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Tuscany, mid-14th century. A 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, foretelling another torrent of devastation and bloody vengeance.
The context
Siena and Florence were manoeuvring their pieces across the vast Tuscan chessboard, both convinced that securing dominance over those lands required the other’s destruction. Their brutal contest was nearing its final moves, with the fortresses of Montalcino and Montepulciano caught in the middle.
Both strongholds were looking to Florence for support, wary of Siena’s growing interference. In Siena’s eyes, however, such behaviour smacked of “rebellion,” almost a personal slight. Florence’s political response took the form of sending a “supply convoy, escorted by tens of thousands of soldiers,”[1] to the banks of the Arbia—a clear message that Siena’s expansion to the south would not go unchecked.
Behind the scenes, the figure of Manfred – son of the late Emperor Frederick II of Swabia – was emerging, resolved to resist the papacy’s ambitions in his homeland: the Kingdom of Sicily, in southern Italy. In 1258, when false news spread that his four-year-old nephew Conradin of Swabia, the imperial heir, had died, Manfred seized the opportunity to be crowned in Palermo. This audacious move by the new King of Sicily swiftly provoked Pope Alexander IV’s furious backlash, accusing him of usurping the Throne of Saint Peter’s rights over those lands. Even so, the Swabian sought diplomatic solutions, keeping good relations with Guelph cities such as Genoa and Venice, and even tried to secure an accord with Florence, long in league with the papacy.
Manfred’s objective was clear: to cast himself as arbiter, or “balancing force” among the many Italian cities and factions, well aware of how volatile they were and poised for war. In 1259, he dispatched an embassy to Florence to isolate Pisa, forcing it into his network of alliances. But the negotiations fell through, and by then, anticipating conflict, Manfred of Sicily sent a first contingent of knights to Siena—small but symbolic—followed by larger units under his uncle Giordano d’Agliano. Siena swore loyalty in Frederick II’s name, though Manfred insisted on a clause specifying that the pact “is not directed against the Church”, as he was reluctant to break with the pope entirely. For its part, Siena worried that the king, in his quest for a broad peace, might sacrifice Sienese interests to benefit Florence or Lucca.
In this complicated chess match, Pisa ended up almost on the sidelines. Despite being a city of proven Ghibelline faith, it was excluded from Manfred and Siena’s designs. Florence, meanwhile, did not abandon its Guelph leanings, excommunication notwithstanding. The city remained determined to contain Swabian influence in Tuscany, confident it could still rely on a certain goodwill from Alexander IV, though relations with the pontiff were far from calm. By late 1259, the scene appeared almost frozen: Siena felt (in its own way) supported by Manfred, Florence prepared to mobilise against its rival, Pisa stood outside the major alliance framework, and Orvieto and Perugia were torn by internal Guelph or Ghibelline factions, each seeking some advantage.
A mood of growing confidence
Siena tried a shrewd diplomatic approach, negotiating with Ghibelline factions in Perugia and Orvieto, while Manfred’s troops advanced on Grosseto and Montemassi. In that tangle of interests and self-preservation, Manfred’s true aim seemed to be gathering the Aldobrandeschi counties under his sway—lords of the mountainous regions—making Siena a junior ally. Within Siena, meanwhile, the idea of a decisive showdown with Florence was spreading: an embassy to Manfred was planned to request more troops, yet the city also sent a friar to Alexander IV as a last-ditch attempt at mediation. It proved futile, as Florence was already blocking Sienese property in its territory and urging its own citizens to put aside internal feuds with war looming ever closer.
A mood of growing confidence took hold in Siena as conflict approached, vividly illustrated in a letter from 1260, written by a group of friends to a Sienese merchant living in France:
“When we write this letter, [our friends] Mino Pieri and Orrando Buonsignore are not in Siena, but with the forces heading towards Montepulciano […] Know, Iachomo, that these days we are busy and spending heavily, because of the war against Florence. And know that it will cost us dearly, but we shall deal with Florence so thoroughly that we won’t regret it […] we have already pillaged Colle and the lands near Montalcino […] Count Giordano d’Agliano has set out with all the German and Sienese knights and the town militia to sack Montepulciano, and to do so without ceasing […]. We cannot say what will happen next […] know this: eight hundred knights are stationed here in Siena to destroy and annihilate Florence. And know that they are all so afraid of us and our knights that they’re wetting themselves […] [the German knights] pursued them from hill to hill like criminals; they burned and pillaged as close as four miles from Florence. Now you can see why they fear us. And know that we shall do them great harm this year, if God wills […]
Monday, 5 July 1260”[2].
