Who Really Won the Battle of Bosworth? | History Hit

Who Really Won the Battle of Bosworth?

Phil Carradice

04 Mar 2023

It’s a game historians play – who really won the Battles of Waterloo, Hastings, Agincourt etc. With the Battle of Bosworth Field it’s a particularly apposite debate.

Did Henry win in 1485 or did Richard lose? Either way there is always the nagging thought that it was neither. So, who won the battle? Let me offer you Lord Thomas Stanley.

Husband number three

Within two months of Henry’s birth at Pembroke Castle in January 1457 Margaret Beaufort, his young mother, left the security of the West Wales stronghold and headed east to Monmouthshire.

Jasper Tudor, her brother-in-law, knew that with Margaret’s husband (his brother Edmund) dead, she needed a new husband and her son a new protector.

A first attempt ended in failure when husband number two, Henry Stafford, was executed by Warwick the Kingmaker after the Battle of Edgecote. Husband number three was an altogether more successful choice.

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Lord Thomas Stanley was one of the richest and most powerful men in England. A supporter of Edward IV, it was only after Richard of Gloucester seized the crown in 1483 that he began to have doubts.

Margaret had hitched her star to the Yorkist cause by marrying Stanley but undoubtedly her aim was to obtain a pardon for her son – then languishing in exile in Brittany.

From the beginning of their relationship Margaret could see that Stanley was a prevaricator. He had no love for the usurper Richard but Henry was an unknown alternative.

Nevertheless he allowed Margaret to write secretly to her son, promising his support – and that of his younger brother William – should the last of the Lancastrian princes decide to invade.

The message gave Henry heart, even though the promise of support was indirect and given at second hand.

Quartered arms of Sir Thomas Stanley, 1st Earl of Derby, KG. Image Credit: Rs-nourse / Commons.

Hedging his bets

Henry left Harfleur with his small invasion force on 1 August 1485, having had no further communication from his father-in-law. He trusted Stanley’s word but throughout the march northwards from Milford Haven a lack of further contact with the powerful Stanley continued to plague Henry. When the time came how would his father-in-law jump?

The worry would simply not go away. Henry regularly despatched messages to Stanley, writing or sending out envoys every time his army paused to rest, but received little in reply. When he did respond Stanley was non-committal.

At Machynlleth Henry’s concern was so great that he consulted a local soothsayer about his chances of victory. The prophet gave a positive reply – perhaps understandable with dozens of heavily armed troops around his door. If Henry could have received so positive a response from his father-in-law he would have been deliriously happy.

Without Stanley’s support, Henry’s army would have been greatly outnumbered by Richard III’s royal force.

Richard III takes action

Meanwhile Stanley was receiving threatening messages from the King, demanding that he join him at Nottingham. Pleading illness – the so-called sweating sickness – Stanley stayed away from court which led Richard to take his son George, Lord Strange as hostage.

If Thomas Stanley was annoyed at this his brother William was infuriated, declaring Richard’s action as un-knightly and base. He then declared for Henry. Even so he did not move his troops any closer to the invader and Henry was actually no better off.

When he sent requests for the Stanleys to meet him at Shrewsbury – a Stanley enclave –  there was no reply.

It was not all doom and gloom, however. After refusing Henry entry to the town, the bailiff changed his mind when a message from Lord Stanley was apparently thrown over the wall (wrapped around a stone) ordering the gates to be opened. The unaccountable arrival of Stanley’s son-in-law with 1,000 troops also played a part.

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Aiding from a distance

Stanley’s behaviour continued to puzzle Henry. When he entered the town of Lichfield, he found that Thomas had been there a few days before and had effectively “paved the way” for him. Henry was welcomed by the townspeople as the future King but Thomas Stanley stayed resolutely away.

Stanley had left his castle at Lathom on 15 August and was soon in position mid-way between the forces of Henry and Richard where he could turn whichever way he chose.

Henry and Lord Stanley did finally meet at Merevale Priory on 21 August, the day before the battle, and Henry came away pleased at Stanley’s promises. Jasper Tudor and the Earl of Oxford, Henry’s main advisers, were not.

The Battle of Bosworth

Bosworth Field: Richard III and Henry Tudor engage in battle, prominently in the centre.

When, early on 22 August Henry sent a message asking Stanley to take up his position at the head of the vanguard – as agreed during the meeting at Merevale – the reply was devastating. Lord Stanley would take up his battle position but only when Henry and his troops were actively joined in battle.

Despite his declaration of support, William Stanley also declined to attack at that stage.

Henry gazed at Stanley’s 6,000 troops sitting impotently on his right flank and knew that, outnumbered three to one, he would have to fight Richard without their help. The battle lasted just two hours and the Stanleys stayed inactive for most of it.

They watched as Oxford destroyed Richard’s right wing and then saw the King make his final, fatal charge down the hill towards Henry’s exposed and potentially fatal position.

facts about richard III

Engraving of Richard III charging at the Battle of Bosworth.

Only when it was clear that Henry was in danger did William Stanley, followed by his brother, send in his troops. King Richard was killed, his army scattered and Henry saved.

Richard had been just a few sword lengths from his enemy when he was battered to the ground. Without the timely intervention of the Stanleys the battle could easily have gone the other way.

Phil Carradice is a well-known writer and historian with over 60 books to his credit. A poet, story teller and broadcaster, he is a regular broadcaster on BBC Radio and TV, presents the BBC Wales History programme “The Past Master”. Following in the Footsteps of Henry Tudor is his most recent book, published by Pen and Sword on 4 September 2019.

Tags: Henry VII Richard III

Phil Carradice