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The Battle Of Bosworth Field 1485

In this article we cover the battle of Bosworth field and the events that lead to the battle and the start of the Tudor dynasty.

The defeat at Tewkesbury was devastating to the Lancastrian cause.  Only hours after Edward IV returned in triumph to London, Henry VI was dead in the Tower.  The circumstances of his death were mysterious but the execution of his supporter the duke of Somerset was an open warning.  Jasper Tudor had good reason to fear for both his and Henry’s safety.  Margaret Beaufort and her husband almost immediately declared allegiance to Edward to protect themselves.  But her son, as one of the few surviving males with Lancastrian blood, was destined for France.  Jasper hoped that their old ally Louis XI would aid them once again.

Before he arrived in France, however, he fought a battle in Wales at Chepstow.  Edward IV was still determined to capture him and sent Sir Roger Vaughan to do so.  Jasper Tudor managed to defeat Vaughan and executed him.  This ruthless act was uncharacteristic for Jasper but can be easily explained – Vaughan had killed his father, Owen Tudor, almost ten years before at the battle of Mortimer’s Cross.  The satisfaction of this execution was Jasper’s only comfort as he fought his way to the coast.  From there, he, his nephew, and a few servants made their way to France.  They ended up landing in Brittany, where the duke Francis II had long supported them.  Francis was desperate to preserve his duchy’s independence from the French state and recognized Jasper and Henry as powerful diplomatic tools.  If Edward would aid him, then perhaps he would return the Tudors – that was Francis’s official diplomatic message.  Edward made several attempts to gain custody of the Tudors but was unsuccessful.  His concern, however, was intermittent since they were not in England and he was more concerned with his own family and rule.

From 1471 to Edward’s death twelve years later, Jasper and Henry remained in Brittany, staying at the castle of Suscinio, traditionally used as the duke’s summer residence.  Louis XI of France, meanwhile, was engaged in more diplomatic rivalry.  Resenting Edward’s relations with his enemies, he sought the release of Jasper and Henry into his custody.  He told the duke of Brittany that the Tudors had, after all, intended to go to France itself – their landing in Brittany had been a mistake of bad weather.  Also, Jasper had been given a pension by Louis during their earlier stay; consequently, he was a servant of the king and under his protection.  Both men wanted to use the Tudors as diplomatic pawns but Francis II was unwilling to give up his advantage.  The Tudors stayed in Brittany, under increasingly strict control.  There were reports that Edward IV wanted Henry killed and that Louis XI was going to kidnap them.

Edward IV had to console himself with Francis II’s promise that the Tudors were under protective custody.  In the mid-1470s he tried a new strategy, with the aid of Henry’s mother.  She had extracted a promise from the king that some of her lands would pass to her son on her death.  Edward not only agreed but he also suggested an English bride – perhaps one of his own daughters – for the exiled earl.  Margaret Beaufort gave her full support to this plan.  She wanted her son in England above all else.  Whether Edward intended to keep his promise is unknown but it was certainly a good idea.  By marrying Henry into his family, he would neutralize this last Lancastrian threat.  And, for a while, it seemed he would be successful.  In late 1476, worn down by ill health and the English ambassadors, Francis II consented to send Henry to England.  Henry developed – or faked – an illness at the port and was able to elude being sent home.  It may be that he suspected duplicity on Edward’s part or was counseled by his uncle.  (It seems evident that Henry, the first Tudor king, shared many qualities with his granddaughter, Elizabeth I, last of the Tudor monarchs – both were shaped by perilous upbringings into cautious, careful rulers.  In truth, they bore little resemblance to Henry VIII, Edward VI & Mary I.  They were also far more concerned with domestic policy than foreign entanglements.)

Since Henry had, by now, grown into a handsome and affable teenager, he was always welcome at the ducal court.  After avoiding being sent to England, he simply returned to the duke’s custody.  There, he continued to be treated fairly – indeed, even generously.  Every now and again, Edward IV and Margaret Beaufort tried to lure him to England (for different reasons, of course.)  Margaret had asked Edward to let Henry stand as heir to her estates and he agreed (in 1472) but by 1482, Edward IV decided this – if Henry returned to England and gained Edward’s favor, he would receive Margaret’s lands plus other estates.  But if he stayed in France, he would get nothing.  Nothing had been decided when Edward died unexpectedly on 9 April 1483.  By this time, Duke Francis was facing instability in his own lands.  Naturally enough, this made Henry and Jasper’s position more tenuous.  Still, they received as much support from the duke as he could provide, including generous gifts of money.

It may be that, upon Edward’s death, Henry seriously thought of returning home.  The events which followed the king’s demise certainly set him upon that course.  As recounted earlier, Richard duke of Gloucester, seized the throne from his nephew, Edward V, his brother’s 12-year-old heir.  Richard officially seized the throne on 26 June.  There was no immediate effect on Henry and Jasper Tudor.  But their protectors, the French king Louis XI and Duke Francis II, immediately recognized the possibilities – after all, Richard III’s claim was tenuous and he would need to work out some arrangement regarding other claimants.  Jasper and Henry Tudor would bear even greater pressure on Richard than they had on Edward.  At first, Richard simply tried to establish friendly relations with the king and duke, without explicitly mentioning the Tudors.  His more immediate concern was the closing of French ports to English exiles (notably former Queen Elizabeth Woodville’s brother and a large section of the English fleet.)  In England, Margaret still wanted her son to return – though to his rightful position as earl of Richmond, not as king of England.  But events soon changed, with the same rapidity of Richard’s usurpation, and Henry Tudor dreamed of more than an earldom.