In the spring of 1260, tensions between Florence and Siena reached a boiling point, driving Tuscany towards a conflict that would reach one of its most dramatic peaks in the Battle of Montaperti.
Spurred on by increasing Sienese raids in the Maremma and Valdorcia regions, the city of the red lily began mobilising its own forces and allies. Decades later, Giovanni Villani recounted that Florence’s stated aim was to bring aid to Montalcino, a pro-Florentine stronghold rumoured to be on the verge of siege. Yet given the scale of the mobilisation, it appears they were gearing up for something far more extensive than a mere support mission.
A first Florentine victory…or not?
According to the chronicles, the first engagement took place on 18 May 1260, just outside Siena’s main northern gate, Porta Camollia – still visible today – though a short distance away, near Santa Petronilla. Unfortunately, once more we find conflicting accounts in the sources. Here is the Florentine version, as told by Giovanni Villani:
“During that siege, the [Ghibelline] exiles from Florence hosted a feast for the German knights [sent by King] Manfred [of Sicily]. Once they saw these knights inebriated [with wine], they urged them to arm themselves and mount their horses to attack the Florentine army, promising lavish gifts and double pay […] The Germans, frenzied and drunk, rode out from Siena and recklessly charged the Florentine camp, inflicting great losses despite being few [in number], as there were only a handful of guards […] But once they overcame the initial shock, [the Florentines] armed themselves and organised their defence; and not a single [enemy] who rode out from Siena returned alive. All were unhorsed and killed, and Manfred’s [Sicilian] standard was captured and dragged through the mud.”[3]
On the other hand, the Sienese version turned the story on its head: “[The German knights] launched a furious attack on the Florentine camp, [who] fled, suffering over two hundred dead and five hundred wounded.” According to Siena’s chroniclers, “in the end, the Florentines and their army returned to Florence for fear that more enemies might come out of Siena.”[4].
The discrepancy between these accounts indicates that the clash on 18 May was no mere skirmish, but a serious wake-up call. Indeed, over the following days, the Sienese Commune took care to treat the wounded German knights at the public’s expense and to summon further reinforcements from Manfredi. Florence, in turn, decided to raise an even larger army, determined not to be caught off guard.
Florence preparing for war
A most precious record of these preparations has survived to the present day: the Libro di Montaperti, among the most closely guarded treasures in the State Archives of Florence and personally seen by only a handful of scholars. Within its pages, we find lists of names, fines, authorisations for buying and selling horses, and an exhaustive set of rules on how and when one was expected to answer the call to arms. Every knight, infantryman, doctor, and notary knew exactly what their duties were, the minimum gear they were required to bring, and the penalties they would incur if they avoided serving. Let us look at the details together.
First of all, while the city summoned a general mobilisation, it never fielded its entire force at once. On each occasion, the captain of war chose three or five Sesti (districts of Florence) in rotation to send into the field, while the others remained behind to defend the city. Each Sesto divided its men under vexilla, further splitting them into bands of twenty-five (venticinquine) drawn from the various parishes.
Infantry
Notarial registers detail the equipment required: infantrymen wore a steel cervelliera (a light metal skullcap), a gorget to protect the neck, and either leather or padded fabric breastplates. They also had iron sleeves for their arms, a spear, and a wooden shield covered in leather. All costs fell to the individual citizen, and lacking even a single item could result in a steep fine – ranging from 10 soldi (for one missing piece) to 20 soldi (if someone turned up without armour). Considering that a foot soldier’s daily pay was 30 denari (about 2 soldi), a fine might be the equivalent of around 2.000 modern dollars.
Mounted troops
Cavalry, the noble core of the army, was organised into six or seven squads of 25 knights each, set out in five poste of five men apiece. Every knight was required to own a warhorse valued at no less than 45 lire, complete with saddle, covering, helm, iron hauberk, armoured leggings, lance, and shield. Given the high cost of horses, some hopeful warriors shared the same mount in joint ownership. There were, in fact, cases of individuals stating: “non habet nisi medietatem unius equi” (“he only holds half a horse”), forcing them to give up their place as cavalrymen and pass it on to a substitute.
