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On 4 June 1502 the city of Arezzo rebelled against Florentine rule, maintaining an independent government until 25 August. Since the establishment of Florentine dominion in 1384, there had been a number of attempts to restore independence to Arezzo. At the core was normally a group of malcontented patricians, resentful of Florentine dominance, of the loss of communal liberty and of exploitative taxation. In 1502 there were several problems which rendered Florentine control over Arezzo particularly precarious. Florentine territorial authority was seriously weakened by the successful rebellion of Pisa in 1494, followed the next year – and even closer to Arezzo – by the loss of Montepulciano to Siena. Attempts to regain these dominions exhausted Florentine resources, and, moreover, there is documentary evidence that Pisa and Montepulciano provided examples for Arezzo in 1502. Another problem was that in 1502 gram was in short supply in Florentine dominions and it had been necessary previously to move substantial stocks to feed Florentine troops lodged near Borgo San Sepolcro and needed to protect against a possible attack from hostile forces in Umbria; there was considerable anxiety among the Aretine populace lest the Florentines should do this again and leave Arezzo to starve. Another difficulty for Florence was the weakness of local support.
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