Richard III’s usurpation was bad enough to most Englishmen, and especially the nobility.  But in 1483, Edward IV’s two sons – held in the Tower – mysteriously died.  It was whispered that Richard had them murdered and secretly buried.  Thus was born the legend of the ‘Princes of the Tower‘.  (What happened remains a matter of conjecture; mystery novelist and playwright, Josephine Tey, wrote The Daughter of Time, a book which convincingly argues for Richard’s innocence.  In that case, Henry VII executed the boys – who would be his brothers-in-law – in order to secure his throne.  More recently, the lawyer Bertram Fields examines the case in Royal Blood.)  The deaths of Edward V and his brother, Richard duke of York, angered the populace and encouraged the image of Richard III as a deceitful murderer.  Since Richard never officially responded to the rumors, they were believed to be true.  Soon enough, the duke of Buckingham, Henry Stafford, created more chaos.  He led a rebellion against Richard III in October and was captured and executed in November.

First of all, it is important to remember that Buckingham, Richard III and Henry Tudor were the only surviving male heirs to the house of Plantagenet.  The reasons why Buckingham led a rebellion against Richard are not clear but several possibilities can be considered – first, he had as legitimate a claim to the throne as Richard and, gauging popular dissatisfaction with the new king, Buckingham felt he should take his chances and set himself up as the rival claimant (particularly since Edward V and Richard of York were supposedly murdered); second, as a rival claimant, Buckingham undoubtedly felt uneasy about his own safety (particularly when it was rumored Richard had murdered his two nephews; if he had, it was possible he would decide to murder Buckingham as well.)  These two reasons alone are sufficient to explain Buckingham’s motivations.  Later historians, especially Polydore Vergil (Henry VII’s official historian) would later claim Buckingham really intended to defeat Richard and place Henry Tudor on the throne.  But it hardly seems likely; indeed, Buckingham could legitimately believe he had a more solid claim than Henry.

There had been uprisings against Richard III just days after his coronation which highlighted popular dissatisfaction.  Meanwhile, Margaret Beaufort had become friends with Edward IV’s widow, Elizabeth Woodville (or Wydeville).  Elizabeth heard the rumors of her sons’ deaths in the Tower; she had no way of gauging their truth.  But she was eager to reassert her family’s claim to the throne.  With her sons supposedly dead, that left her five daughters – in particular, her eldest Elizabeth of York – to claim the throne.  They could do so only through marriage to a male claimant (such as Henry Tudor.)  So the plan to wed Elizabeth and Henry began in earnest.  Both women knew that such a marriage would imply that Henry Tudor wanted to replace Richard on the throne.  Margaret quickly sent Christopher Urswick, a young priest from her household, to Brittany.  her son, so long an exile and dependent on others, was to plan a return to England – to claim two great positions, husband and king.  Margaret also sent a large sum of money to her son, raised from loans in London.  She advised him to come to Wales as soon as possible (since he would receive support in Wales, particularly from the duke of Buckingham.)

This, of course, lends credence to the idea that Buckingham wanted to support Henry’s claim.  But, again, that is conjecture.  Buckingham did write a letter to Henry on 24 September 1483 which stated he would support the rebellion against Richard, even though he and Henry’s interests may not be perfectly compatible.  What is certain is that Buckingham suspected his own life was forfeit with Richard III; he and Henry Tudor could sort out things once Richard was defeated.  He told Henry the rebellion would begin on 18 October, thus giving Henry three weeks notice.  He did not mention acknowledging Henry as king – he also did not mention marriage to Elizabeth of York.  Henry received Margaret and Buckingham’s letters and talked with the duke of Brittany.  He needed further financial support but also relied on Francis’s advice.  The duke promised support; another vital link was established.

Richard III had not suspected Buckingham of treachery – at first.  Thus, he had no large army assembled to fight the duke.  But such a massively-planned uprising could not remain secret forever and Richard was informed on 11 October that a vast rebellion would occur in a week.  He had heard vague descriptions of a plan a few weeks before and had summoned Buckingham to him.  The duke feigned a stomach ache; a more tersely-worded summons soon followed.  The duke again refused the summons.  By then, the rebellion was a week away and Richard had been informed of Buckingham’s involvement and the extent of the rebellion.  Richard hurriedly assembled his army; and though he had been betrayed by Buckingham, his former friend, he was not bitter – he specifically ordered his troops to not ‘rob, spoil or hurt’ any of Buckingham’s followers.  Richard was prepared to be merciful.

Buckingham’s rebellion began – and failed, largely because his Welsh tenants decided they liked him less than Richard III.  Robbed of this crucial support, he fled to a friend’s home but the friend, Ralph Bannaster, turned him in and, on 31 October, Buckingham was taken to Sir James Tyrell and Christopher Wellesbourne, staunch supporters of Richard III.  Once Buckingham had been captured, the other rebellions collapsed.  Many of the rebels fled to Brittany, to join Henry Tudor, now their last hope.  Richard III attempted to prevent this mass exodus of rebels but failed.  Meanwhile, at Plymouth Harbor, Henry heard the news of Buckingham’s execution on 2 November 1483.  (He had been delayed on his way to England because of a storm.)  His other rival for the throne had been killed (Buckingham’s son and heir was just six years old) but Buckingham’s failure was hardly encouraging.  He returned to Brittany, once more an exile after twelve years abroad.  His position was perhaps more untenable than before – the uprising had been soundly defeated and Richard III was once again making friendly overtures to duke Francis.