Nonetheless, the army did not consist solely of infantry and knights. There were also the so-called equitatores—mounted fighters who were not necessarily noble—grouped into cinquantine (a group of 50 men) as well as the berrovieri, professional soldiers on fixed-term contracts, often from other cities (something akin to modern-day contractors). These experts also profited from the “prisoners market” whereby the Comune paid a sizeable bounty for each captive enemy. If the Comune deemed the cost too high, it left the prisoner in the captor’s hands, free to sell or ransom him. Such a system was hardly charitable, yet it effectively spurred the soldiers to give their utmost in battle.
Support troops, logistics and the Carroccio
Alongside the berrovieri, the Florentine Council also hired specialised captains. One Pietro di Bazacapa from Milan was contracted for himself and fifty men, on condition that he not include any Florentine criminals convicted of serious offences. Their monthly pay stood at eight florins per head (roughly 35 lire, equivalent to around 19.000 modern dollars), by no means a paltry sum. For crossbowmen and archers, the Commune appointed officials to recruit one marksman in every four individuals per parish, seeking out young, skilled archers. At the same time, they trained the pavesari, who carried large pavesi shields behind which crossbowmen could shelter in action.
The most symbolic element of the Florentine army was bound up with the carroccio, a war cart painted bright vermilion and fitted with two poles supporting the Comune’s banner—vital for identifying one’s “headquarters” amid the chaos of battle. It was drawn by two oxen in colourful harnesses, protected by dozens of milites and an infantry contingent assigned by Sesto. A proposal was also raised to recruit 200 sappers and 100 marraioli, tasked with levelling the ground and demolishing any enemy fortifications
14th century, ms. Chigi L VIII 296, Vatican Apostolic Library
On the logistical front, Florence required the countryside to supply large amounts of grain and other provisions. Moreover, to safeguard the city while its main army was away, a detailed defensive network was established, designed to stem any potential Sienese raids. Plans were made for a system of fire- or smoke-based signals to alert the authorities to an approaching foe: by night, the number of bonfires and the rate at which they were lit and extinguished indicated the size of the threat; by day, plumes of smoke served the same role.
Siena’s preparations
As summer drew near, the size of Florence’s army became truly imposing. A figure of 35,000 soldiers circulated[5], said to be ready to depart for Montalcino, believing they would either undertake a protracted siege or a pitched battle against Siena’s forces, themselves bolstered by the knights sent by Manfredi. This illustrates Florence’s recognition that it was at a real crossroads: either halt Siena’s expansion from the outset or risk Montepulciano and Montalcino falling irrevocably into the rival sphere, undermining the entire balance of Tuscany.
In the meantime, Siena did not stand idle. Its counteroffensive, calls for reinforcements, and the arrival of German knights all signalled that words were about to give way to deeds on that side as well. We have fewer precise sources for Siena, so we can only hypothesise based on parallels with other thirteenth-century troop musters.
Given the severity of the looming Florentine attack, there was no room in Siena for partial or rotational recruitment: the Commune summoned all milites and cavalcatores, meaning the fully armed nobility, young men not yet invested with the cingulus, and even commoners who could fight on horseback. Essentially, any man between the ages of sixteen and seventy.
Siena and its allies
Siena’s army did not match Florence in numbers. Sources from the spring mention some six hundred citizen cavalry, with additional horsemen from the countryside, German and Italian mercenaries, as well as a certain number of Florentine exiles—though these are hard to quantify. There was also a sizeable body of men sent by Manfredi: according to the chronicles, a first contingent of six hundred, led by Count Giordano d’Agliano (the same Count Giordano cited in the merchant’s letter), arrived in Siena at the end of 1259, with a second group of eight hundred knights coming a few months later. These figures, however, lack administrative records to confirm them and stem solely from accounts of varying reliability; it is likely the true benefit of such outside allies was less than later Florentine sources would claim, in their bid to explain defeat by citing massive German aid.
Sienese cavalry and infantry
For their part, the Sienese infantry was organised – like the cavalry – according to their Terzi, then split into formations of fifty men (the so-called “cinquantine”). Unlike what would be said in later periods, there was as yet no “military company” system in Siena around 1260. In the era of Montaperti, one heard instead of “società delle armi” formations that might well include professional soldiers from diverse backgrounds. We do not know precisely what role they played in Siena’s frantic preparations that summer, but in any event, the city called on all its resources, fearing Florence might raze it to the ground with the power of its large army.
