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Emperor Maximilian was married three times, but only the first marriage produced offspring.

Maximilian I (March 22, 1459 — January 12, 1519) was King of the Romans from 1486 and Holy Roman Emperor from 1508 until his death. He was never crowned by the Pope, as the journey to Rome was blocked by the Venetians. He proclaimed himself elected emperor in 1508 (Pope Julius II later recognized this) at Trent, thus breaking the long tradition of requiring a papal coronation for the adoption of the Imperial title. Maximilian was the only surviving son of Friedrich III, Holy Roman Emperor, and Infanta Eleanor of Portugal. Since his coronation as King of the Romans in 1486, he ran a double government, (with a separate court), with his father until Friedrich III’s death in 1493.

Maximilian I, Holy Roman Emperor

Maximilian’s first wife was Mary of Burgundy (1457–1482).

Mary (February 13, 1457 – March 27, 1482), nicknamed the Rich, was a member of the House of Valois-Burgundy who ruled a collection of states that included the duchies of Limburg, Brabant, Luxembourg, the counties of Namur, Holland, Hainaut and other territories, from 1477 until her death in 1482.

As the only child of Charles I the Bold, Duke of Burgundy, and his wife Isabella of Bourbon, a daughter of Charles I, Duke of Bourbon and Agnes of Burgundy, Mary inherited the Burgundian lands at the age of 19 upon the death of her father in the Battle of Nancy on January 5, 1477. In order to counter the appetite of the French king Louis XI for her lands, she married Archduke Maximilian of Austria.

They were married in Ghent on August 19, 1477, and the marriage was ended by Mary’s death in a riding accident in 1482. Mary was the love of his life. Even in old age, the mere mention of her name moved him to tears (although, his sexual life, contrary to his chivalric ideals, was unchaste).

Mary of Burgundy

The grand literary projects commissioned and composed in large part by Maximilian many years after her death were in part tributes to their love, especially Theuerdank, in which the hero saved the damsel in distress like he had saved her inheritance in real life.

Beyond her beauty, the inheritance and the glory she brought, Mary corresponded to Maximilian’s ideal of a woman: the spirited grand “Dame” who could stand next to him as sovereigns. To their daughter Margaret, he described Mary: from her eyes shone the power (Kraft) that surpassed any other woman.

The marriage produced three children:

1. Philipp of Burgundy (1478–1506) who inherited his mother’s domains following her death, but predeceased his father. He married Joanna of Castile, becoming king-consort of Castile upon her accession in 1504, ruled Castile via the concept Jure uxoris (a Latin phrase meaning “by right of (his) wife”) and is known as King Felipe I of Castile. He and was the father of the Holy Roman Emperors Charles V and Ferdinand I.

The meeting of Maximilian and Mary of Burgundy

2. Margaret of Austria (1480–1530), who was first engaged at the age of 2 to the French dauphin (who became Charles VIII of France a year later) to confirm peace between France and Burgundy. She was sent back to her father in 1492 after Charles repudiated their betrothal to marry Anne of Brittany. She was then married to the crown prince of Castile and Aragon Juan, Prince of Asturias, and after his death to Philibert II of Savoy, after which she undertook the guardianship of her deceased brother Philipp’s children, and governed Burgundy for the heir, Charles.

3. Francis of Austria, who died shortly after his birth in 1481.

Maximilian’s second wife was Anne of Brittany (1477–1514) the eldest child of Duke Francis II of Brittany and his second wife Margaret of Foix, Infanta of Navarre.

Anne of Brittany

They were married by proxy in Rennes on December 18, 1490, but the contract was dissolved by Pope Alexander VI in early 1492, by which time Anne had already been forced by the French king, Charles VIII (the fiancé of Maximilian’s daughter Margaret of Austria) to repudiate the contract and marry him instead.

The drive behind this marriage, to the great annoyance of Maximilian’s father, Emperor Friedrich III (who characterized it as “disgraceful”), was the desire of personal revenge against the French (Maximilian blamed France for the great tragedies of his life up to and including Mary of Burgundy’s death, political upheavals that followed, troubles in the relationship with his son and later, Philipp’s death ).

Maximilian, as the young King of the Romans, had in mind a pincer grip against the Kingdom of France, while Friedrich III wanted him to focus on expansion towards the East and maintenance of stability in newly reacquired Austria. But Brittany was so weak that it could not resist French advance by itself even briefly like the Burgundian State had done, while Maximilian could not even personally come to Brittany to consummate the marriage.

Maximilian’s third wife was Bianca Maria Sforza (1472–1510). She was the eldest legitimate daughter of Duke Galeazzo Maria Sforza of Milan by his second wife, Bona of Savoy, daughter of Louis, Duke of Savoy and Anne de Lusignan of Cyprus.

Bianca Maria Sforza

They were married in 1493, the marriage bringing Maximilian a rich dowry and allowing him to assert his rights as imperial overlord of Milan. The marriage was unhappy, and they had no children. In Maximilian’s view, while Bianca might surpass his first wife Mary in physical beauty, she was just a “child” with “a mediocre mind”, who could neither make decisions nor be presented as a respectable lady to the society.

Benecke opines that this seems unfair, as while Bianca was always concerned with trivial, private matters (Recent research though indicates that Bianca was an educated woman who was politically active), she was never given the chance to develop politically, unlike the other women in Maximilian’s family including Margaret of Austria or Catherine of Saxony.

Despite her unsuitability as an empress, Maximilian tends to be criticized for treating her with coldness and neglect, which after 1500 only became worse. Bianca, on the other hand, loved the emperor deeply and always tried to win his heart with heartfelt letters, expensive jewels and allusions to sickness, but did not even get back a letter, developed eating disorders and mental illness, and died a childless woman.

Joseph Grünpeck, the court historian and physician, criticized the emperor, who, in Grünpeck’s opinion, was responsible for Bianca’s death through neglect.

In addition, he had several illegitimate children, but the number and identities of those are a matter of great debate. Johann Jakob Fugger writes in Ehrenspiegel (Mirror of Honour) that the emperor began fathering illegitimate children after becoming a widower, and there were eight children in total, four boys and four girls.