Henry’s only hope lay with the English exiles now joining him in Brittany.  There were roughly 500 men, among them the marquess of Dorset.  These exiles told him he must reassemble his allies and attack again, before Richard III became more firmly entrenched as king – and before the duke ended his hospitality.  In December, Henry gave a speech at Rennes Cathedral meant to boost morale and inspire his supporters.  He promised to marry Elizabeth of York, thus joining the houses of York and Lancaster together.  The assembled men swore oaths of loyalty to him.  Their next task was more difficult – persuading the duke of Brittany to lend them more money to assemble yet another fleet.  Again, Henry promised to repay the money.  He was fortunate that Richard III had decided to retaliate against Breton and French ships because of their assistance to Henry and Buckingham.  The duke was angered and agreed to loan Henry more money.  So another flotilla was assembled and final preparations made in mid-spring 1484.  But, for some unknown reason, the exiles did not sail for England.

Instead, they remained at Vannes in Brittany.  By this time, Henry fully realized the enormous stakes of the enterprise.  He was particularly moved by the loyalty of the other exiles.  Many were separated from their families and all were wanted men – and they suffered these injuries to support him.  He owed them a great debt and it is to his credit that, immediately after Bosworth, he rewarded them.  Elizabeth Woodville’s son by her first husband, the marquess of Dorset, was in Brittany as were her three brothers, Lionel, Edward and Richard.  They were joined by many loyal servants.  All of the exiles were undoubtedly horrified by the supposed murders of Edward V and Richard of York.  While these men schemed with Henry Tudor, the object of their schemes – Richard III – attempted to nullify their threat.  He tried various tactics, mixing friendly overtures with veiled threats.  He knew Margaret Beaufort had sent messages to her son and plotted in the rebellion but he couldn’t risk alienating her husband, Lord Stanley.  So he told Stanley to watch his wife carefully, dismiss the servants who had relayed messages, and prevent any contact with Henry and other rebels.  He also gave Stanley possession of Margaret’s property for the course of Stanley’s life; after his death, the lands would pass to the crown.  Still, Margaret had every reason to be grateful for her life.

In March of 1484, Richard attempted a reconciliation with his former sister-in-law, Elizabeth Woodville.  She and her five daughters had sought sanctuary in Westminster.  Richard gathered the lord mayor of London, all leading aristocrats and various aldermen to his palace.  He announced that – if Elizabeth and her children left sanctuary – he would protect them; they would be recognized as his kin and given a pension and dowries.  Most importantly, he publicly promised they would not be sent to any prisons, including the Tower of London (the site of their brothers’ deaths.)

He also attempted to win over the duke of Brittany again.  In this he was aided by the ailing duke’s treasurer, Pierre Landais.  Landais believed Brittany’s fate would be better served with an English alliance.  It could be, too, that he disliked the assembled rebels.  As a result, Henry asked the French king Charles VIII for asylum at his court.  Charles agreed and, soon enough, Henry left Brittany for Paris.  It was a dangerous decision and, as it was taken without Francis’s permission, would have resulted in his arrest.  But he managed to arrive in Anjou with his pursuers just an hour behind.  (His uncle Jasper had left a few days earlier, ostensibly to visit Francis at Rennes.  Both he and Henry turned away at the last moment and headed toward Anjou.)  There were about 400 rebels left behind.  Duke Francis certainly had every right to send them back to England, to face certain death.  But he did not – sick as he was, he was determined to undo some of Landais’s damage.  He allowed the rebels to join Henry in Paris. He also gave them a large gift of money (about 700 livres) to pay for their travel (this was in addition to their living allowance he was also paying!)  Henry Tudor was touched by his old protector’s kindness and generosity.  He sent a letter of thanks, realizing that the treachery had been Landais’s and not the duke’s.

Of course, the French royal family were very eager to use Henry as a diplomatic weapon against the English.  But the situation at the French court was confused and problematic; in the end, Henry relied upon the king’s older sister, Anne of Beaujeu, for assistance.  Her role was of vital importance as Henry planned for the greatest battle of his life, Bosworth Field.


