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Henry Tudor’s Invasion

The shortest route for Henry Tudor’s invasion fleet would have been to land off the southeast coast of England near Kent, which is exactly what Richard expected. Instead, Henry took a much longer route, sailing west through the English channel around the southeast tip of England, then turning north for Wales. Even though he had 4,000 men in his army, it wasn’t nearly enough to face the royal army.¹ His only chance was to pick up more men, mostly Welshmen, for his army. He was counting on Jasper’s popularity and his own Welsh roots to reinforce his troops.

Just before sunset on 7 August 1485, Henry Tudor’s troops came ashore on the Pembrokeshire peninsula of Wales near the village of Milford Haven. When Henry’s feet touched Welsh soil for the first time in fourteen years, he fell to the ground, kissed the sand, and said aloud ‘Judge me, O Lord, and plead my cause.’² Then Henry rallied his men and set off on their march through Wales in the name of the lord and Saint George, the patron saint of England.

The first mission of the Tudor army was to get control of Dale Castle, twenty-four kilometres to the west, which Henry believed was being held in Richard’s name. Henry was pleasantly surprised when the inhabitants handed over the castle to him without a fight. His army spent their first night in Wales at Dale Castle, then headed out early the next morning for the town of Haverfordwest, twenty kilometres to the northeast.³

For the next two weeks, Henry and his rebel army trudged north through Wales, hugging the coastline to the west and the Cambrian Mountains to the east. Following the west Wales coastline certainly wasn’t the most direct route to get to Richard at Nottingham or to even make a run on London. But Wales was a dangerous place for many reasons. Richard had strong support in southeast Wales so Henry had to avoid that region entirely. Instead, he plotted his march so that it would pass through north Wales where Sir William Stanley held land and northwest England where Lord Stanley held all the power. Henry needed the Stanleys desperately. Without them and their huge armies, Henry would have been doomed. Henry wrote to his mother and both Stanley brothers on 2 August from Aberystwyth in which he told them the route he had decided on to infiltrate England.⁴

On 4 August, Henry Tudor and his rebel army reached Machynlleth, a small town that held special importance for the Welsh people as it was there in 1404 that Owain Glyndŵr was crowned as Prince of Wales.⁵ Machynlleth called itself the ‘ancient capital of Wales’ and the significance was not lost on Henry Tudor. The Welsh were a superstitious people who yearned for freedom to rule themselves instead of their English overlords. For hundreds of years, Welsh prophets foretold the coming of ‘Y Mab Darogan’, a Welshman who would free Wales from English oppression.⁶ Over the previous millennium, many Welshmen had been prophesied as Y Mab Darogan, including Owain Glyndŵr, but they were still waiting for the one to arrive. In Henry Tudor they saw an English noble with Welsh blood, a man bold enough to challenge the sitting king of England. The Welsh had hope that at last the mab darogan had arrived and they threw their support behind him. Henry was hugely relieved when Rhys ap Thomas agreed to join him, bringing about 2,000 men to Henry’s army.⁷

In the past seven days, Henry and his army had travelled around 150 kilometres north through Wales and now as they faced the Snowdon mountain range at Machynlleth, they turned due east and began their approach to England. It took Henry’s army a three-day march over rough terrain to travel the eighty kilometres from Machynlleth to Shrewsbury which he expected to be friendly to his cause. However, when Henry and his army arrived at Shrewsbury on 17 August 1485, the portcullis was brought down and they were denied entry to the city. This was the first resistance Henry had encountered in the ten days he had been back on the island of Britain. It was only when Sir William Stanley sent the town bailiff an urgent message to admit Henry Tudor that the portcullis was opened and Henry’s troops were allowed to pass through the city.⁸ Later that day, Sir William Stanley himself arrived in Shrewsbury to treat with Henry. This was their first ever face-to-face meeting and no doubt they measured each other up.⁹

After leaving Shrewsbury, the rebel army continued east into England, gathering more and more supporters with every passing day. To add to the numbers of Welshmen he had picked up on the first part of his march, now Henry was picking up discontented Englishmen who either had connections to the Stanley family or else remained loyal to Edward IV. At Stafford on 19 August, Henry received a further 1,300 armed men for his army courtesy of Sir Gilbert Talbot, son of the earl of Shrewsbury, and Sir Richard Corbet.¹⁰

