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The conflict between Florence and Siena reached a pivotal moment. Two massive armies were ready to march for war, both seeking a decisive showdown: on one side, Siena, convinced it could subdue Montalcino and Montepulciano with Manfredi’s backing; on the other, Florence, which—despite internal divisions and the potential inconsistency of its allies—had formed a cohesive bloc, ready to prevail.
In the summer of 1260, the Florentines believed they had a genuine chance of success, despite conflicting signals coming from the field. They crossed the boundaries of Florence’s territory and marched resolutely into the Valdorcia. The decisive encounter was now only a short way off, the brutal fight that went down in history as the Battle of Montaperti.
Conflicting sources regarding Montaperti
The story of the Battle of Montaperti, and indeed of the entire conflict between Siena and Florence, rests on the few surviving chronicles—documents written decades after the events they describe. Moreover, they were shaped by their own times: as we have seen in earlier posts, the chroniclers of that era lived and breathed their city’ spirit, and factional rivalries around them, often producing contradictory accounts. My aim, then, has been to piece together these various sources, presenting both viewpoints: that of Siena and that of Florence.
The Sienese Chronicler
According to the Anonymous Sienese Chronicler, it all began when Florence’s army, having come to Montalcino’s aid, halted near the walls of Siena. From there, the Florentines sent an ambassador into the city with an ultimatum: the Sienese were to open three breaches in their walls and surrender within three days, or else the city would be razed to the ground. This demand, which may sound strange to modern ears, carried both symbolic and legal weight at the time. If you entered a city after tearing down its walls, it was wholly yours, by virtue of the strongest right known back then—the right of conquest. Such a brazen, intolerable stipulation was impossible for Siena’s rulers to accept. According to the account, they anxiously investigated whether the Commune had sufficient funds to pay for an army ahead of the looming battle, only to discover that they did not.
Help arrived in the form of one of the city’s wealthiest citizens, the merchant Salimbene Salimbeni. He had his coffers brought on a gaily decorated cart to the church of San Cristoforo, right in front of the Florentine ambassadors, and laid bare their contents: one hundred thousand florins, more than 350 kilograms of gold (771 lb) – a massive sum worth well over thirty million dollars today. The Sienese authorities then informed the Florentines that they rejected their ultimatum and that it would be wise for them to prepare for war, as they would soon meet on the battlefield – “e proveremo se sarete tanto forti quanto vi fate”, and we shall see if you are as strong as you claim.
The Florentine account
As one might expect, the Florentine account, as recounted by Giovanni Villani, paints a very different picture. According to his version, everything started with an elaborate plan hatched by the undisputed leader of the Ghibellines recently expelled from Florence: Manente degli Uberti, better known as “Farinata,” owing to his fair, chickpea-flour-coloured hair. He allegedly believed it impossible to wrest control of Florence from the Guelphs without solid external backing. Thus, Farinata sought help from King Manfredi of Sicily. As we shall see in future posts, the king was already burdened with other pressing matters and could only spare one hundred of his formidable German knights. Farinata degli Uberti refused to be disheartened: “Do not let this discourage you; we shall accept any help he can give, no matter how small. Let him grant us, at least, the honour of his banner”.[1]
This brings us back to the sortie of those hundred German knights we mentioned in the previous episode, remember? In the spring of 1260, when the Florentines showed up brazenly at Siena’s gates, it was Farinata who hosted a banquet for the German knights, plying them well with wine and urging them to strike at the enemy camp. The Germans charged, taking the Florentines by surprise. For a moment, this sudden assault brought the Ghibellines some success; yet, when the Guelfs saw how small Manfredi’s contingent truly was, they rallied and turned the tables. Most of the Germans, left isolated, were slain; Manfredi’s standard was seized and carried off in triumph to Florence. What looked like a clear Florentine victory was, according to Villani, all part of Farinata’s grand design: his real aim was to wound King Manfredi of Sicily’s honour, prompting him to react with far greater force against the Florentine enemy.
The plan worked brilliantly: another embassy was dispatched to Sicily at once. If Manfredi had previously dismissed their request, the news that his banner had been lost now stung him to the core. He agreed to send 800 knights to Tuscany, led by his kinsman, Count Giordano d’Agliano—the same Count mentioned in the Sienese merchant’s letter. The king paid half the knights’ wages, while Siena—according to Villani—covered the rest, borrowing 20.000 gold florins from the Salimbeni family in exchange for pledges over certain castles.
