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Jesi has very old origins. The legend says that it was founded by Esio, the king of Pelasgians, whereas it is known that it was a Roman colony since 247 B.C.

With the Barbaric invasions, also the imperial Jesi followed the same fate of other flourishing Roman cities, until the Byzantines drove the Ostrogoths out of Italy in 554 A.D. and included Jesi in the Pentapolis, one of the seven military districts of the Exarchate of Italy.

After the Exarchate of Italy broke up, Jesi was conquered and destroyed by the Lombards, and when the Lombards were driven out by the Franks, their King Pepin the Short ceded Jesi to the papacy in 756 A.D. Since the 8th century the Benedictine monks built a large number of abbeys in the valley of the Esino river, while the papal tyranny fuelled bloody revolts. In 1130 Jesi declared itself a "free commune" (a city-state in medieval Italy), with its own government and statues, sanctioning the end of the feudal era and the beginning of the golden age of the "Respubblica Aesina", when Jesi dominated the territories and castles of the valley with the favour of the Emperor Frederick II, born in the heart of the town on the 26th of December, 1194.

In 1261 the territory under the authority and the jurisdiction of Jesi was at its maximum extent, clashing with the interests of the nearby and powerful city of Ancona. From the second half of the 14th century to early 15th century, the crisis of the republican institutions and the fight for the hegemony among the most important noble families opened up the so-called "Age of the Signorie", i.e. governments run by a lord (signore), which contended for the town of Jesi: first the Malatesta family of Rimini, then Braccio da Montone of Perugia and finally Francesco Sforza, Duke of Milan, who returned Jesi to the papacy in 1447.

Towards the end of the 15th century the town of Jesi revived and grew from the economic and cultural point of view: new buildings were erected, the defence system was reinforced, the first editions of the "Divine Comedy" were printed in 1472 by the typographer from Verona Federico de Conti, and some masterpieces were painted by the Venetian Lorenzo Lotto in the first half of the 16th century. 

The town oligarchy, which had become the ruling class, was able to keep some administrative autonomy from the central power of the Pope, and maintained the power until the end of the 18th century, when the Napoleonic troops arrived in 1797 and stopped both the monopoly that aristocrats held over the town institutions and the control they had over the countryside around Jesi. The 18th century was full of great changes in architecture and urban design altering the face of the town, which expanded beyond the old walls. For Jesi this was also the century of music. Giovan Battista Pergolesi was born there in 1710, whereas Gaspare Spontini was born in 1774 in the neighbouring village of Maiolati. In 1808, with the annexation of the Marche region to Napoleon's Reign, Jesi became one of the capitals of the Department of Metauro and a gradual process of industrialisation started in the town. The Risorgimento events, which would lead to the Italian unification, involved several personalities from Jesi, among which Antonio Colocci.

On the 15th of September 1860, the bersaglieri entered Jesi, whereas five days later, in the neighbouring town of Castelfidardo, the Piedmontese troops defeated the papal army. Jesi became thus part of the Reign of Italy.