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Charles VIII, called the Affable (June 30, 1470 – April 7, 1498), was King of France from 1483 to his death in 1498. He was the eldest son of King Louis XI of France and his second wife Charlotte of Savoy daughter of Louis, Duke of Savoy and Anne of Cyprus. Her maternal grandparents were Janus of Cyprus and Charlotte de Bourbon-La Marche. Her maternal grandmother, for whom she was probably named, was a daughter of Jean I, Count of La Marche, and Catherine de Vendôme. She was one of 19 children, 14 of whom survived infancy.

Charles VIII, King of France

Prince Charles succeeded his father Louis XI at the age of 13. His elder sister Anne acted as regent jointly with her husband Peter II, Duke of Bourbon until 1491 when the young king turned 21 years of age. During Anne’s regency, the great lords rebelled against royal centralisation efforts in a conflict known as the Mad War (1485–1488), which resulted in a victory for the royal government.

Charles was betrothed on July 22, 1483 (a month before he succeeded to the throne) to the 3-year-old Archduchess Margaret of Austria, daughter of the Archduke Maximilian of Austria (later Holy Roman Emperor Maximilian I) and Mary, Duchess of Burgundy. The marriage was arranged by Louis XI, Maximilian, and the Estates of the Low Countries as part of the 1482 Peace of Arras between France and the Duchy of Burgundy. Archduchess Margaret brought the counties of Artois and Burgundy to France as her dowry, and she was raised in the French court as a prospective queen.

In 1488, however, François II, Duke of Brittany, died in a riding accident, leaving his 11-year-old daughter Anne his daughter by his second wife Margaret of Foix, Infanta of Navarre, as his heir. Anne, who feared for the independence of her duchy against the ambitions of France, arranged a marriage in 1490 between herself and the widower Archduke Maximilian.

Anne of Brittany, Queen Consort of France

The regent Anne of France and her husband Peter refused to countenance such a marriage, however, since it would place Maximilian and his family, the Habsburgs, on two French borders. The French army invaded Brittany, taking advantage of the preoccupation of Maximilian and his father, Emperor Friedrich III, with the disputed succession to Mathias Corvinus, King of Hungary. Anne of Brittany was forced to renounce Maximilian, whom she had only married by proxy in a ceremony of questionable validity and agreed to be married to Charles VIII instead.

Preoccupied by the problematic succession in the Kingdom of Hungary, Maximilian failed to press his claim. Upon his marriage, Charles became administrator of Brittany and established a personal union that enabled France to avoid total encirclement by Habsburg territories.

The official marriage between Anne and King Charles VIII of France was celebrated in the Great Hall of the Château de Langeais on December 6, 1491 at dawn. The ceremony was concluded discreetly and urgently because it was technically illegal until Pope Innocent VIII, in exchange for substantial concessions, validated the union on February 15, 1492, by granting the annulment of the marriage by proxy with Maximilian, and also giving a dispensation for the marriage with Charles VIII, needed because the King and Anne were related in the forbidden fourth degree of consanguinity.

To secure his rights to the Neapolitan throne that René of Anjou had left to his father, Charles made a series of concessions to neighbouring monarchs and conquered the Italian peninsula without much opposition. A coalition formed against the French invasion of 1494–98 finally drove out Charles’ army, but Italian Wars would dominate Western European politics for over 50 years.

Charles died on April 4, 1498 after accidentally striking his head on the lintel of a door at the Château d’Amboise, his place of birth. Since he had no male heir, he was succeeded by his cousin Louis XII from the Orléans cadet branch of the House of Valois. Louis XII the son of Charles, Duke of Orléans, and Maria of Cleves, and cousin Charles VIII.

Louis XII, King of France

When Charles VIII, Anne of Brittany was 21 years old and without surviving children. Three days after her husband’s death, the terms of her marriage contract came into force; however, the new King, Louis XII, was already married, to his cousin Jeanne, daughter of Louis XI and sister to Charles VIII. On August 19, 1498, at Étampes, Anne agreed to marry Louis XII if he obtained an annulment from Joan within a year. Days later, the process for the annulment of the marriage between Louis XII and Joan of France began. In the interim, Anne returned to Brittany in October 1498.

The initial marriage contract with Charles VIII provided that the spouse who outlived the other would retain possession of Brittany; however, it also stipulated that if Charles VIII died without male heirs, Anne would marry his successor, thus ensuring the French kings a second chance to annex Brittany permanently.

If Anne was gambling that the annulment would be denied, she lost: Louis’s first marriage was dissolved by Pope Alexander VI before the end of the year. Anne’s third marriage contract, signed the day of her marriage (Nantes, January 7, 1499), was concluded.

Louis XII and Anne of Brittany left only two daughters, the eldest Claude of France (1499-1524), who succeeded her mother as Duchess of Brittany and later also became Queen consort of France as wife of François I, who was the son of Charles, Count of Angoulême, and Louise of Savoy. François I was first cousin once removed from Louis XIII who was also his and father-in-law.