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In 1389, Ioannina was besieged by John Bua Spata, and only with the aid of an Ottoman army was Esau able to repel the Albanians.Despite the ongoing Ottoman expansion and the conflicts between Turks and Albanians in the vicinity of Ioannina, Esau managed to secure a period of peace for the city, especially following his second marriage to Spata's daughter Irene in .In the aftermath of the Battle of Pelagonia in 1259, much of Epirus was occupied by the Empire of Nicaea, and Ioannina was placed under siege.Soon, however, the Epirote ruler Michael II Komnenos Doukas, aided by his younger son John I Doukas, managed to recover their capital of Arta and relieve Ioannina, evicting the Nicaeans from Epirus.Following Esau's death in 1411, the Ioannites invited the Count palatine of Cephalonia and Zakynthos, Carlo I Tocco, who had already been expanding his domains into Epirus for the last decade, as their new ruler.By 1416 Carlo I Tocco had managed to capture Arta as well, thereby reuniting the core of the old Epirote realm, and received recognition from both the Ottomans and the Byzantine emperor.Ioannina became the summer capital of the Tocco domains, and Carlo I died there in July 1429.
Many wealthy Byzantine families fled there following the sack of Constantinople, and the city experienced great prosperity and considerable autonomy, despite the political turmoils. Between 14 the city was the administrative center of the Pashalik of Yanina.
In 1366/67 Simeon Uroš, having recovered Epirus and Thessaly, appointed his son-in-law Thomas II Preljubović as the new overlord of Ioannina.
Thomas proved a deeply unpopular ruler, but he nonetheless repelled successive attempts by Albanian chieftains including a surprise attack in 1379, whose failure the Ioannites attributed to intervention by their patron saint, Michael.
After Thomas' murder in 1384, the citizens of Ioannina offered their city to Esau de' Buondelmonti, who married Thomas' widow, Maria.
Esau recalled those exiled under Thomas and restored the properties confiscated by him.