Farinata’s grand design
Weeks went by, however, and the German knights lingered in Siena without fighting, draining the Commune’s purse with their costly contracts. With each day of inactivity, the three-month term of their hire drew nearer, threatening that Manfredi might recall his men. Once more, Farinata degli Uberti pulled a trick from his sleeve: a cunning ruse meant to prod Florence into war. This time, Villani tells of certain friars – “two wise Franciscan brothers”[2] who were secretly sent into the city to convince the Florentine leaders that some noble families in Siena, weary of figures such as Provenzano Salvani, were prepared to open the gates at night for 10,000 gold florins. The friars themselves were unaware of the deception: they simply passed on what they had heard, and the Florentines fell for it.
In Giovanni Villani’s telling, Florence took the bait completely. Not only did they gather the 10,000 florins, but, at a heated council, they decided to march on Siena under the pretext of bringing supplies to their ally, the castle of Montalcino. The opportunity seemed too good to miss, and a few seasoned Florentine nobles—such as Count Guido Guerra and Tegghiaio Aldobrandi degli Adimari—tried to temper the excitement. They warned that the German knights were in Siena, and the events of that spring—when even a small detachment of Manfredi’s fearsome cavalry had put the Guelf ranks in crisis—had already laid bare their power. But no one listened. Those who questioned the plan were ridiculed as cowards, and repressive measures were even threatened against anyone who opposed the urge to depart immediately. Villani preserves a snippet of conversation in which one expedition supporter, a certain Spedito—“a very presumptuous man”—gave his opinion in the council and then turned to Tegghiaio Aldobrandi, saying in crude language that he should pull down his trousers if he was so frightened that he was about to soil himself. Messer Tegghiaio, in turn, replied that, should the time come for war, Spedito would lack the mettle to follow him into the thick of battle, “where I myself shall fearlessly plunge.”[3]
The proud populace had chosen war. The grand army under the red lily on a white field was hastily mustered, allies were summoned to join them for the imminent battle, and, after a forced march, the Florentines encamped near the plain of Montaperti, beside a stream called Arbia. There, they waited hopefully for Siena’s gates to open all of a sudden. Before long, they bitterly discovered there would be no open gateway; instead, out of that very gate poured the Germans and the Sienese, fully resolved to engage in combat.
Siena’s frantic mobilization before battle
Returning to the Sienese chronicles, we find another author, Paolo di Tommaso Montauri, who expands on the Anonymous Sienese’s account, turning it almost into the script of movie. He describes the intense meeting of Siena’s leaders once they learned of the Florentines’ looming arrival. Some fearful citizens proposed yielding rather than risk a massacre, while others—like Provenzano Salvani—were adamant that they must fight. In the end, they chose to stand firm: Buonaguida Lucari led a procession, stripping himself of his garments, hooded and wearing a rope around his neck, walking barefoot to the Cathedral to implore the Virgin’s protection. With bishop and notaries in tow, this ceremony became a grand stage for the entire community: the Sienese renewed their peace among themselves, entrusted the city to the Madonna, and embraced one another as a sign of unity.
A frantic mobilisation immediately followed: the Germans purchased leather and sundry supplies, stitching harnesses and armour at speed with help from artisans, tanners, carpenters, and tailors. Even the preachers recruited priests and friars, some to offer spiritual comfort, others ready to join the fight and stain their hands with Florentine blood. Late in the day, the bulk of their army set up camp not far from the Guelf lines, and supplies arrived in the form of chickens, roasted meats, and copious wine. Roasted meat, so they said, gave more strength and fuelled one’s thirst, “facendo l’uomo più vigoroso” – making a man mightier. Throughout the night before the battle, Montauri writes that the Sienese launched raids and skirmishes, keeping the Florentines on edge and depriving them of rest. Under mounting pressure from the enemy, the Florentines found no sleep that night.
The Battle of Montaperti
On the morning of September 4th, 1260, the Ghibelline army crossed the Arbia torrent and took up position in the beautiful hills of Montaperti. It is said it was strong with eighteen hundred knights and eighteen thousand infantrymen; in addition to the Sienese troops, commanded by Provenzano Salvani, there were contingents from the cities of Massa and Pisa, the exiles from Florence, and the formidable German mercenary knights, led by Walther von Astimberg.
Battle formations
On the other side, the Guelph ranks could count on a large Florentine contingent, supported by troops from the cities of Lucca, Perugia, Bologna, San Gimignano, and many others: more than three thousand knights and thirty thousand infantrymen, with the hilly terrain to their advantage. The Ghibelline forces were numerically inferior and organised into four distinct groups: the first, a mix of imperial infantry and knights, was commanded by Count d’Arras; the second, an avant-garde of twelve hundred men, was under the guidance of Count Giordano d’Agliano; the third, composed of Sienese troops, was directed by Aldobrandino Aldobrandeschi and had to confront the enemy directly despite the unfavourable descent; the fourth, a group of two hundred knights led by Niccolò da Bigozzi, had the task of defending the “Carroccio”.