The French court which welcomed Henry Tudor was a curious place.  King Louis XI had died on 30 August 1483, leaving behind a thirteen-year-old heir who became Charles VIII.  As often happened when a minor succeeded to the throne, a power struggle ensued between the new king’s relatives over the role of regent.  Charles’s mother, Charlotte of Savoy, was not a serious contender; she had never been involved in politics and was seriously ill.  (She died on 1 December.)  So the struggle was between Charles’s older sister, Anne, and his younger sister’s husband, Louis duc d’Orleans.  Anne was twenty-two years old and married to Pierre, Lord Beaujeu, the heir of the duc d’Bourbon.  Anne triumphed over her brother-in-law Louis and her gained control of the government.    Henry Tudor’s former patron, Duke Francis II, soon became involved in this struggle – at least ostensibly.  His servant Pierre Landais (discussed on the previous page) was hated by the Orleans party who were seeking an alliance with his old enemies – namely, the noblemen of Brittany who had fled during Landais’s ascendancy.  (Naturally enough, they had fled from Brittany to France, where they met with the Orleans party.)  On 7 April 1484 these new allies attempted to destroy Landais, breaking into the ducal palace at Nantes and then going to his country house.  They failed to find Landais, however, and were forced to flee in shambles.  They waited at the town of Ancenis, in Brittany but near the French border.  Landais remained in power and seemed to bear no ill will toward the Breton-Orleans conspirators.  In autumn, the Orleans party attempted – once again – to make peace between Francis II and his exiled noblemen.  This time, they didn’t attempt to kidnap Landais as part of their plan!  Landais was a pragmatist and undoubtedly wanted to rid himself of the troublesome Breton-Orleans scheming.  So he supported their plan; in doing so, he knew he would anger the French monarchy.  Naturally, he turned to England’s King Richard III for assistance, asking that Richard recognize the Orleans-Breton alliance; in return, Landais offered to send Henry Tudor to England.  (Landais would then have the support of Burgundy, Orleans, and England against any French designs on Brittany.)

Of course, Henry Tudor fled to France where he was welcomed with open arms.  With Henry Tudor gone, Brittany had no olive branch to offer England; this would weaken the Breton-English alliance.  It would also aid Anne of Beaujeu in her struggle against the Orleans party.  When Henry arrived in Anjou, he sent a messenger to Charles VIII, then at Montargis.  The king immediately sent an envoy to greet Henry and bring him to Chartres.  The envoy was given the generous sum of 20000 francs for expenses on the week-long journey.  Charles was, of course, delighted to encourage Henry in his plan to overthrow Richard III – though less delighted to give him large sums of money on a continual basis, as Duke Francis had.  Also, Charles may have been unnerved by the large number of Henry’s English followers who needed to be housed and fed while awaiting developments.  Charles did give Henry about 3000 francs to clothe his army and granted permission for Henry to assemble mercenaries for his army.  Henry traveled with the king north to Paris (the court spent autumn in the beautiful Loire valley); on 4 February 1485, they reached the French capital.  During this journey, Henry finally realized the necessity of immediate and decisive action.  He had spent nearly fourteen years as an exile in France and Landais’s betrayal revealed the instability of his position.  What if Anne of Beaujeu fell from power?  Would he be a pawn for the Orleans cause?  Also, it is true that Henry was in his late twenties, strong and healthy and undoubtedly yearning to be his own man.  Why would he want to live in other people’s homes, dependent on their good will and generosity?

Richard III was certainly unhappy with events in France.  He sent word to Charles of his displeasure and also tried to rally English support against Henry.  Henry was sending letters to England during the winter of 1484-5 to inspire potential supporters (since many were dissatisfied with Richard’s rule, for reasons outlined in previous pages.)  Richard was aware of these letters and ordered the mayors and sheriffs throughout England to arrest anyone receiving or distributing them.  (One of the letters has survived – click here to read it.)  An interesting note about these letters – Henry was styling himself King of England, a deliberate and flagrant disregard of Richard’s position.

On 7 December 1484, Richard responded to the letters by sending out his own proclamations.  He condemned the exiles supporting Henry in France; he also mocked Henry’s use of the royal title.  He also reiterated the ancient animosity between England and France, reminding the English people that – in exchange for Charles’s support – Henry had supposedly promised to return the English possessions in France and relinquish the traditional English claim to the French throne.  These, of course, were matters near and dear to all English hearts.  From the 12th century onwards, the English claim to the French throne and territories was a patriotic dream shared by all Englishmen.  The great heroes of the past (most gloriously, Henry V) had led their countrymen to battle over those claims; thousands of Englishmen died in those battles.  By painting Henry as a traitor to one of the most precious English dreams (that of possessing France), Richard hoped to appeal to English patriotism.  He also reminded his subjects that Henry would be invading with mercenaries who would commit ‘the most cruel murders, slaughters, robberies and disinheritances that were ever seen in any Christian Realm.’  Once again, Richard appealed to a time-honored English abhorrence of invasion.  He also attended to more practical matters – ordering sheriffs to prepare troops for muster and raise cash for military payments.

