By all means, King Richard III had no reason to be nervous in the battle to come. He was a capable general, successfully fending off Lancastrian rebellions throughout the Wars of the Roses. Time and again he secured the dynasty House of York. It was once again left to him to defend the hold House York had on the throne. He had the more experienced, more numerous forces. Knowing that there was no way he could lose, the War King strode on to battle the morning of the 22 of August 1485 with the confidence that the battle would be easily won.¹ It was his duty alone as the lone surviving York to end this conflict and allow him to reign with uncompromising strength and stability. This sentiment lost the war. The successful kings of the Wars of the Roses were marked by support from their trusted alliances as well as support from Parliament and the people.

By 1399, only two dukedoms had survived of the royal line of Edward III, House Lancaster and House York.² House Lancaster ruled England from the time of Henry IV, who had usurped Richard II in defense of his inheritance of the riches of House Lancaster.³ Lancasters ruled England for the next three generations, when instability began to plague the rule of Henry VI. The Hundred Years’ War ended during Henry’s reign with a French victory and England losing much territory. This made Henry an unpopular ruler. King Henry was seen as soft and weak-willed, giving in to Parliament too easily. The king suffered the first of many mental breaks in 1453, leaving him in a deep depression and unable to rule. At this time, Henry had no heir, leaving his throne vulnerable to a coup. His incapacitation led many members of Parliament to lose faith in him despite his loyalty to their advice. Due to his royal lineage and sound mind, many supporters felt Richard, duke of York, would be a better king than Henry. So, the duke of York took advantage of Henry VI’s unpopularity combined with his lack of an heir. When the King was declared incapacitated, the duke of York and the duke of Somerset struggled for the power of the regency. In 1454, Richard of York was named protector of England, imprisoning his rival. But, the king recovered the following year. Enraged, he set the duke of Somerset free and stripped Richard of his dukedom. However, this served to isolate him further from Parliament, especially the Yorkist supporters. The displaced duke of York took to the battlefield at St. Albans soon after, killing Somerset and inciting the War of the Roses, named for the sigils of the two royal houses.⁴

Working to restore stability, the duke of York sought not to overthrow the king, but to instill his family as the heirs to the throne, restoring himself as the protector and heir apparent. He made a key alliance with Richard, the Earl of Warwick, who committed his massive forces and brilliant tactics to the Yorkist cause. This alliance became key to the York victories that followed. Warwick dominated the subsequent battles against Queen Margaret of Anjou, who raised an army to defend the inheritance of her newborn son. She briefly acted as protector in the name of her husband before being pushed out again by the Yorkists. She made her last stand in December 1460, rescuing her husband and fleeing to Scotland. Although at the second battle of St. Albans, the duke of York was killed, his ambitions still lived in the hearts of his sons, Edward, George, and Richard.⁵ Young, courageous, and handsome, it was easy for Edward to gain ground with his allies, proving his prowess on the battlefield. Quickly marching west, he intended to assert his father’s claim to the throne.⁶ Only three months later, Warwick and Edward fought their way to London, where Edward was proclaimed king.

The eldest York proved to be charismatic and popular among the people as King Edward IV, asserting stability in relative peace just as he found victory in war. Warwick was his most loyal and trusted advisor. Edward IV was a worthy administrator, ending conflicts with France and encouraging trade. The increased economic activity allowed him to eliminate or reduce many burdensome taxes. He brought stability and reliability that Henry VI could not provide.⁷ This stability reassured his supporters that they had been right in disposing of Henry VI. However, he made a disastrous mistake by betraying Warwick’s confidence, secretly marrying Elizabeth Woodville, a commoner whose family had supported the Lancasters over a strategic marriage to a French princess. This was the first sign of the diminished influence Warwick had over the king. It was clear that Warwick could not control the young monarch. After Edward rejected marriage alliances between the royal family and Warwick, the Earl turned to support the king’s brother George in his bid for the throne through a marriage to his daughter. Richard remained loyal to Edward IV, while George was dismissed from court. The alliance between Warwick and the Yorks had failed and he turn his efforts for control elsewhere. When the plot to turn brother against brother failed, Warwick allied with Queen Margaret of Anjou to restore the banished king Henry VI to the throne in 1470, earning him the title “the Kingmaker” in English history.⁸ By turning his back on the alliances that his father had carefully crafted, Edward IV had overestimated his power. He lost support of the man that put him on the throne, forgetting that the “Kingmaker” would just as easily take the title away.

Still, Edward was the more popular king, and he was quick to build new alliances, especially with his Woodville in-laws that he elevated in status. Easily acquiring an army, Edward IV retook the Crown, and had Henry VI killed the following May. Warwick had been slain along with Henry’s son in battle defending the Lancastrian throne. For the remaining years of Edward’s reign, England appeared to regain stability. However, he contracted a fever and died, leaving his throne to his twelve-year-old son, appointing Richard, as his regent.⁹ The son Edward V was too young to make political decisions on his own, giving him little chance to gain trust and support among his subjects.