If you read my previous post, you will be familiar with the term: this was a large four-wheeled cart bearing the city’s insignia, the symbol of unity and determination for the militias, and a useful point of reference in the confusion of battle. Anyway, the agreed strategy provided that the second and third divisions would engage the Guelph front and, at the agreed signal, allow Count d’Arras’s troops to encircle and attack the enemy from behind.
The legend of Walther von Astimberg
There are many legends about this battle, and one that I want to begin with is that of Walther von Astimberg. The German knight obtained from the Ghibelline High Command the honour of being the first to do battle, charging lance in hand at the enemy formation. At the head of his cavalry, at first, advancing cautiously towards the enemies, von Astimberg launched the attack with the lance ready against the captain of the troops from Lucca, piercing him through and through. Having extracted the lance from the body, he brought down two other knights and, once he lost the weapon, drew his sword, continuing to make his way among the enemies. His infantry followed him but soon found themselves in difficulty: the Guelph infantry, after resisting the initial attacks of the Ghibellines, launched a counterattack.
Beginning of the battle: the Sienese knights launch the attack – Niccolò di Giovanni di Francesco di Ventura. (1442–1443) La sconfitta di Monte Aperto, fol. 13v. Biblioteca Comunale degli Intronati, Siena, ms. A.IV.5.
This move forced the fourth division, commanded by Niccolò da Bigozzi, to deviate from the orders received and to intervene in battle, thus abandoning the protection of the Sienese carroccio. The battle had turned into a bloody hand-to-hand struggle: the Florentines stood their ground with dogged resolve, while the Sienese host hurled itself upon them. By all accounts, it was a slaughter so overwhelming that the chroniclers themselves struggled to convey its horror. Amidst the carnage, one figure stands out: a woodcutter named Geppo, who, wielding his axe, is said to have slain more than twenty Florentine soldiers.[4] It was in that dramatic phase of the battle that, according to Villani, the Ghibelline infiltrators among the Guelphs consummated their betrayal.
The massacre, and the betrayal of Bocca degli Abati
Jacopo de’ Pazzi the Elder, a valiant Florentine knight, had received the honour that day of carrying the Guelph insignia. He watched the unfolding battle, perhaps too focused to notice that beside him another knight, Bocca degli Abati, had drawn his sword: and with a single strike, he cleanly severed the hand holding the standard.
The Guelph insignia fell to the ground, while from the Ghibelline ranks rose the cry of “Saint George!”: it was the signal Count d’Arras was waiting for to launch the cavalry behind the enemy. The Guelph ranks suddenly found themselves in panic, and when the Count himself killed the Florentine commander-in-chief, Iacopino Rangoni, the Guelph formation broke. A massacre began that lasted until nightfall, so bloody that, quoting Dante, “the carnage and the great havoc made the Arbia coloured in red”[5]. Ten thousand Guelphs died that day, and fifteen thousand were taken prisoner, while the banner of Florence was dragged in the dust attached to the tail of a donkey.
The aftermath of Montaperti
Once the battle was over, the Sienese army returned to the city on the 5th September, bringing with them Guelph banners, carts filled with weapons taken from the enemy, and the bell of the Florentine carroccio—while their own carroccio was carried into the cathedral like a sacred relic. Even now, you can see the two “masts” that once held the victorious banners, embedded in the columns of Siena’s Duomo. Immediately the mockery of the vanquished began: the Anonymous Chronicler tells us of a Florentine ambassador paraded into Siena on a donkey, seated backwards with his face to the tail, an easy target for children’s jeers. Then came the ritual of displaying prisoners—thousands, according to Montauri—while the Sienese populace, gathered in solemn procession, once again gave thanks to the Virgin Mary, Mother of God. Once the euphoria subsided, came the matter of ransoms: anyone seeking freedom had to pay in solid gold and, according to Montauri, also procure a goat to be sacrificed at Fontebecci, a spot north of Siena’s main gate.
The battle was over, but not the war. That very evening, while the surviving Florentines withdrew in disarray towards their own territory, the Sienese army and its allies were already considering how to capitalise on their victory and take vengeance on those they believed had betrayed them. Once the prisoners’ fate was decided, attention shifted to Montalcino, deemed by the Sienese to be the real cause of the war. Count Aldobrandino di Santa Fiora called for retribution, branding the rebellious strongholds as breeding grounds of unrest; by contrast, other citizens opposed prolonging the conflict, convinced that a humiliated Florence would soon recover and that victory might invite further trouble. Yet the hard-line stance prevailed—that of the noble Provenzano Salvani, effectively at the helm of Siena—who insisted Montalcino must be made to pay for its support of Florence.