20 August 1485 was a momentous day in the lead up to the Battle of Bosworth. On this day, Henry and his enlarged army entered the city Lichfield and was openly received by its people which was a very encouraging sign. Soon after arriving, Henry was visited for a second time by Sir William Stanley so they could seal their final plans. William informed Henry that Richard was only one to two days’ march away at Nottingham and Henry should get going soon before Richard blocked his path to London. Henry heeded Sir William’s advice. That day he mobilised his troops and had them marching past nightfall. Henry and his closest advisers were riding at the very back of the army so they could discreetly discuss their plans. At some point Henry’s and his entourage became separated from the main Tudor host and spent a frightening night lost in the countryside. It wasn’t until the next morning that Henry found his army camped near Tamworth and rejoined the host.¹¹

Henry wasn’t the only one who had a busy day on 20 August for that is the day Richard finally chose to react to Henry Tudor’s invasion. At first it seems Richard didn’t take the threat of Henry Tudor very seriously. It was on 11 August that Richard learned of Henry’s landing, yet he didn’t activate his army until 20 August.¹² Why did he delay? His scouts had reported Henry’s army to be rather modest and perhaps Richard believed that his Welsh allies and the Stanleys would put down Henry and his rebels, which was quite naïve. Richard severely underestimated Henry’s ability to gain Welsh supporters and he overestimated the loyalty of his own men, specifically the Stanleys. It wasn’t until 19 August that the true picture of deceit was painted by Lord Strange’s confession.¹³ Lord Strange was the son of Lord Stanley and was being held ransom by Richard for his father’s good behaviour. Lord Strange attempted to escape from Richard at Nottingham but was captured. Upon interrogation, Lord Strange confessed that his uncle Sir William Stanley was working in concert with Henry Tudor but insisted that his father, Lord Stanley, husband of Margaret Beaufort, was entirely loyal to Richard. Richard naively believed him.

After the shock of Lord Strange’s confession on 19 August and the news that Henry Tudor had passed through Shrewsbury untouched, Richard finally decided to take the threat seriously. His supposed allies had not stopped Henry’s progress as he had planned, and now the loyalty of all his allies were in doubt. Richard decided to take matters into his own hands. His scouts reported Henry’s location in Lichfield and that Henry was on the road east towards London. Richard scrambled together his army at Nottingham and rode forty kilometres south to Leicester, east of Lichfield, to block Henry’s path.

On 21 August 1485, the day before the most important battle of their lives, Henry and Richard were busily preparing their men for the showdown. At Leicester, Richard donned his crown and led his troops in procession to Atherstone with great fanfare. He selected a high ridge in proximity of Ambion Hill for his army to camp for the night.¹⁴ Meanwhile, Henry had one final meeting with the Stanleys to firm up their battle plans. To Henry’s great disappointment, the Stanleys insisted on keeping their private armies separate from Henry’s main army. Instead, Lord Stanley sent Henry four of his best knights to join Henry’s host.¹⁵ This was hardly the support Henry expected but if Lord Stanley was to help Henry, he would have to make Richard think he was loyal up until the very last moment. With time running out, Henry ordered his army to camp that night near Atherstone, just a few kilometres west of Richard’s camp.

Early on 22 August 1485, King Richard awoke in a foul mood. He reported to his men that he had been disturbed all night with terrible dreams and had not had much sleep. When he tried to get breakfast, his camp was so unorganised that he could not find a cook, nor could he find a chaplain which vexed him greatly.¹⁶ Richard still had the advantage though. Estimates put his army at nearly double that of Henry Tudor’s which numbered around 5,000.¹⁷ However, Henry did have some very experienced military leaders on his side, including his uncle Jasper Tudor, John de Vere, Earl of Oxford, Sir Edward Woodville, and Margaret Beaufort’s half-brother, Lord Welles. When it was time for the battle to commence, Henry Tudor rode up and down the front line of his army, firing them up for the bloody clash that was about to unfold. Richard likewise gave his troops a similar pep talk, all while wearing his treasured crown of England.

