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Archduchess Joanna of Austria, Charlotte des Essarts, Francesco I de' Medici, Grand Duke of Tuscany, Henriette d'Entragues, Jacqueline de Bueil, King Felipe I of Castile, King Henri IV of France and Navarre, Marie de Medici of Florence, Queen Joanna of Castile, Queen of France and Navarre
By early 1599, Henri’s marriage to Margaret of Valois looked likely to be annulled at last. And so, at the age of forty-six and still without a legitimate heir, Henri felt free to propose to Gabrielle d’Estrées. On Mardi Gras, Henri placed on her finger the ring with which he had “married” France at his coronation in 1593.
During Holy Week, however, Gabrielle, who was pregnant at the time, fell ill; by Holy Saturday, to the relief of many in France, she was dead. Rumours flew that she had been poisoned, but in fact she died from eclampsia and a premature birth of a stillborn son.
Though grief-stricken, Henri grasped that his fiancée’s death had saved him from disaster: his plan to declare his two sons by d’Estrées heirs to the throne would have precipitated a major political crisis.

Henri IV, King of France and Navarre
Henri provided Gabrielle d’Estrées with a grandiose funeral and drowned his sorrows with a sustained spree of womanising. Sir Henry Neville, the English ambassador, reported that Henry was spending time “in secret manner at Zamet’s house”, where “la belle garce Claude” was known to entertain, and that he was fervently courting Henriette d’Entragues, the daughter of Charles IX’s former mistress, Marie Touchet.
Royal accounts record that Henri was soon making large payments to “Mademoiselle d’Entragues”, as well as to “Mademoiselle des Fossez”. D’Entragues quickly replaced d’Estrées as Henry’s principal mistress.
She extracted from him, in Neville’s words, “100,000 crowns in ready money and an yearly pension” as proof of his commitment. At about the same time, Henri began affairs with Marie Babou de la Bourdaisière and with two wives of Paris parlement members, madames Quélin and Potier.
Marie de’ Medici
In October 1599, the parlement of Paris officially petitioned that Henri marry a princess worthy of his dignity. Henri took note and began considering candidates from several foreign states. According to Sully, however, he ruled out a German wife, on the grounds that it would feel like going to bed with a wine-barrel.
Henri IV was keenest on Maria de’ Medici of Florence, the niece of Ferdinando I de’ Medici, Grand Duke of Tuscany.
Maria was the sixth daughter of Francesco I de’ Medici, Grand Duke of Tuscany, and Archduchess Joanna of Austria, the youngest daughter of Ferdinand I, Holy Roman Emperor and Anna of Bohemia and Hungary.
She was a descendant of Lorenzo the Elder –a branch of the Medici family sometimes referred to as the ‘cadet’ branch– through his daughter Lucrezia de’ Medici, and was also a Habsburg through her mother, who was a direct descendant of Queen Joanna of Castile and King Felipe I of Castile.
Although Maria’s ancestry was impressive, what Henri found particularly attractive about Maria was her enormous wealth.
On December 17, 1599, the Archbishop of Arles pronounced the annulment of Henri’s marriage to Margaret of Valois. The Medici marriage contract was signed in April 1600, pledging a huge dowry of 600,000 écus, part of which was subtracted to pay Henry’s debts to Ferdinando.
Henri played his part by proclaiming undying devotion to Maria in a series of letters, though he was sending similar love letters to Henriette d’Entragues, telling her in one that he wanted to kiss her a million times.

Young Marie de’ Medici of Florence
A proxy marriage took place in Florence in October 1600, and then Maria—to be known in France as Marie—sailed in great pomp for Marseille, where she disembarked on November 3. Marie was 26 and King Henri was 47 at the time of thier marriage.
Henri on campaign in Savoy, rode to meet her at Lyon, where he found her at supper. He visited her afterwards in her chamber; according to Ralph Winwood, secretary to English ambassador Sir Henry Neville:
She met him at the door, and offered to kneel down, but he took her in his arms, where he held her embraced a long time … He doth profess to the World the great Contentment he finds in her, how that for her Beauty, her sweet and pleasing carriage, her gracious behaviour, she doth surpass the relation which hath been made of her, and the Expectation which he thereby conceived.
The couple underwent a second marriage ceremony in Lyon; and Marie finally reached Paris on February 7, already pregnant. She found her new home, the Louvre, so shabby that at first she thought Henri was playing a joke.
She gave birth to a son, Louis, at the Palace of Fontainebleau on September 27, 1601, to the delight of Henri IV, who had rushed from military duties to her bedside to serve, he joked, as one of her midwives. The moment Henri was told that the child was a boy, he ushered two hundred courtiers into the chamber to share the euphoria.
The baby was fed a spoonful of wine and handed over to a governess, Baroness Robert de Harlay, baron de Monglat [fr], and to the physician Jean Héroard [fr], an expert on the bone structure of horses. According to Winwood, the baby was a “strong and a goodly prince, and doth promise long life”. The birth of a dauphin, as the first son of a French king was known, inspired rejoicing and bonfires throughout France.
Marie believed that after bearing a son, she “would begin to be a Queen ueen”. However, a few weeks later, Henriette d’Entragues also produced another son (Gaston Henri, Duc de Verneuil) and Henri not only made just as much fuss over this son but declared that he was better-looking, not fat and dark like Louis and the Medici.
In the words of biographer David Buisseret, “the royal couple was well embarked upon nine years of mutual recrimination and misunderstandings, in which the fault plainly lay with the king”.

Marie de’ Medici, Queen of France and Navarre
Henri had made Marie’s position clear to her from the first. When she began by pressing him to accept the decrees of the Council of Trent, he told her to keep her nose out of state business and look after herself. Shortly after Marie’s arrival in Paris, Henri had introduced Henriette d’Entragues to her, reportedly pushing Henriette further towards the ground when her curtsey was not low enough.
He housed his senior mistress close to the Louvre and was seen dining with the queen and d’Entragues together. Marie also had to cope with a second public mistress, La Bourdaisière, as well as with Henry’s continued visits to Zamet’s house for services provided by “la belle garce Claude”.
In the next nine years, Marie bore Henri six children; but he also sired five more by d’Entragues, Jacqueline de Bueil, and Charlotte des Essarts. Nonetheless, Henri often wrote affectionate letters to Marie and in other ways treated her with respect.