Although Richard was quick to declare his allegiance to the young king, he had the new monarch set up in the Tower of London with his younger brother, which served as both a refuge for kings and a prison. During the summer of 1483, the boys were often seen playing on the Tower’s grounds before they suddenly disappeared. They quickly moved to have the boys declared illegitimate by declaring his brother’s marriage to Elizabeth Woodsville invalid. The young princes were never seen again. It is widely believed that Richard had them killed to set himself up as heir to the throne. These claims are further made likely with the executions of Dowager Queen Elizabeth’s family. By July, he was crowned Richard III.¹⁰ The only rival for the crown left was Henry Tudor.

Henry Tudor was the last heir of House Lancaster. Growing up in Wales, he had spent little time in England. However, unlike Edward IV, the young challenger had never seen battle before Bosworth.¹¹ Before reaching the heart of England, it was hardly believed that he would succeed in leaving Wales. The army that Henry had raised was made up of a band of exiles from France who had little to no experience in military affairs. However, Henry had made powerful alliances that made the risk of invasion worth the price of the Crown.¹² In this respect, Henry Tudor was unlike any other usurper during the War of the Roses.

Henry Tudor was hardly a candidate to inherit the throne. He was the half-nephew of the deposed King Henry VI, his father was the son of the widowed Queen Catherine of Valois and Owen Tudor. Henry himself grew up with friends of House York.¹³ He was being raised by his uncle Jasper at Pembrooke when the castle was delegated to the Yorkist William Herbert, who took control of his education. Herbert intended to raise the Tudor boy to be an advisor to the Yorkist Kings. However, Warwick the Kingmaker defected from the Yorkists and restored Henry VI to the throne. As Edward IV forced his way back to the throne, the remaining heirs of Lancaster dwindled and Henry was whisked away from England by his uncle Jasper, where he would bide his time in Wales before mounting a force to challenge Richard III.¹⁴

Having never seen a battle, Henry relied on his allies to face Richard III. Jaspar Tudor had spent over thirty years fighting the Yorkist usurpers. John de Vere, duke of Oxford proved valuable in Henry’s battle at Bosworth Field. His father had been killed by Edward IV and he had helped in restoring Henry VI in 1470.¹⁵ Henry found an unlikely ally in Edward IV’s widow, Elizabeth Woodville. Out of fear that she would never see her sons again, the Queen Mother began an alliance with Henry Tudor, offering her daughter, Princess Elizabeth of York, in marriage uniting the two great houses.¹⁶ The final piece of strategy was the marriage of Henry’s mother, Margaret Beaufort, to Thomas, Lord Stanley. Although it took her two years to convince him to support her son, the alliance secured Henry’s claim and surrounded him with capable military commanders.¹⁷ Much like Edward IV, Henry came to value critical alliances, and surrounded himself with trusted advisors. He may not have proven himself in war, but he could provide stability in the wake of the chaos surrounding Richard III.

In contrast, much like Henry VI, Richard was an unpopular king. The missing princes from the Tower and the execution of his sister-in-law’s family forced Parliament to question Richard’s morality. As the rumors increased, Henry Tudor gained a more stable claim to the throne. Then in April 1484, Richard’s only son died, leaving no legitimate heir. When Richard’s wife, Queen Anne died of tuberculosis, rumors spread that Richard poisoned her to be free to remarry. Richard III had failed to gain the support of the masses. His series of missteps weakened House York, leaving the remaining members of the house divided, turning on each other.¹⁸ The unstable morality of Richard III parallels the mental instability of Henry IV. Ultimately, it was this distrust of Richard the third that turned the heads of nobles and commoners alike to favor Henry Tudor.

Looking over Ambion Hill, much like the York conquerors before him, Richard’s forces easily overpowered Henry’s. He had the higher ground, attacking from Albain field.¹⁹ Still, the king was paranoid. There was reason to believe that Sir William Stanley and Thomas, Lord Stanley were conspiring against him. Seeing that the Stanleys were still on his side, there was no way to confirm his suspicions. Hoping to act before loyalty was lost, Richard made a direct attack on Henry, hoping to smother the rebellion at its source. This was his mistake. With the king placed at the center of the action, William Stanley seized the opportunity to enclose the king with his own men alongside the Tudor forces.²⁰

The battle was in full force at the center of the action. Richard was surrounded on all sides. His men fought fiercely to protect their king. But, despite their advantage of experience, the men were overwhelmed.²¹ Fighting until his dying breath, the Stanley soldiers killed Richard, concluding the game of thrones and crowning Henry VII the victor.²²

There is only one decisive truth to the Battle of Bosworth Field. It ended the War of the Roses, with the last heir of Lancaster as the victor.²³ All challenges were unworthy to be pitted against the new royal House of Tudor. Henry married the eldest daughter of Edward IV, Elizabeth of York. By uniting the two great houses, the sigil changing to a red and white rose, the period of civil war had ended, and stability was brought to England, crowning the Tudor King Henry VII.²⁴