Vlad II Dracul

Born illegitimate to Mircea I of Wallachia before 1395, Vlad spent his youth at Sigismund of Luxembourg's court, joining the Order of the Dragon in 1431 and earning recognition as Wallachia's lawful voivode - though his half-brother Alexander I Aldea held the throne until 1436. With Hungarian support Vlad took power that year, but after Sigismund died in 1437 he shifted allegiance to Ottoman Sultan Murad II, even joining Murad's 1438 invasion of Transylvania. When he flirted with a crusade in 1441, the sultan summoned him to Edirne and took him prisoner in 1442, forcing Vlad to leave his two young sons - future players in the region's brutal politics - as hostages. Restored by the Ottomans in 1443, he played both sides: neutral during Hunyadi's Long Campaign, then sending 4,000 horsemen to the Crusade of Varna and capturing the fortress at Giurgiu in 1445. A peace with the Ottomans in 1446 or 1447 broke his relationship with Hunyadi, who invaded Wallachia in late November 1447 and drove Vlad from Târgoviște, where he was killed in a nearby village.