I would like to emphasize – once again – the tenuousness of Henry Tudor’s claim.  At this point, only he and Richard III were viable claimants to the English throne.  But Richard’s position was stronger by far (and as will become clear later), the Battle of Bosworth ended in Henry’s favor only because a key nobleman betrayed Richard.  This was hardly an auspicious beginning to Henry’s rule.  Throughout these pages, I have tried to emphasize the general unpopularity of Richard’s rule – with regard to the disappearance of his nephews.  The disappearance sullied Richard’s character and made those Englishmen who didn’t support Henry Tudor less than thrilled about defending Richard III.  In other words, they would simply wait out the conflict without openly supporting either party.  And that is exactly what most of the country did.  Personally, I do not believe Richard III murdered his nephews but, of course, the mystery will always remain open to interpretation.  It is true that Richard III has received a ‘raw deal’ from historians.  Can we blame this on Shakespeare?  🙂  Hey, it is a great play but written during the reign of Henry Tudor’s granddaughter.  It isn’t likely the playwright wanted to offend the monarch (witness the ending to All Is True for proof of that – a sympathetic introduction to Katharine of Aragon which ends with Elizabeth’s triumphant birth.)  Richard was a capable and intelligent man and – whatever the truth about his nephews – had far more experience in government than Henry Tudor.  He also reacted to betrayal with an appealing mixture of punishment and forgiveness; he was far more conciliatory than, say, Henry VIII.  (During this time, an embarrassing episode occurred which may have furthered Richard’s resolve to shore up his support against Henry:  John de Vere, the Lancastrian earl of Oxford, was imprisoned at Calais in France; he escaped, along with two English soldiers, to join Henry Tudor in Paris.  Understandably, this embarrassed Richard; he issued pardons to the English soldiers at Calais, including de Vere’s supporters, but they still rebelled.  In the end, Henry’s morale went up and Richard’s fell drastically.  The Oxford episode indicated the lack of loyalty to Richard’s regime.  This was coupled with the disloyalty of Sir William Stanley, advising Henry from England.)

Of course, these domestic actions were accompanied by foreign policy initiatives designed to find Richard prominent allies.  In this, he was successful as well.  Henry Tudor’s old ally, Duke Francis of Brittany, entered into a seven-year truce with England on 2 March 1485.  One of the specific points of the truce was that neither side would support rebellion against the other, thus allying Richard and Duke Francis against the French throne.  Not surprisingly, Charles VIII began to fear an English-Breton invasion of France. So he encouraged Henry Tudor to hasten his plans to invade England.  In March 1485, Richard’s queen, Anne Neville, died and this personal heartbreak had to be shoved aside in the face of Henry Tudor’s rebellion.  It was soon rumored that Richard would marry Elizabeth of York or her sister Cecily, thus regaining the support of Henry’s Yorkist allies.  Henry, whom Elizabeth Woodville and Margaret Beaufort intended to wed Elizabeth, was upset but could do little.  Meanwhile, Richard kept a shrewd eye on Lord Stanley (I’ll let you alert readers figure out the Tudor-Stanley connection from the earlier pages – here’s a clue: who was Margaret Beaufort married to?)  Around July 1485, Stanley asked permission to visit relative in Lancashire.  The king was no fool; he allowed Stanley to leave London but kept his son and heir, George, Lord Strange, as hostage.  Essentially, Strange remained in Richard’s household in order to assure his father’s good behavior.

Charles VIII was, of course, still encouraging Henry’s planned invasion but still hedging about financial support.  When news came that Richard might marry Elizabeth of York, Henry became frantic.  He cast about for another prominent Yorkist bride, with little success.  More importantly, (with the support of Philippe de Commynes, an influential diplomat) Henry pressed Charles to request money from the French parliament.  The French king did so on 4 May 1485 and was successful; he returned with Henry to Paris about a month later.  Already, plans to assemble an invasion fleet were being approved.  At Harfleur, near the mouth of the River Seine, Henry spent about 50000 livres to assemble 4000 men.  Of these, 1500 were discharged soldiers from a base at Pont de l’Arche.  The French soldiers were commanded by a nobleman from Savoy called Philibert de Chandee, who later became a good friend of Henry Tudor’s.  There were also Henry’s 400 English supporters who had shared his exile.  Henry placed these men under the command of Richard Guildford.  (It was later rumored that about 1000 Scots joined Henry’s force; whether that number is correct or not, some Scots did fight on Henry’s side.)

Henry’s great enterprise was about to begin.  On 1 August 1485, Henry and his followers left Honfleur and sailed down the Seine into the Channel.  On 7 August, they sailed into Milford Sound near sunset.  They actually landed at Mill Bay, inside the Sound.  This was the land of Pembrokeshire where Henry had been imprisoned as a young man.  Upon landing, Henry knelt down and whispered, ‘Judge me, Lord, and fight my cause.’  He kissed the English soil, crossed himself, and told his men to follow him – in the name of God and St George.  It was no coincidence that he landed in Wales, his father’s native land; it was there that he hoped to gain crucial support for his cause.


