Cortona became a roman colony under Lucius Cornelius Silla. On June 24 217 B.C., during the second Punic war, one of the bloodiest massacres in history took place in the immediate vicinity of the town, on the shores of Lake Trasimeno, where the roman legions led by Consul Flaminius were crushed by Hannibal.
During the barbaric invasions Cortona was razed by the Goths in 450 A.D. and only centuries later, in the 13th century, did the town surface anew in history as a free Commune, minting its own coinage and often in open war with Arezzo. Cortona sided with the Ghibelline faction and was visited by emperors Frederick II of Sweden and Henry VII of Luxembourg who bestowed privileges on the town. In 1325 the Casali family, as a reward of their political merits, were conferred the Seigniory of the town which they held as late as 1409.
In 1529 Cortona followed the fate of the Grand Duchy of Tuscany, first under the Medicis and later, from 1737 on, under the Lorenas, to become eventually, after the 1860 plebiscite, part of the newly-born Kingdom of Italy. Cortona’s buildings, churches and illustrious sons bear testimony to its medieval and renaissance past.