The fall of Montalcino
The Ghibelline commanders lost no time. Within weeks, they led their forces beneath the castle walls and laid siege. After a week of stalemate, on 30 September, the Sienese attacked, heaping bundles of kindling against the city gates and setting them alight. Alarmed at the prospect of being assailed from multiple sides—or seeing their settlement engulfed in flames—the defenders of Montalcino attempted a sortie. It was futile: lacking a precise strategy, they smashed against the Sienese ranks, and were cut down by a storm of crossbow bolts. Their sole chance had passed. With the gates now little more than smoking embers, the Sienese army crashed in. “Long live the Commune of Siena, death to the treacherous people of Montalcino!”[6] hey cried, sacking the town.
Once the fortress had fallen, some inhabitants who survived fled into Florentine territory; others, fearful of being left without a homeland, went instead to Siena in hope of some mediation. A sorry sight indeed—the line of exiles, rope around their necks, clad only in their shirts, weeping before Siena’s gates. The Sienese agreed to let them enter on one condition: that they see for themselves the harm they had caused. They were taken onto the plain of Montaperti, still covered with unburied corpses. According to Montauri, they were left there among the rotting carnage, the stench of decay rendering the air unbearable, to reflect on the consequences of their actions. The Anonymous Sienese Chronicler adds that they were forced to dig mass graves for the thousands of victims.
For Florence, news of that surrender was devastating: Montalcino had been a vital Guelph stronghold, and now it had fallen into the victors’ hands. Florentines grew ever more anxious, fearing a domino effect: if one pro-Florentine fortress after another collapsed, the city would lose its last footholds in the territory and become further weakened. They knew all too well that the war was far from over, and that the Sienese-imperial alliance would strike at whatever Guelph supporters still remained in the countryside. Mensano, a castle seized by Florence in previous months, was the next to fall: its walls were torn down, and an inquiry was immediately launched to identify those responsible for switching to the Guelph cause. Then came Montepulciano, another strategic border castle, forced to accept similar terms of surrender.
One castle after another was ordered to demolish its towers, defences, and ditches, causing the map of Florence’s outposts to crumble. The city of the lily looked on as its strongholds toppled one by one, unable to resist because, after Montaperti, the communal army lay in disarray. Matters quickly worsened when yet another shadow fell over Florence: the possibility that Siena, together with other Ghibelline cities of Tuscany, might even pursue the destruction of its rival. Florence’s fate would be decided by the victors, gathered in council at nearby Empoli.
Bibliography
Primary Sources
- Alighieri, D. (2016). Divina Commedia: Inferno (A. Andreoli & P. M. C. Rizzo, Eds.). Mondadori.
- Montauri, P. di T. (Attributed). (2002). Cronaca senese (C. Giunta, Ed.). In L. A. Muratori (Series Ed.), Rerum Italicarum Scriptores, nuova edizione (Vol. 15/6). Salerno Editrice.
- Villani, G. (1991). Nuova Cronica (G. Porta, Ed.). Fondazione Pietro Bembo/Guanda. (Original work published ca. 1348)
Secondary Sources
- Balestracci, D. (2019). La battaglia di Montaperti. Editori Laterza.
- Spagnolo, A. (2004). La sconfitta di Monte Aperto: una cronaca e un cantare trecenteschi. Nuova Immagine Editrice.
[1] “messer Farinata degli Uberti disse: «Non vi sconfortate, e non rifiutiamo niuno suo aiuto, e sia piccolo quanto si vuole; facciamo che di grazia mandi co·lloro la sua insegna, che venuti a Siena, noi la metteremo in tale luogo, che converrà ch’egli ce ne mandi anche”; e così avenne»”.
Giovanni Villani, Nuova Cronica, VII, 74
[2] Giovanni Villani, Nuova Cronica, VII, 77
[3] “Il sopradetto Spedito anziano, uomo molto prosuntuoso, compiuto il suo consiglio, villanamente il riprese, dicendo si cercasse le brache, s’aveva paura. E messer Tegghiaio gli rispuose ch’al bisogno non ardirebbe di seguirlo nella battaglia colà ov’egli si metterebbe.”
Giovanni Villani, Nuova Cronica, VII, 77
[4] “Fuvi uno che aveva nome Geppo, che cor una scure n’amazò più di vinti; e quello Geppo andava per Siena spezando le legna: or pènsate come facevano quegli prodi cavalieri! Lo macello degli uomini e de’ cavalli non si potrebe dire quanto era.”
Spagnolo A. (2004), La Sconfitta di Monte Aperto, Siena p. 169.
[5] “Ond’io a lui: “Lo strazio e ’l grande scempio
che fece l’Arbia colorata in rosso”
Dante Alighieri, Comedìa, Inferno, X, 85-86
[6] “Viva el comuno di Siena e muoia questi traditori Montalcinesi”
