When Maximilian was three his father tried to arrange a marriage between him and Mary Tudor, the younger daughter of King Henry VII of England.[2] However, Henry VII rejected the proposal citing Mary's young age as the issue.[2]
He was installed as a ruler of Milan in 1512 after the capture of Milan by the Holy League, supported by a Swiss militia led by Jakob Meyer zum Hasen.[3] He ruled from 1512 to 1515,[4] between the occupations of Louis XII of France (1500–1512), and Francis I of France in 1515. Francis I claimed the title of Duke of Milan, as he was descended from Louis I of Orléans and Valentine Visconti who were his great-grandparents. His claims were twofold because he married Claude, the daughter of Louis XII, who was also the great-granddaughter of Louis of Orléans and Valentine.
After the French victory at the Battle of Marignano the arrival of the Venetians, under the command of Bartolomeo d'Alviano, transformed these indecisive battles into a terrible defeat for Matthew Schiner and his Swiss troops who lost 14,000 men. The survivors returned home to Switzerland, taking along the Duke's young brother, Francesco II Sforza, who went to reside in Innsbruck under the guard of Emperor Maximilian I.
The French entered Milan on 17 September 1515 and Maximilian surrendered 17 days later on 4 October. Francis I entered his new duchy on 11 October, accompanied by Charles III of Savoy and William IX of Montferrat who had pledged allegiance to him. The capitulation was complete and Maximilian was imprisoned by the returning French troops.[5] and exiled to France with an annual annuity of 35,000 écus.