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==Early life== {{Unreferenced section|date=December 2021}} [[File:Margaret of York.png|thumb|Young Margaret of York in a drawing by Jacques de Boucq (1520-1573) taken from a contemporary portrait.]] [[Isabella of Portugal, Duchess of Burgundy|Duchess Isabella of Burgundy]], the mother of [[Charles the Bold]], was, through her blood ties and her perception of Burgundian interests, pro-English. As a granddaughter of [[John of Gaunt]], she was consequently sympathetic to the [[House of Lancaster]]. She believed that Burgundian trade, from which the Burgundian State drew its vast wealth, depended upon friendly relations with England. For this reason she was prepared to favour any English faction which was willing to favour Burgundy. By 1454, she favoured the [[House of York]], headed by Margaret's father, [[Richard of York, 3rd Duke of York|Richard, 3rd Duke of York]]. Although the King of England, [[Henry VI of England|Henry VI]], was the head of the House of Lancaster, his wife, [[Margaret of Anjou]], was a niece of [[Burgundian State|Burgundy]]'s bitter enemy, [[Charles VII of France]], and was herself an enemy of the Burgundians. The Duke of York, by contrast, shared Burgundy's enmity towards the French, and preferred the Burgundians. Because of this, when the Duke of York came to power in 1453β1454, during Henry VI's first period of insanity, negotiations were made between himself and Isabella for a marriage between Charles the Bold, then [[Count of Charolais]], and one of York's unmarried daughters, of whom the 8-year-old Margaret was the youngest. The negotiations petered out, however, due to power struggles in England, and the preference of Charles's father, [[Philip the Good]], for a French alliance. Philip had Charles betrothed to [[Isabella of Bourbon]], the daughter of [[Charles I, Duke of Bourbon]], and [[Agnes of Burgundy, Duchess of Bourbon|Agnes of Burgundy]], in late March 1454, and the pair were married on 31 October 1454. Margaret, being a useful bargaining tool to her family, was still unmarried at age 19, when [[Isabella of Bourbon]] died in September 1465. She had borne Charles only a daughter, [[Mary of Burgundy|Mary]], which made it an imperative for him to remarry and father a son. The situation had changed since 1454: Charles was now highly respected by his father, who had in his old age entrusted the rule of Burgundy to his son. Charles was pro-English, and wished to make an English marriage and alliance against the French. For her own part, Margaret's family were far more powerful and secure than they had been in 1454: her father had been killed at the [[Battle of Wakefield]] on 30 December 1460, but her brother was now King [[Edward IV of England|Edward IV]], opposed ineffectively only by Margaret of Anjou and her son, [[Edward of Westminster]]. This made Margaret a far more valuable bride than she had been as the mere daughter of a duke. Because of this, Charles sent his close advisor, Guillaume de Clugny, to London weeks after the death of his wife, to propose to Edward IV a marriage between himself and Margaret. Edward responded warmly, and in spring 1466 sent his brother-in-law, [[Anthony Woodville, 2nd Earl Rivers|Lord Scales]], to Burgundy, where Scales made a formal offer of Margaret's hand in marriage to Charles, and put forward Edward's own proposal of a reciprocal marriage between Charles' daughter Mary and Edward's brother, [[George Plantagenet, 1st Duke of Clarence|George, 1st Duke of Clarence]].
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