For a small city, Montalcino has a large share of history. Her citizens were proudly anti-fascist in the 1920s, and they stubbornly resisted the Germans during World War II. But her proudest moments occurred during the frequent clashes of the Renaissance's great city-states.
Italy was not then a nation but a territory warred over by powerful foreign neighbors and her own city-states. Montalcino, like many other small towns was a pawn in their struggles, useful as a base from which to protect themselves and harass their enemies. Montalcino's star turn came in the 1550s, at the end of the serial warfare between brilliant Siena and the tyrannical, power-hungry Medici princes of Florence.
Montalcino had prospered and grown during her long alliance with Siena; her people had won Sienese citizenship and built their mighty walls and fortress. In 1553 the armies of Cosimo de' Medici and his Spanish allies attacked. Their assault on the fortress failed and the Montalcinesi refused to surrender despite three months of siege.
Two years later Siena fell, but her leaders escaped. Montalcino defiantly gave shelter to them and their ideals of freedom, knowing full well that the government-in-exile--the Republic of Siena in Montalcino--would enrage the Medicis. Volunteers (today we'd call them freedom fighters) arrived from as far off as Piedmont to defend Montalcino, but they were not enough.
In the end, Montalcino fell as much from peace as from war: When France (Siena's ally) and Spain (Florence's) came to terms, embattled Montalcino was helpless, and soon the Medici crest was hung on the fortress wall, where it remains today. That began a long decline for the city; it lasted centuries and was ended only by a development in the world of wine: the creation of Brunello di Montalcino.
The region's farmers had made wine for centuries. Their red, called vermiglio, played a small role in the siege of 1553, when the garrison commander, pale with tension and hunger, rubbed it into his cheeks, thus simulating a healthy complexion to reassure his troops. In the 1600s, the English kings Charles II and William III favored a wine they called "Mont Alchin." Moscadelletto, a sweet white dessert wine, was praised by the poet Francesco Redi - and re-created, in our own time, as a moscadello Banfi calls "FloruS."
A breakthrough came in the late 1800s, when attention was focused on the Brunello grape (it was actually Sangioveto Grosso, a clone of Chianti's Sangiovese). This superior variety, carefully handled and extra-aged, yielded superior wine, but news spread slowly because Italy's reputation in the wine world was held down by overproduction and lack of regulation.
Market success began in the 1960s. DOC regulations gave quality a chance to stand out, and Brunello won DOC status in 1966 (it became the first of the elevated DOCG wines in 1980). Its "little brother," Rosso di Montalcino, from the same grape (but aged only one year instead of four), showed enough class to win DOC rank in 1984.
Thus has Montalcino awakened from its long sleep. It's still a quiet little city, but that's mostly because the wine speaks for itself.