The Battle of Bosworth is very poorly documented, but historians do agree on at least a few aspects. As the two armies lined up across from each other on the battlefield, the action most likely commenced with a brief round of archers and cannons. Then the two vanguards of Henry’s and Richard’s armies simultaneously moved towards each other. Richard had the better position high on the ridge. Henry’s vanguard, led by the earl of Oxford, found itself in a poor position near a marshy area at the bottom of Ambion hill. Oxford quickly swung his line around the bog and met with Richard’s army with violent hand-to-hand combat using axes, sword, and pikes.

While the melee was going on, Richard’s scouts came to him and reported Henry Tudor’s location. It turns out Henry was largely unprotected on the battlefield, only surrounded by a small group of bodyguards. Richard saw this as a golden opportunity to take Henry out. Richard gathered some of his horsemen and charged towards Henry’s small group, smashing into them with full force. Richard mercilessly hacked his way through the outer circle of Henry’s bodyguards, killing many in his path, including Henry’s standard bearer, Sir William Brandon.¹⁸ As he neared closer to Henry, it looked like all hope was lost for the would-be Tudor king. Unless someone came to his rescue, it would only be a matter of minutes before Richard would reach him and cut him down.

That’s precisely when the Stanleys decided it was time to join the battle. While Henry and Richard had lined up their men before the battle, the Stanleys stationed their armies about a kilometre away from the battlefield, just near enough to watch the action unfold. It was only when they saw Richard about to overtake Henry that they committed to the battle. Sir William Stanley’s army of 3,000 soldiers swooped down onto the battlefield where Richard and Henry were about the come to blows.¹⁹ Richard and his worn-out men were no match for Stanley’s fresh soldiers. When they rushed the battlefield, Richard’s army scattered in confusion and fear as the Stanleys were supposed to be fighting for the king, not against him. Despite the odds suddenly turning against him, Richard fought on bravely, even refusing a horse to flee to battlefield. He was determined to put an end to Henry Tudor or die trying. And die he did. Richard was quickly overwhelmed by the surge of Stanley’s soldiers. Around this time his battle helmet came off, either accidentally or on purpose, and he was killed by several blows to the head.²⁰

With Richard now dead, the remainder of his soldiers fled the battlefield and the Tudors proclaimed themselves victorious. The old story goes that Richard’s crown was found under a hawthorn bush and brought to Lord Stanley who ceremoniously placed it atop Henry’s head. Henry then thanked god and his men for their victory to which they replied ‘God save King Henry!’ Henry ordered that the wounded be tended to and the dead buried.²¹

The following day, Henry and his victorious party made their way to Leicester where Henry was received as the new king of England with great pomp and circumstance. With him was brought the bruised and battered body of Richard III, his naked corpse slung over the back of a horse. A great amount of abuse was heaped upon his corpse on the journey to Leicester, including dagger stabs to the buttocks so deep that it cracked his pelvis.²² Richard was unceremoniously buried at church of the Greyfriars or Franciscan Friary in Leicester.

Henry Tudor’s party left Leicester and slowly made their way towards London. Along the way, Henry’s mother Margaret Beaufort, now released from her house arrest, met up with them and accompanied them to London.²³ This was the first time she had seen her son in fourteen years. It must have been a glorious reunion filled with relief and thanksgiving.

There has been much debate over the years about the Stanley brothers’ intentions. Most historians believe that Lord Stanley was on the fence as to whether to support Henry or Richard but I find this very hard to believe. First of all, Lord Stanley was married to Henry Tudor’s own mother who was her son’s biggest champion and was determined to see him sit on the throne of England. I think his plan all along was to help Henry, but in order to do so, Lord Stanley would have to stay outwardly loyal to Richard. If Richard found out that Lord Stanley was plotting against him, he would have undoubtedly arrested and beheaded him. That would have left Henry without a champion in England and he desperately needed Lord Stanley for the success of his venture. Lord Stanley was in a very difficult position. To support Henry, he would probably have to sacrifice his son, Lord Strange. So he did his best to try and get both positive outcomes and he actually succeeded. He helped his stepson Henry win the crown of England and kept his son Lord Strange alive. Apparently, Richard ordered the execution of Lord Strange during the Battle of Bosworth but became understandably distracted and did not see that it was carried out.²⁴