In 1553, the city of Montalcino was besieged for a fifth and last time in its history by Imperial and Medicean troops headed by the Spanish commander Don García de Toledo.
After 80 days of fighting, they gave up and abandoned the siege. And Montalcino was a free city.
After the city of Siena fell to the Medici and the Spanish, in April 1555 more than four hundred families of Sienese exiles sought refuge in the Free Township of Montalcino and gave life to the “Repubblica di Siena in Montalcino” (“The Republic of Siena at Montalcino”). They adopted laws and civic ordinances similar to those of their native city.
And so Montalcino became at once the capital of a historic and ancient state and the last free township in Italy.
A mint was built under the loggia of the Palazzo Comunale and coins were forged out of gold, silver, and copper.
One of these was a gold scudo with a shewolf and the inscription R[es] P[ublica] Sen[ensis] Ilcino (Commonwealth of Siena at Montalcino) on the obverse and on the reverse HENRICO II AV[spice] (under the auspices of Henry II). In the center of the reverse, there was an oval shield inscribed with the motto Libertas (freedom).
On the obverse of the teston,* there was the inscription R. P. IN ILICI. HENR. II AVSP and on the reverse, the Virgin Mary with the inscription TUO CONFISI PRAESIDIO (entrusted to your protection).
* “A silver coin struck at Milan by Galeazzo Maria Sforza (1468–76), bearing a portrait or head of the duke, and called in Italian testone; then of the similar coin struck by Louis XII after his conquest of Milan, for currency in Italy, and by Francis I (1515–47) for use in France. Both in Italy and France, the name was soon applied to equivalent silver coins without a portrait; but always to pieces heavier than the gros” (Oxford English Dictionary).