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In the mid-13th century, Tuscany was a battleground in the struggle between the Empire and the Papacy. Rumours have long swirled around the emperor’s sudden passing, from poisoning to a murder plotted by another of his illegitimate sons, Manfred. With the Emperor gone, the Ghibellines lost their central figure, while the popes continued to exert pressure and assert the sacred rights of the Throne of St Peter. The wars between Guelphs and Ghibellines had only just begun.
From the manuscript of Giovanni Villani, Nova Cronica (14th century), ms. Chigi L VIII 296, fol. 84r, Vatican Apostolic Library
An empty throne
Frederick II’s death left a political vacuum that rocked both the Empire and the Kingdom of Sicily. He also left behind a host of legitimate and illegitimate children, soon to be embroiled in a struggle for the throne. His many relationships—with three official wives, one morganatic wife, and several lovers—produced roughly twenty heirs, all in some way recognised and woven into the Swabian power network.
miniature in manuscript (?), Bibliothèque Nationale de France
Predictably, this sparked no small amount of turmoil over the succession. Upon Frederick’s death, two distinct wills came into play: the first, from May 1228, was drawn up before his departure on crusade, while the second was recorded in his final moments. Both reiterated his wish to keep the Kingdom of Germany united with the Empire. In the first, the title would pass to Henry VII, who had died in murky circumstances as far back as 1242. In the second, the succession went to Conrad IV—his son by his second wife—stipulating that, if he left no heirs, Henry Carlotto (the eldest son by his third wife) and Manfred would inherit. Manfred, Frederick’s only son with Bianca Lancia, was granted “the power […] of Conrad in Italy and particularly in the Kingdom of Sicily’ with ‘full authority to do everything our own person might do, as if we were still alive”[1], namely sovereign powers in Italy and Sicily while Conrad was absent.
Nonetheless, when succession became an open question, Pope Innocent IV rejected Frederick’s testamentary instructions, deeming his plan to unite the Kingdom of Germany and the Kingdom of Sicily illegitimate, insisting Sicily was a papal domain. From then on, constant clashes arose, particularly because Manfred—Frederick’s natural son—never relinquished his claim to the Sicilian throne and fought for its recognition by any means necessary. Villani alleges Manfred bribed physicians “per moneta e gran promesse” (“with money and great promises”) to poison Conrad “in un uno cristeo” (“with an enema”)[2].
Richard de Montbaston (1337), miniature from Manuscript Français 22495, Bibliothèque Nationale de France
Guelphs and Ghibellines between Tuscany and Sicily
Whether fact or smear, Conrad’s death opened a new front in the struggle for the Kingdom of Sicily. Manfred tried negotiating with the pope, pledging to uphold the rights of Conrad’s son, Conradin (Corradino), yet as soon as he had the chance—thanks to his Saracen troops at Lucera and the recovered imperial treasury—he had himself crowned in Palermo in 1258. To bolster his rule, he renewed ties with Ghibelline factions in central and northern Italy, intensifying an already fragile situation.
Meanwhile, Tuscany was aflame with tension. The Guelphs regained influence after Frederick’s death as the Ghibellines sought to preserve their link to Swabian authority. In Florence, the Guelphs returned to the city, secured dominance over strategic sites such as Volterra and San Gimignano, and put the Ghibellines in Arezzo on the defensive. Pisa, loyal to the Empire, was forced to contend with Florentine aggression and internal rivalry between the Della Gherardesca (Ghibellines) and the Visconti (Guelphs). Siena, for its part, received orders from Manfred (via Galvano Lancia) to seize Aldobrandeschi lands, as the Aldobrandeschi were known foes of the Swabians. It was an opportunity to strengthen Siena’s presence in the Maremma, where Grosseto and the local nobles—though nominally pro-imperial—fell effectively under Siena’s expanding sway.
Come June 1251, just as Tuscany’s political balance was being realigned, the Ghibellines prepared a methodical move. Their most influential figures gathered secretly in a hut by the Via Francigena at the foot of Castiglione in Val di Strove. Among them were powerful families like the Alberti, Brunelleschi, Uberti, Amidei, and Scolari. Their goal? To forge a hidden pact aimed at bringing Tuscany under Ghibelline control[3].
There, exiled pro-imperial Florentines allied with Siena, Pisa, and Pistoia, forging a long-term agreement. The objective was clear: to form a ‘fifth column’ capable of destabilising the Comune of Florence, perhaps from within, if the chance arose. Their plan also allowed for the possibility that Ghibellines in Florence might remain in exile or under house arrest for lengthy intervals, enduring heavy economic losses. From today’s standpoint, this might sound like blatant treason, but we must remember that in the Middle Ages the “Comune” did not represent the entire populace: those who felt excluded believed they had every right to fight the opposing party by whatever means.
