat to that position and attacking him early, before he could recover his strength had obvious advantages. In any case, Nottingham, was a central location, if Richard had escaped him, from there Henry could strategically move either north or south as the situation dictated.

First, he needed to rest and re-supply his army. He sent heralds to the major population centres to give the news that Richard and the royal army had been defeated in battle and actively went about recruiting, hoping to persuade those who had hesitated in joining the rebellion, to do so now.

Time was not on Henry’s side, his war chest courtesy of the King of France (Charles VIII), still had the funds, for now, so he could continue to pay his French mercenaries and of course to others, he could make promises of titles once the crown was his!

1st September 1485

Ten days later, rested and re-organised, Henry had learned that rather than falling back on Nottingham (central England), Richard had moved North, with York being his likely destination.

Henry’s ranks were starting to fill with persons of note declaring their support. He was ready to start moving. 

The French and Scottish mercenaries under Philibert de Chandée would form the vanward, John de Vere 13th Earl of Oxford, reinforced by Edward Courtenay, Earl of Devon, took the mainward and the Stanleys were entrusted with the rearward.

In Henry’s most trusted circle was his uncle, Jasper Tudor, Earl of Pembroke. He would command a small reserve of 200 mounted men-at-arms. The total size of his force at this time was around 12,000 fighting men.

Henry voiced that this force, which would likely grow while marching, was strong enough to take control of London, from where he would have access to the Royal Treasury and operate the levers of power, such as denying Richard of tax revenue and in particular calling Parliament to consider Richard being declared a traitor.

Philibert de Chandée instead advised that Henry move north towards York and deal with Richard quickly by bringing him to battle (again). His caution lay in the question of how easy it would be to practically control London while King Richard was still at large. ‘We shouldst cutteth off the vip'rs headeth’.

Both Oxford and Jasper Tudor agreed with the French commander. However, the Stanley’s felt that the London option was the best, but Henry read their eagerness as the Stanleys reverting to a ‘hedging of bets’ stance, typified by them avoiding a commitment to conflict whenever possible and his mistrust immediately encouraged him to put his authority behind the decision to seek Richard out for battle. They would march north!

5th September 1485

Richard was both grateful to see the degree of potential support that remained loyal to him, but personally frustrated by virtue of his impatience at wanting to start the march south now, but he had heeded the warning of Viscount Lovell that the army was not yet ready.

The harvest was still being brought in and so the magnates had fewer men to spare than might otherwise have been the case.

Richard had lost most of his guns at Bosworth, but had managed to secure a small artillery train from northern nobles and local town arsenals, though a little time was needed for them to be assimilated into his army.

At a Council of War, it was agreed that the army should, if possible, avoid an engagement with the rebel army until such time that support from the south had joined the ranks of the royal army. With Henry likely to control the north/south road at Nottingham, they settled on Coventry as being the most practical rendezvous point for two weeks' time … 19th September. 

To make Coventry for that date, Richard’s army would need to start the 120-mile march in four days' time, on the 9th September, the 11th at the latest if the weather held. There was a renewed urgency in preparations.

Percy (Northumberland) would take the vanward, reinforced by additional bowmen from Viscount Lovell’s contingents. Richard would take the mainward and John de la Zouche  the rearward. Confidence amongst the royal army was slowly being restored. It was time to take the fight to Henry.

More to come ***************

Resource Section.

There is a post covering the Bosworth scenario on the blog, which describes the essential elements of the scenario and gives a brief AAR … which leads us to this journey. LINK;

https://battlefieldswarriors.blogspot.com/2026/07/bosworth-scenario-building.html

My sister webspace ‘COMMANDERS’  showcases the various figure and boardgame systems that I am enjoying and gives a flavour of where current projects are up to. Link;

https://commanders.simdif.com/dear_diary.html