Margaret of Austria was twenty-five and already twice widowed. A king wanted to marry her, and her family was prepared to arrange it. The difficulty was getting her to agree.

The portrait made for that proposed marriage bears the date 29 October 1505. Henry VII had been widowed himself when Elizabeth of York died in 1503, and Margaret, daughter of the Habsburg ruler Maximilian and widow of the Duke of Savoy, was a prestigious possible bride. Her father's agent, Herman Rinck, ordered the picture. There was an English crown on offer. There was also the prospect of another journey to become another man's wife, little more than a year after the last had died.

Margaret had been part of marriage negotiations almost as long as she had been alive. Her mother was Mary of Burgundy, whose inheritance had brought the wealthy Low Countries into the Habsburg family. As a small child Margaret was sent to France to be brought up as the future wife of Charles, the heir to the French throne. He eventually married Anne of Brittany instead. Margaret returned to the Netherlands in 1493, a princess whose intended husband had found a more useful bride.

The next match took her to Spain. In 1497 she married John, the son of Ferdinand of Aragon and Isabella of Castile, heir to both their kingdoms. Her brother Philip married John's sister Joanna, binding the families together in both directions. Margaret was seventeen, with the prospect of becoming a queen ahead of her. John died after roughly six months of marriage. She was pregnant when he died, but their child was stillborn. The alliance had joined two dynasties. Within months, Margaret had lost both her husband and their baby.

In 1501 she married Philibert, Duke of Savoy. His lands lay across strategically important Alpine routes, so this marriage, too, had its uses to her family. It also gave Margaret a place in government: she exercised substantial political influence in the duchy during their marriage. Then Philibert died in 1504. They had been married for three years. She was twenty-four. The next year's negotiations for an English marriage concerned a woman who had already crossed Europe for one husband, married another, and survived them both.

Now her family was arranging a third.

Henry's proposal offered rank, an alliance and a new household in England. Margaret brought her Habsburg connections and the income settled on her through her two previous marriages. Those widow's revenues were supposed to support the woman who had survived. In the English negotiations, they became part of what a new husband stood to receive. Even her bereavements had acquired a financial value that could be written into the next agreement.

In 1506 the arrangements took detailed shape in a contract between Henry and her brother Philip. The dowry was set at 300,000 crowns, with the first 100,000 due within fifteen days of her departure for England. Annual payments connected with her Spanish and Savoyard widowhoods were assigned for Henry's use. Her voyage was provided for, and the marriage ceremony was to follow within a month of her arrival. The negotiators had worked their way through the money and the journey to the wedding.

They still had to obtain the bride's agreement.

Among the provisions was Philip's obligation to persuade his sister to marry. Another placed the same obligation on Maximilian. Her brother could undertake to provide money. Her father could authorise negotiations. Neither undertaking supplied Margaret's consent. The men arranging her future had left themselves a considerable piece of unfinished business, and had written down whose job it was to finish it.

Margaret refused the marriage. The English arrangements did not become an English wedding, and she never married again. Refusing a husband did not mean refusing her family, and it did not take her out of its affairs. There was work ahead for a Habsburg daughter who remained a widow, and it would require rather more of her than standing beside a king.

Philip died in 1506. In 1507 Maximilian appointed Margaret governor of the Netherlands, and with the office came the upbringing of the children Philip had left there, among them a seven-year-old boy who would become the Emperor Charles V. She made her home at Mechelen. The family that had tried to persuade her into an English marriage now entrusted her with its government and its next generation. She brought her Savoyard experience to the work of governing provinces, representing the dynasty and conducting its diplomacy. Remaining unmarried had left her thoroughly occupied.

Henry's portrait, probably this very panel, stayed with her. An inventory of her palace at Mechelen in 1516 recorded it with a cover painted red, and it remained in her collection until her death in 1530. Henry had died in 1509, still a widower. Margaret died a widow, a quarter of a century after the picture was painted. She had kept the king's likeness all that time. She had never agreed to the king.