War on everyone’s mind
Their pact promptly bore fruit: on 30 July, Counts Guidi joined the league, pledging Siena immediate aid if hostilities erupted on the Aretine border. Earlier, the Ghibellines of Arezzo had promised to join in with 200 fully armed knights, infantry, crossbowmen, and skilled siege troops[4] funded by Siena, Pisa, and Pistoia—who also vowed to repair battered fortresses and shelter future exiles. In November 1251, certain aristocrats from Montalcino likewise submitted to Siena, pledging to act against Montalcino itself whenever Siena commanded. In exchange, those Montalcinese nobles demanded 700 lire for their losses and another 700 for their permanent departure from Montalcino, vowing neither they nor their descendants would ever set foot there again. The matter of Montalcino would later spark a brutal battle, but that will come in future posts.
At the time, Siena was indeed under Ghibelline rule, but with a keen sense of caution. Provenzano Salvani, a leading figure of the anti-Florentine party, warned the General Council not to act rashly or embark on unplanned military campaigns—at least until year’s end—since the city was not yet prepared for open war. Solid alliances were lacking, particularly among the mountainous nobility with their fickle allegiances. The Ghibelline leader travelled from one fortress to the next, meeting the Florentine rural lords, then venturing as far as Perugia, Massa Marittima, and Torrita, and negotiating with Poggibonsi to prevent it from becoming too closely tied to Florence. There was no doubt about it: war was on everyone’s mind, but it was equally clear that every move had to be thoroughly prepared in advance.
Meanwhile, Florence was hardly idle. In July 1251, it attacked Pistoia with Prato’s support, while Lucca hit Pisa in the Versilia region and Pisa countered in the Val di Nievole. The chronicler Giovanni Villani recorded that Florence defeated the Ubaldini in Mugello that same year, describing 1251 and the next as an uninterrupted series of Guelph victories: sieges, battles, and skirmishes in which the Florentines nearly always prevailed. The Anonymous Sienese, however, paints a different picture, touting spectacular successes for the Ghibelline League: Monte San Savino and other Aretine strongholds supposedly fell in 1251, and at Pontedera in 1252, Siena and Pisa claimed victory. Events at Montaione only add to the confusion, where “‘the podestà of Siena fell, and many among the citizens as well”[5], pointing to a fierce confrontation that Siena boasted of winning. Both sides, however, agree on one point: at Montalcino, Siena suffered a clear defeat. Ghibelline sources refer to it as a “rebellion” by the castle, yet it seems Montalcino was merely trying to free itself from Siena’s influence by allying with Florence.
1254: the victorious year of Florence
By around 1252, the theatre of conflict had expanded even further. Florence adopted a new emblem—a red lily on a white field (as opposed to the exiled Ghibellines’ white lily on red)—and was joined by Lucca, Genoa, and Orvieto, all driven by concerns over Pisa or Siena. The Guelph’s successes at Pontedera and Siena’s failures motivated exiled Florentine Ghibellines to reconcile with their home city, and many exiles returned in a temporary truce.
That year also saw the minting of the Fiorino d’Oro, Florence’s gold coin which soon became the most powerful and widely used currency of the Middle Ages—a symbol of the city’s economic might that infuriated King Manfred, convinced that only a sovereign was entitled to strike gold coins. In any event, in the wake of the latest upheavals, those who had conspired in the hut at Val di Strove promptly became keen on peace: Farinata degli Uberti, Guido Novello dei Guidi, the Pazzi, the Lamberti, and several others all signed a non-aggression pact. From their perspective, launching a civil war under such disadvantageous conditions seemed far too risky.
Florence reached a decisive turning point in 1254. Villani calls it the ‘marvellous year’ or ‘victorious year’ for the city of the red lily[6], , as it captured new castles and cornered Pisa. Among its bolder targets was Monteriggioni, defended by a German garrison ready to switch sides for 50,000 lire. Yet the Florentines managed to gather only a little over 20,000, even with the generosity of some twenty prominent citizens, and so the siege ended without surrender.
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Fiorino d’Oro (Golden Florin) from the collections of the Nickle Galleries, University of Calgary, Canada.
It hardly mattered, because around that same time Florence took Poggibonsi, seized Volterra, and compelled Pisa to negotiate – gaining Ripafratta and nearly Piombino, believed essential for sea access. The Florentine chronicler lamented that the city did not press for Piombino, for “troppo n’acrescea la città di Firenze” (“‘for it would have greatly benefitted Florence”). Sienese sources, by contrast, downplayed these conquests, stressing that their army came within a kilometre of Florence’s walls and seized prisoners and livestock until a fresh threat from the Aldobrandeschi forced the Sienese to withdraw.
