Here was someone whose father was dead before he was born to 14-year old Margaret Beaufort, whose royal blood came from the illegitimate scions of Edward III’s son John of Gaunt and his mistress Katheryn Swinford who had been barred from the throne by Henry IV.
Henry’s father Edmund Tudor had been Earl of Richmond, a title granted only because of his own father’s marriage to Katherine of Valois, the French Queen of Henry V. As the half-brothers of Henry VI, Edmund and his brother Jasper were natural-born adherents of the House of Lancaster. However, upon the ascension of Edward IV of York, the wardship of young Henry was given to the Yorkist Herbert family in hopes that he would grow up to be a stalwart Yorkist loyalist. The brief triumph of Lancaster and Edward’s flight into exile changed all that. Jasper took charge of his 14-year old nephew and, with the reclamation of Edward’s throne in 1471, carried Henry away into exile in Brittany, having been forced away from France by a storm at sea.
For the next 12 years, Henry was a political pawn, as Edward IV connived to have him returned to England, Duke Francis of Brittany used him as a bargaining chip, and his mother negotiated for the return of his earldom and his safe return to England. Reaching manhood under such precarious and penurious conditions probably made Henry shrewd, but it likewise made him paranoid and suspicious.
The death of Edward IV and what happened afterwards changed Henry’s fortunes. Upon Edward’s death, Duke Francis allowed Henry more freedom. Upon Edward V’s deposition, Henry became someone worth petitioning, as Yorkist loyalists sought support for Edward’s restoration. Margaret Beaufort’s surreptitious moves in Edward’s favor were undoubtedly motivated by her tireless devotion to her son and probably enhanced her value and that of Henry within Richard’s opposition. When rumors of Edward’s and young Richard of York’s deaths began to circulate in September 11483, she was able to capitalize on her son’s bachelorhood by advancing him as a marriage partner for Elizabeth of York, who was now her father’s heir following her brothers’ deaths.
The fact that Henry was not well known, having been out of England since age 14, probably worked to his benefit, because he could then be painted in the most idealistic of terms. The Croyland Chronicler supports this when he writes that Henry was welcomed like an angel from heaven when he entered London following Richard III’s defeat at Bosworth. This view of Henry, however, was far from accurate.
One of the ways in which people display character is the manner in which they handle success. Henry was given a great opportunity to truly unite the warring roses under his reign and under his marriage to Elizabeth of York, as the Tudor Rose and the poets of the time romantically depicted this union. However, he squandered his opportunity. He could not overcome the suspiciousness bred into him from his dangerous youth, nor could he overcome the realization that he was only, after all, the Yorkist loyalists’ “second-best substitute for Edward IV’s dead sons.” (Christine Carpenter)
And yet, Henry fell all too easily into the kingly mode. As the English rebels escaped Richard III through self-imposed exile and joined Henry in Brittany and, later, France, Henry’s situation more and more resembled a royal court. He began to address his letters as “HR” — Henricus Rex — even before Bosworth, and used the royal “we” in reference to himself. In his letters, he even suggested that Richard was the traitor for denying him his rightful place! When he first landed in Wales after sailing from France, he knelt, kissed the ground, prayed for the success of his cause, and knighted several of his followers, as if he were already King. His letters to would-be supporters, asking them for their assistance against Richard, were a combination of flattery and threats, as he warned them of incurring “our displeasure.” Some might say that these were the actions of a clever man. I wouldn’t doubt that he was clever enough himself to begin a campaign of self-glorification that would eventually lead to the replacement of the kingly address “Your Grace” with the exulted “Your Majesty.”
However, Henry VII might have been one of the most insecure personalities to ever sit on the English throne. Regardless of whatever attempts he might have made to celebrate himself in a role he was not born to play, it seems that he was always compensating for an inner realization that he was only where he was because of fate, not because of merit. His bias in the Wars of the Roses had always been for the House of Lancaster, but, had Lancaster been triumphant, he would have been nothing more than the Earl of Richmond. Likewise, had Edward IV’s heir Edward V succeeded his father in peace, Henry could never have aspired to anything more than Earl of Richmond. It was disappearance and presumed murder of Edward V and Richard, Duke of York, that elevated their sister Elizabeth to the status of Edward IV’s heir, thus giving Henry, a bachelor, an opportunity to aim at something more than an earldom.