François Valois was the fourth son of Henri II of France (1519-59) and Catherine de' Medici (1519-84). The title duc d'Alençon was bestowed upon him in 1566 by his mother during her regency to his brother Charles IX (1560-74), and was followed by the title duc d'Anjou in 1576.
When d'Alençon was about eighteen he was proposed as a suitable husband for Elizabeth I. The political advantages for such a marriage were firstly to prevent the ascendancy of the English Protestant faction led by Robert Dudley, Earl of Leicester, which might also have stirred up treason among his rivals; and secondly to forge a mutually beneficial alliance with France, which during the Wars of Religion was less hostile to English Protestantism than Spain. D'Alençon himself was also known to have held sympathies for the Huguenots. Although he had been a theoretical candidate for Elizabeth's hand since he was a child, it was not until 1572 that the French Ambassador brought a flattering portrait of the Duke (probably by one of the Dumonstier family) to Elizabeth I, and his courtship started to receive serious consideration.
However, the Queen had heard rumours of the Duke's facial disfigurement ('l'inconvénient du visage') following his contraction of smallpox the year before and refused to make a decision. A further portrait was requested, this time a life-like resemblance. Such was Elizabeth's suspicion that the portrait had to be verified in France by an English envoy and secured in a wooden case with a wax seal before transportation. After the Massacre of St. Bartholomew in August 1572 when some 6,000 French Protestants were murdered, the proposal faltered. But the need for an ally was pressing, and in 1576 a further envoy was dispatched to France to declare that the 'difficultés sur l'aspect du visage' had been overcome and to invite the Duke to the English court. He arrived, full of hope, in the Summer of 1581. This was by far the most serious foreign courtship of Elizabeth's reign. Soon after he arrived she announced to her courtiers that she would marry him, kissed him in public and gave him a ring, but she soon became disenchanted, calling him 'Little Frog'. She continued to be indecisive, and at one Council meeting broke down and wept when the subject of D'Alençon's suit was raised. She was by now in her late forties and the proposed marriage did not have the backing of the whole country. Eventually she decided against him and her cruel remarks drove the disappointed Duke home. D'Alençon was her last political courtship, and by the time he returned to France after ten years acting as her suitor, it was clear that Elizabeth would never marry.
The Order of St. Michael, here worn hanging from a long chain of pearls, was the oldest French Royal Order, created by Louis XI in 1469. It was, however, superceded on 31st December 1578 when the Duke's brother Henri III created the Ordre du Saint-Esprit, thus providing a terminus ante quem for the present portrait.
The facial features of the sitter are highly comparable to two portraits: a bust-length drawing of circa 1572, by Pierre Dumonstier (Bibliothèque Nationale, Paris; see J. Adhémar, "Les portraits dessins du XVIe siècle au Cabinet des Estampes", in Gazette des Beaux-Arts, Sept. 1973), and a full-length by Clouet, dated 1572, aged 18 (ex-Kress collection, Washington), in which his features are slightly softened and he wears the Order of St. Michael with the same single drop-pearl, but suspended from a jewelled chain. In both portraits the Duke appears slightly younger and it may therefore be safe to suggest the present portrait dates from after 1572, but before the creation of the Ordre du Saint-Esprit in 1578.
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