(NOTE:  Historical sources regarding the actual battle at Bosworth are scanty at best.  No one who actually fought at the battle recorded the battle; typically, the chroniclers from London recorded great events but they were far from the action in 1485.  Also, the supporters of Richard III didn’t want to remember their defeat – and unlikely to write about in the charged political climate.  Henry’s supporters were concerned with more immediate matters after the battle – namely, beginning the rule of a very inexperienced monarch who had not been to England in fifteen years.  And there is another very important fact – medieval battles are incredibly confusing to describe (just as they were confusing to fight.)  Imagine a Revolutionary War battle – the British soldiers in matching red coats, marching in perfect cadence to a fixed point, they shoot, reload and aim with some degree of consistency.  Medieval warfare did not proceed along those lines.  In general, it was chaotic and confusing to the participants – and the chroniclers.  So if the following account confuses you a little, you’re in good company.  I have tried to be as clear as possible, to the extent of omitting stuff which is particularly confusing (including Henry’s mysterious ‘disappearance’ the night before the battle; that will eventually be included in the Primary Sources section, directly from Polydore Vergil’s work.
The most prominent chronicler of the Battle was Polydore Vergil, Henry VII’s official court historian.  Of course, his version is the official Tudor account but we must rely upon it.  In most respects, Vergil had little reason to alter anything since the Tudor claimant was victorious.)
Henry’s force marched to the nearest inhabited area, a settlement called Dale.  There they spent the night; the next day (8 August) they left Dale to a castle called Haverfordwest, about 12 miles to the north-east.  The townsmen actually welcomed the invaders, an indication of their nebulous loyalty to Richard III.  Of course, news of Henry’s arrival on English soil was only just spreading along the coast.  In this northern part of Pembrokeshire, there were fewer castles and – again – it was Jasper Tudor’s former home.  Also, Richard III had extensive control over south Wales, which shows that Henry’s Welsh support was as nebulous as Richard’s English support.  Richard’s control over much of Wales also meant that Henry was forced to march north into the center of Wales.  And, of course, it must be recalled that the Stanleys (his mother’s in-laws) controlled much of north Wales and Cheshire.  Sir William Stanley was Richard III’s chief lieutenant in Anglesey, Caernarfonshire, and Merioneth, cities which made up the northern part of royal holdings in Wales.  (Remember that Sir William was the younger brother of Henry’s stepfather.)  Henry may have been in touch with the Stanleys immediately upon landing in Wales.  Oddly enough, a letter Henry sent to another supporter, John ap Maredudd ab Ieuan ap Mareddud, has survived; it was written about 8 August, immediately after the landing, and designed to gain Welsh support.  The letter to ap Mareddud can be read by clicking here.  What did ap Mareddud do?  We don’t know – though it is true that Henry did have some significant Welsh support.  Of course, it was nowhere near as great as many later remembered.  And it is false to state that every Welshman welcomed the return of Owen Tudor’s descendants.  Certainly the Tudor dynasty in no way favored Wales or its native population – so any support from the Welsh was not rewarded.  In 1536, in particular, the Welsh had good cause to resent any support they had given.  After Bosworth, certain laudatory poems and songs were written – but as these were dedicated to an actual king than a pretender to the throne, they were naturally fawning.

    In reality, Henry did not receive a rapturous welcome.  On 8 August, at Haverfordwest, he received a crushing blow – John Savage, nephew of Henry’s stepfather, and the powerful Welsh lord, Rhys ap Thomas, were not planning to support his cause.  Of course, they had promised otherwise while he was in France but Richard III suspected both men of disloyalty – and before Henry landed, he made certain they understood the penalty of treason.  With this crushing news, even the professed loyalty of Pembroke was small consolation.  Henry’s march from Havefordwest northeast to Cardigan and there to Machynlleth (about 100 miles from the Dale settlement) is not documented.  He arrived at Machynlleth on 14 August and wrote a letter to Sir Roger Kynaston, the guardian of the Grey estates; to pass safely to Shrewsbury, Henry needed – at the very least – Kynaston’s inaction.  The guardian didn’t need to declare for him but he could at least not impede his progress. Click here to read the letter to Kynaston.  Whatever Kynaston’s decision, Henry did pass safely through to Shrewsbury.  To get to this point, his force had marched through the mountains of Wales but they had the continual arrival of good news to cheer them on the lonely journey – supporters were marching to join them, bringing along much-needed supplies.  Among these supporters was Rhys ap Thomas, who finally decided to honor his previous promise.  Rhys later said he brought almost 2000 men with him; if true, his force made up a third of Henry’s entire army.  They were in time to join Henry at Shrewsbury, the traditional gateway to the English midlands; they marched along the old Roman road even as supporters sent along money to pay the mercenary troops.  But at Shrewsbury, Henry’s progress was no longer easy.

    Shrewsbury was an important town and had two bailiffs, Roger Knight and Thomas Mitton, both in power for about two decades.  They had prospered under Richard III, notably from the failure of Buckingham’s rebellion (notably, Mitton received Buckingham’s castle and Shrewsbury’s tax bill was significantly reduced.)  And one must remember Richard III’s admonitions to the English people, specifically warning them of the dangers of mercenary troops.  The people of Shrewsbury had no desire for foreign troops to plunder and pillage their town.  (Keep in mind that Henry’s army was not primarily English.)  When Henry requested permission to march through the streets, Mitton made a familiar reply – “over my belly.”  Henry could not afford to go around the city so he retreated.  At a nearby village, he composed a letter to the bailiffs, promising that his men would simply march through Shrewsbury peacefully, without causing any damage or harm.  He respected the oath of loyalty to Richard III and did not expect any of the townspeople to break it.  The letter may not have swayed the bailiffs but the arrival of Rowland Warburton, a retainer of Sir William Stanley, arrived and persuaded the bailiffs to let Henry pass.  The Stanley support was impressive enough to sway even Mitton, who lay on the ground so Henry could step over his belly (thus keeping his former oath.)

    What effect did this ‘adventure’ have on Henry?  He realized, once again, that his support was not widespread.  Indeed, in the end he relied upon the apathy of the English population – essentially their decision to not actively support Richard III.  Shrewsbury was the first English town he marched through, a test of how the average citizen would respond to his invasion.  Since they did not recognize his claim to the throne, Henry had little to celebrate.