Turmoil in Siena
Even amidst hostilities, the popular classes in Siena took advantage to assert themselves further in the city’s institutions. In 1253, amid war, they elected their first Capitano del Popolo, signalling that the Ghibelline League’s administration could no longer remain solely in the hands of the great families. With these shifts in motion, a peace treaty was struck in 1254 between Florence and Siena. The Anonymous Sienese writer explains that Florence wished to expand its territory, while Siena, confronted with rising costs and risks, preferred to focus on defeating the ‘tyrants’—the feudal lords of the mountains and Maremma, above all the Aldobrandeschi, impossible to subjugate permanently.
On 8 June of that year, with notary Brunetto Latini serving as a mediator, a decree was issued calling for an end (on paper at least) to all aggression, arson, abductions, and demolition. A side note for literary enthusiasts: Brunetto Latini, then barely in his thirties, would one day become the mentor of the most famous poet of all, Dante Alighieri. We may discuss that in due course.
Yet this ceasefire did not last. Pisa, beset by Florence, Lucca, and Genoa, introduced more popular representation into its governance in search of new allies but was soon beaten again by Florence and Lucca at the Abbey of San Savino. In 1256, the Pisans broke their agreements by attacking Lucca, prompting Guelph forces to push right up to the walls of Pisa. The following year, Florence razed Poggibonsi—suspected of collusion with Siena—and once again tensions arose.
War clouds looming
In 1258, the Ghibellines launched another attempt: at King Manfred’s urging, according to Villani, the Uberti tried to seize Florence. The Guelphs responded savagely, killing Schiattuzzo degli Uberti in battle, capturing his companions, and then swiftly beheading them. Several families (Amidei, Guidi, Lamberti, Scolari…) fled to Siena, which welcomed them without heed to the recent peace treaty. Even worse, the Florentines had the Ghibelline abbot of Vallombrosa, Beccheria da Pavia, put to death, though he was said to be an upright man with no genuine crime. A sentence that would come at great cost to Florence.
The pope excommunicated the city and placed it under interdict, and many were certain that God’s punishment would soon befall Florence—which, as we’ll see, was not far from the truth. Siena, meanwhile, claimed it had been betrayed by Florence and readily received the exiles. Arezzo, governed by a podestà of Florentine birth, seized the opportunity to attack and conquer Cortona in 1259, prompting Florence to occupy the castle at Gressa, belonging to the bishop of Arezzo. If there had ever been any genuine desire for peace, these events obliterated it, plunging the region into another downward spiral of conflict.
This mounting cycle of violence—spurred on by the ambitions of the city elites and the absence of any universally respected authority—set the stage for a new, large-scale war between the Guelphs and the Ghibellines. Alliances and peace treaties, however grandly declared, were soon shattered, dragging the city-states into relentless strife, where each victory presaged another torrent of devastation and vengeance. Before long, beautiful, fertile Tuscany would be awash in the blood of thousands of its sons, cut down on the field at Montaperti.
Bibliography
- Anonymous. (n.d.). Cronaca senese (14th century). As cited in Balestracci, D. (2017). La battaglia di Montaperti (p. 27). Laterza.
- Balestracci, D. (2017). La battaglia di Montaperti (p. 49). Laterza.
- Canaccini F. (2010) Restano i termini, mutano i significati: Guelfi e Ghibellini. L’evoluzione semantica dei nomi delle fazioni medioevali italiane. In: Lotta politica nell’Italia medievale, 85-94
- Cardini, F. (2007). Breve storia di Firenze. Pacini.
- Caleffo Vecchio. (n.d.). Volume II, pp. 740–742. As cited in Balestracci, D. (2017, pp. 42, 45). La battaglia di Montaperti. Laterza.
- Davidsohn, R. (1956–1968). Geschichte von Florenz (Vol. 1). Firenze.
- Montauri, P. di T. (Attributed). (n.d.). Cronaca senese (pp. 192–193). As cited in Balestracci, D. (2017, p. 48). La battaglia di Montaperti. Laterza.
- Pispisa. (n.d.). Il Regno di Manfredi (p. 11). As cited in Balestracci, D. (2017, p. 35). La battaglia di Montaperti. Laterza.
- Villani, G. (1991). Nuova Cronica (G. Porta, Ed.). Fondazione Pietro Bembo/Guanda.
[1] Pispisa, Il Regno di Manfredi, p.11, as mentioned in Balestracci D., La Battaglia di Montaperti, Laterza, 2017, p.35
[2] Villani G., Nuova Cronica, VII, 44
[3] Caleffo Vecchio, II, p. 740-742, as mentioned in Balestracci D., La Battaglia di Montaperti, Laterza, 2017, p.42
[4] Caleffo Vecchio, II, p. 740-742, as mentioned in Balestracci D., La Battaglia di Montaperti, Laterza, 2017, p.45
[5] Cronaca senese conosciuta sotto il nome di Paolo di Tommaso Montauri, pp. 192-193, as mentioned in Balestracci D., La Battaglia di Montaperti, Laterza, 2017, p.48
[6] Balestracci D., La Battaglia di Montaperti, Laterza, 2017, p.49
