Although Maximilian was married three times, only the first marriage resulted in children

Although Maximilian was married three times, only the first marriage resulted in children. Mary of Burgundy (1457-1482) was Maximilian's first spouse. The marriage was annulled by Mary's passing in a riding accident in 1482 after they were wed in Ghent on August 19, 1477. His true passion in life was Mary. Even at his advanced age, the simple mention of her name made him cry (although, his sexual life, contrary to his chivalric ideals, was unchaste).

Theuerdank, in particular, in which the hero saved the damsel in peril as if he had preserved her inheritance in real life, was one of the big literary projects that Maximilian commissioned and completed in significant part many years after she passed away. His wish is that her mausoleum in Bruges contains his heart. In addition to her beauty, her inheritance, and the fame she brought, Mary fit Maximilian's ideal of a woman: a vivacious magnificent "Dame" who could coexist with him as sovereign. He gave this description of Mary to their daughter Margaret: "From her eyes shined the force (Kraft) that exceeded any other lady."

The contract between Anne of Brittany (1477-1514) and Maximilian was dissolved by the pope in early 1492, but by that time Anne had already been coerced by the French king Charles VIII (who was engaged to Margaret of Austria) to repudiate the contract and marry him instead. Anne and Maximilian were married by proxy in Rennes on December 18, 1490. In 1493, Maximilian married Bianca Maria Sforza (1472-1510), who brought him a substantial dowry and enabled him to exercise his authority as Milan's imperial overlord. They had no children, and the marriage was unpleasant.