    In a way, his march was as much a public relations enterprise as a military endeavor.  Everywhere he went, he attempted to drum up support – and he was often successful.  More men and prominent lords joined the cause, all for various reasons.  At Stafford, Henry met up with Sir William Stanley.  Stanley brought news that Richard III, informed of Henry’s march, was camped at Nottingham.  From there, it was just a brief march south to block Henry’s path to London.  In other words, Stanley was urging Henry to hurry if he wanted to reach the capital.  Henry marched to meet Richard, stopping for the night at Lichfield; as at Shrewsbury, he kept his army outside the walls so as not to offend the citizens.

    Now it gets a bit confusing: Lord Stanley, whose son Lord Strange was Richard’s ‘hostage’, was marching with about 5000 men toward Lichfield (presumably to meet up with Richard III at Nottingham.)  He did not dare meet with Henry Tudor, though he supported his claim.  Ostensibly, Lord Stanley was loyal to Richard.  So he avoided Henry’s army though, supposedly, sent a message assuring him of eventual support.  Of course, promises can be easily broken and Henry was uneasy.  He knew Richard had scouts watching Stanley and held his son hostage.  Under such circumstances, Stanley’s support was not completely assured.  Meanwhile, Lord Stanley’s brother – Sir William – had met up with Henry’s army at Lichfield on 20 August.  Lord Stanley had arrived near Atherstone, close to the actual battlefield.  On this Saturday (20 August, still!), Lord Stanley sent his brother a message that Richard was near and fighting could begin in just three hours.  This, of course, did not happen.  But the Stanleys apparently met together and decided on a course of action – namely, they would not publicly declare their support for either Richard or Henry.  On Sunday, they apparently decided upon their battle plans – namely, Lord Stanley’s betrayal of Richard.

    Lord Stanley was, of course, Henry’s stepfather but his waffling is understandable.  But it caused both Richard III and Henry a great deal of anxiety.  Henry secretly met with the Stanleys on 21 August but, after the meeting, was still unsure of their unqualified support.  Under such circumstances, Henry’s nervousness was greater than the king’s.  But Richard was far from secure himself.  He was at Nottingham when he heard of Henry’s arrival in Pembrokeshire and, from there, his steady march through Wales to the midlands.  As mentioned earlier, Richard had made preparations for this moment in 1484.  So he ordered his nobles and gentry to assemble according to plan.  He was undoubtedly unnerved that Henry was receiving some measure of support and that his march was essentially unimpeded.  He called the dukes of Northumberland and Norfolk to him, as well as the lieutenant of the Tower of London (where most of the king’s weaponry was stored.)  Because Sir William Stanley did not respond to summons, Richard declared him a traitor.  He also intimidated Lord Strange enough for the young man to confess to some sort of ‘conspiracy’ to betray the king.  This simply confirmed Richard’s fears.  He realized as well that Henry was trying to reach London as quickly as possible.  So he gathered his own forces to prevent this; he was later called a coward for not confronting Henry sooner but consider this – Richard wanted to assemble as many supporters as possible while dragging out the ordeal for Henry’s army.  The assembled mercenaries were tired, hungry, and – like Henry – knew the crucial Stanley support was not secure.  Richard’s army was a bit larger than Henry’s though exact figures do not exist.  They marched south in traditional square battle formation, Richard and his guard behind two groups of horsemen.  There were about 100 knights and noblemen who had responded to Richard’s summons.  Most of these men were from the north, specifically Yorkshire and Lancashire.  Richard marched with these men as the King of England, wearing his crown and coat-of-arms.  It was imperative that every Englishman who watched the march be reminded the Richard was the king and Henry just a pretender.  He would be crushed just like the duke of Buckingham.

    Finally, on 21 August (Sunday), both armies knew battle was near.  Richard knew Henry’s camp was near Atherstone; he himself camped at the plain of Redmoor.  The next day the forces would meet on the battlefield, a place later called Bosworth Field.


(I wanted to point out an interesting fact about Henry’s tactics prior to Bosworth; by marching toward London, he essentially determined where the battle would be fought – wherever he and Richard met up on the way to London.  So Bosworth Field was not chosen for any purpose other than the two armies met there.  Today, it is impossible to adequately understand the geography of the battlefield and Richard and Henry’s camps prior to the battle; hundreds of years of building, etc. have altered the landscape.)
(Also: William Brandon, Henry’s standard bearer, was slain at this battle.  His son, Charles, would become Henry VIII’s best friend, husband to Princess Mary Tudor & grandfather of Lady Jane Grey.  His biography is available at Tudor Citizens.)

The Battle of Bosworth Field

The actual battle supposedly took place on Redmoor plain, near Richard III’s encampment.  Long after the battle, it came to be called the Battle of Bosworth Field because the town of Market Bosworth lay to the north of Redmoor plain.  Also, a Welsh chronicler asserted that the battle actually took place at the town.  In other words, there is some debate about where the battle took place – though one can reasonably assert it occurred at Redmoor plain.

