Vlad III Dracula (1431–1476) became Voivode (Prince) of Wallachia for the second time in 1459, ruling from 1456 to 1462, during one of his three reigns over the land previously governed by his father, Vlad II, and grandfather, Mircea. As in his first reign in 1448, Wallachia remained a tributary state of the Ottoman Empire, obligated to pay an annual tribute of 10,000 ducats and provide 500 soldiers. However, the political situation had significantly evolved: Vlad III had eliminated the treacherous boyars (nobles), plundering their castles and using their wealth for Wallachia's benefit. To further consolidate power and keep the Ottomans out of his territory, he allied with his friend King Matthias Corvinus of Hungary, who had been tasked by Pope Pius II to lead a crusade against the Sultan (Council of Mantua, 1459). 

Matthias wanted Vlad at the forefront of the campaign, recognizing him as the most skilled strategist in both understanding and combating the Turks. Meanwhile, Sultan Mehmed II — who had grown up with Vlad and shared a relationship as both friend and rival — sought to persuade Vlad to remain loyal to the Ottomans. Mehmed sent 2 emissaries to Wallachia, urging Vlad to pay the required tribute. However, Vlad III had no intention of submitting. Paying the tribute would symbolize not only his submission but also Wallachia's subjugation to the Sultan. Instead, he had demonstrated his allegiance to Christendom by being the only Christian power at the time to send military aid to Pope Pius II and Matthias Corvinus.

When the 2 Ottoman emissaries arrived at Vlad Dracula's court, he refused to provide the requested money and soldiers. To justify his defiance, he accused the envoys of insulting him. The reason? As Muslims, they had not knelt or removed their hats — a custom Vlad exploited to his advantage. To the Wallachian Voivode, this was a sign of disrespect. In response, Vlad had the envoys executed in a display of brutality: he nailed their hats to their heads, declaring that they would now have a permanent reason never to remove them.

This act marked the beginning of Vlad’s defiance of the Ottoman Empire, solidifying his reputation as a ruthless leader.