Federico da Montefeltro visited Anghiari on two distinct occasions at a distance of six years, the first time in September 1468 and the second on July 5th 1474. The most significant presence appears however to be that of 1468, when the Duke of Urbino with his second wife Battista Sforza and the court were guests of Mazzone di Gregorio and Francesco Prospero, both Anghiarese Men-of-arms who fought with Federico da Montefeltro. There is a curious chronological coincidence relating to Mazzone’s family: his father Gregorio, who took part with Federico of Urbino in the capture of Piombino in 1448, died exactly in September of that same year. This far from demonstrates that the Mazzone family’s mourning was the motive for Federico’s presence in Anghiari, but none the less it remains an important record.
Equally important subsequently was the presence of Anghiarese companies under the command of Federico at the siege of Volterra in 1472, a military action commissioned by Lorenzo the Magnificent because of a dispute between Florence and Volterra due to a quarrel over the exploitation of a mine. With the Duke of Urbino there were at least three Anghiarese companies: that of Matteo Taglieschi, another of Anghiarino and finally the company of Iacopo Giusti, (the latter being the son of Giusto Giusti, the solicitor who was a close friend of Cosimo de’Medici the Elder). The city was won by pacts but the inhabitants were brought to obedience by the violence of the soldiers who sacked it. In 1473, when the hostilities ended, Iacopo Giusti was appointed castellan of Volterra with an elevated remuneration: 150 gold florins per year. The following year Federico passed through Anghiari, on his way back to Urbino. We see therefore, an interesting chronological succession between the passages of the Duke and the facts regarding the Anghiarese men of arms. Equally important, but still to be investigated, are the records of the marriage between a daughter of Gentile Brancaleoni and the Anghiarese constable, Agnolo Taglia, the deed for which was drawn up by the notary Giusto Giusti in October 1440. Gentile Brancaleoni was the first wife of Federico da Montefeltro.