Sunday 22 August began inauspiciously for Richard III and one of his most powerful allies, the duke of Norfolk.  Richard admitted he had slept little and suffered bad dreams; in the superstitious medieval world this did not bode well.  Also, the duke of Norfolk found a sign outside his quarters which read, ‘Jack of Norfolk be not so bold, For Dykon thy master is bought and sold.’  After his sleepless night, Richard arose earlier than even his chaplain (so there was no morning mass) and had no breakfast.  He insisted on wearing his crown throughout the day, as he had insisted upon marching to Redmoor clad in his ceremonial robes and crown.  Henry Tudor had spent a sleepless night as well, and his morning began with disturbing news.  His stepfather, Lord Stanley, was still officially part of Richard’s force.  In fact, Stanley’s force waited between Henry and Richard’s camps.  But when Henry pushed his stepfather to join him, Stanley still demurred (this on the day of the battle!)  One can imagine Henry’s response.  Stanley sent Henry a brief message; he should prepare his army for battle and wait for Stanley to join him at the appropriate moment.  (Note: Richard’s archers were under the command of the duke of Norfolk while Henry’s archers were under the command of John de Vere, the earl of Oxford.  The actual make-up of each army is a matter of debate as well, as is their size.  They each had a number of infantry and cavalry, complemented with cannon and guns and – of course – the traditional bows and swords.  One chronicler estimated Richard’s cannon at 140; Henry had cannon brought from France.  As to the actual numbers involved, chroniclers are always prone to exaggeration and this time was no exception.  We know Henry landed in Wales with about 4000 and was joined by a large number of reinforcements; Richard’s force must have been equal – at least.  Sir William Stanley led about 3000 troops.)

One more mention of the Stanleys: Richard was less troubled by their waffling than Henry.  After all, Richard would have been content if they simply stayed out of the battle whereas Henry was desperate for their support.  Therefore, Richard’s army had higher morale – and supposedly larger numbers.

Henry marched northeast at a leisurely pace toward Richard’s camp.  Were his troops wary of attacking first?  Undoubtedly; but, in the end, Richard decided to order his attack when Henry’s force passed by a march.  At this time, he also realized that Lord Stanley was not joining him.  (He could see Stanley’s army motionless on the field.)  Richard ordered his hostage, Lord Strange, beheaded but in the heat and confusion of battle, the order was not carried out.  The first moments of battle were an indication of the chaos to come.  Immediately, arrows were exchanged and then hand-to-hand combat began.  Swords, pikes, aces, spears….  These were the weapons of choice.  (Interesting note: Richard’s ally, the duke of Northumberland, waited at the rear of the army with a well equipped force which never entered battle for one simple reason – the topography of the battlefield.)

Richard’s scouts told him that Henry, too, remained outside the fighting, observing the battle with a small group of supporters.  By identifying Henry’s standard, Richard determined his exact position.  Then he undertook a most courageous and incredible feat – he spurred his horse to ride directly at Henry, the pretender to his throne.  He knew that if Henry was slain – before Stanley intervention – the battle would end.  On his horse, at full gallop, he slay a great number of those around Henry (notably his standard bearer, William Brandon, and that respected soldier, the ‘giant’ John Cheyne.)  Henry, of course, was innocent of real experience in battle but he did not run – though he also kept a horse nearby in case the battle was lost.  Still, the tide would have turned against Henry except….  the Stanleys finally entered the battle, on the Tudor side!

It cannot be emphasized enough that Richard III died valiantly in battle.  Every later chronicler asserted his bravery and skill.  One wrote that, after Stanley’s men swarmed around him, Richard fought ‘manfully in the thickest press of his enemies.’  According to Polydore Vergil, ‘that day he would make end either of war or life’; he would ‘die like a king or win victory in this field.’  He was wounded several times but refused the advice of his few companions to flee.  He also refused the offer of a horse.  His heroism was evident to all.  In the end, he could not prevail.  His crown was knocked from his head; his head was struck so many times that the helmet was beaten into the skull; even after his death, his body continued to be beaten.  Around him lay the bodies of his few companions – Conyers, Brackenbury, Ratcliffe….  There is a legend that his crown landed in a hawthorne bush; true or not, it was soon enough in Henry Tudor’s hands – and not because of any personal bravery on the part of the first Tudor king.

The battle lasted about two hours.  Its outcome – Henry’s triumph – was only made possible by Stanley’s disgraceful betrayal of his king.  Had he waited a few moments longer, Henry may have been personally killed by Richard.  That single action inaugurated the Tudor dynasty – and it was a shameful inauguration.  Whatever his qualities before the battle, his actions immediately afterwards are not endearing.  Richard III, who had fought so heroically and suffered an awful death, continued to be humiliated and abused.  His body was slung naked over a horse, arms and legs hanging over the sides; a halter was tossed around his neck to symbolize his defeat.  In this manner, he was taken to a friary in Leicester where his body lay on view for two days; it was naked from the waist down except for a scant and cheap black cloth.  He was buried at the friary with no ceremony.  The church no longer exists – Henry’s son ordered the dissolution of the monasteries in the 1530s and Richard’s grave was opened and the body thrown out.  Later, the coffin was supposedly used as a horse trough and cellar steps in a nearby manor.  Richard III remains the only English king since 1066 to have no burial place.  He was also the last English king to die in battle.

Henry Tudor had now declared himself Henry VII and Lord Stanley placed Richard’s crown upon his stepson’s head.  His officers were busy settling old scores, executing old foes and rounding up the prisoners.  In the end, we can reasonably estimate that about 400 men – in total – died that day.  Of course, after the battle few wanted to talk about the actual fighting – those two hours which ended in betrayal and death for one king and the beginning of one of the most celebrated dynasties in English history.

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