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After Thomas' murder in 1384, the citizens of Ioannina offered their city to Esau de' Buondelmonti, who married Thomas' widow, Maria.
On this occasion, Emperor Andronikos II Palaiologos elevated the city to a metropolitan bishopric, and in 1319 issued a chrysobull conceding wide-ranging autonomy and various privileges and exemptions on its inhabitants.
It became part of the Despotate of Epirus following the Fourth Crusade.
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.
The identification of the site with one of the ancient cities of Epirus has not yet been possible. Tsoures dated the Byzantine city walls and the northeastern citadel of the Ioannina Castle to the 10th century, with additions in the late 11th century, including the south-eastern citadel, traditionally ascribed to the short-lived occupation of the city by the Normans under the leadership of Bohemond of Taranto in 1082.
In the treaty of partition of the Byzantine lands after the Fourth Crusade, Ioannina was promised to the Venetians, but in the event, it became part of the new state of Epirus, founded by Michael I Komnenos Doukas.In the period between the 18th and 19th centuries, the city was a major center of the modern Greek Enlightenment.