Matthias originally intended him for the Church, but on losing all hope of offspring from his queen, Beatrice of Naples, determined, towards the end of his life, to make the youth his successor on the throne.

He publicly declared him his successor, created him a prince with vast apanages in Silesia (Duchy of Głogów) made the commandants of all the fortresses in the kingdom take an oath of allegiance to him, and tried to arrange a marriage for him with Bianca Maria Sforza of Milan, a project which was frustrated by the intrigues of Queen Beatrice.

He was then persuaded to retire southwards with the royal treasures which Matthias had confided to him, whereupon an army immediately started in pursuit, scattered his forces in the battle of Bonefield[2] (July 4, 1490, near Kölesd in Tolna county), and robbed him of everything.

On the invasion of Hungary by Maximilian, he showed his loyalty to the crown by relinquishing into the hands of Vladislaus the three important fortresses in Pressburg (present day Bratislava in Slovakia), Komárom and Tata, which had been entrusted to him by his father.

From 1499 to 1502 he successfully defended the unconquered parts of Bosnia against the Turks, and in the following year aspired to the dignity of Palatine, but was defeated by a combination of Queen Beatrice and his other enemies.