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In the early years of his reign, he remained allied with Poland and the Ottoman Empire, and even joined the Ottomans in attacking Wallachia.
He also supported the rebellion of 1467 of the Transylvanian Estates ; therefore Matthias I of Hungary launched an expedition against Moldavia, but the royal army was defeated in the battle of Baia.
He came to view the Ottoman Empire as his chief enemy in the 1470s, and in 1474 he refused to pay tribute.
He soon received the ultimatum of Mehmed II who demanded the surrender of Chilia, a fortress recently captured from Wallachia.
Upon Stephen III's refusal, a large Ottoman army was sent against Moldavia.
He called on Pope Sixtus IV, pleading for a crusade.
Although the pope acknowledged his merits, by naming him " the Athlete of Christ ", no anti-Ottoman coalition materialized.
Even without external military support, Stephen the Great led his troops to victory in the battle of Vaslui on January 10, 1475.
Following the battle, he addressed a letter to the Christian princes, expressing the idea that the two Romanian principalities were the " gateway to the Christian world ", and if they fell " all Christendom would be in danger ".

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