It is even more difficult to gauge possible reinforcements from Sienese territories or allied cities. In the communal wars, it was standard practice to leave garrisons in border strongholds rather than gather every soldier into a single field force. Thus, at least some men from the most vulnerable fortresses (particularly in Chianti or the Maremma) remained at their posts, shielding against Florentine incursions. Similarly, contingents dispatched from nominally allied locations like Cortona were never definitively counted. Later chronicles also passed down the legend of Saracen archers from Lucera and “schismatic Greeks” coming to Siena’s aid, a topic appearing in Guelph propaganda and in some narratives composed decades or even centuries later. These rumours stemmed from the fact that Manfredi, in other circumstances (for instance, during the 1264 campaign around Rome), did indeed field some Muslim archers. Yet there is no confirmation of their presence at Montaperti in any administrative or near-contemporary accounts of the battle. The sole reference to a force made up of “non modica Sarracenorum, Grecorum, Germanorum et regnicularum militum” (“a not insignificant group of Saracens, Greeks, Germans and soldiers from those small kingdoms”) appears in a letter the Florentine Guelphs addressed to Emperor Conradin, aiming to secure his intervention. It may have been a rhetorical exaggeration designed to paint the invasion as an almost “infidel” menace.
The legendary Carroccio of Montaperti, and the Sienese commanders
Although there are no records akin to Florence’s, we know that Siena deployed its own carroccio: a war cart bearing a great white banner, a symbol of enormous moral weight, no different to the Florentine version and destined to figure in the epic accounts of the looming battle.
As for commanders in the field, later historians relished embellishing stories of supposed “general captains” or feudal noblemen acting as strategists. Yet the most likely candidate for coordinating Sienese forces was Francesco Troisio, the city’s podestà and a trusted associate of King Manfredi of Sicily. Giordano d’Agliano, for his part, oversaw broader strategy, wielding the authority bestowed by the Swabian monarch.
Before Montaperti
Thus, two massive forces emerged, 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.
During those months, the Florentines believed they had a genuine chance of success, despite conflicting signals coming from the field. And so, with these forces, these recruitment contracts, and the constant clang of weaponry being readied, the army finally set out towards late summer, crossing the boundaries of Florence’s territory and marching resolutely into the Valdorcia. The decisive encounter was now only a short way off, and the stir of these preparations would soon give way to action: the confrontation that went down in history as the Battle of Montaperti.
Bibliography
- Anonymous. (1260, July 5).Lettera di Iacomo, Giovanni, Vincenti e altri compagni da Siena a Iachomo Guidi Chaciaconti, in Francia . In Paoli, C. (Ed.), Lettere volgari del secolo XIII scritte da senesi (pp. 13–24). Gaetano Romagnoli.
- Balestracci, D. (2019). La battaglia di Montaperti. Editori Laterza.
- Montauri, P. di T. (Attributed). (n.d.). Cronaca senese. As cited in Balestracci, D. (2019, p. 72).
- Paolo di Tommaso Montauri (Attributed). (n.d.). Cronaca senese..
- Pispisa. (n.d.). Il Regno di Manfredi (p. 11). As cited in Balestracci, D. (2019, p. 35).
- Villani, G. (1991). Nuova Cronica (G. Porta, Ed.). Fondazione Pietro Bembo/Guanda.
[1] All the information about the conflict between Siena and Florence until the third quarter of the 13th century is based on the wonderful works of Prof. Duccio Balestracci, which currently represent the state of the art on this subject. Therefore, unless otherwise specified, please refer to Balestracci D., La battaglia di Montaperti, Editori Laterza, 2019
[2] “[…] Mino Pieri […] Orrando Buonsignore non era a Siena, quando chesta lettera si scrisse, anzi era ne l’oste a Montepulciano […] sapi, Iachomo, [che] noi semo ogi in grande dispesa et in grande facenda, a chagione de la guer[ra] che noi avemo con Fiorenza. E sapi che a noi chostarà asai a la borsa; ma Fiorenza chonciaremo n[noi] sì, che giamai no ce ne miraremo drieto […] noi avemo guasto tutto Cholle e Montalcino intorno, e a Montepulciano andamo per gustare […] si partì el chonte Giordano chon tuti i chavaieri tedesci e senesi e col terziero di Cità, e andò là per guastarlo, e guastalo onnie dì […]. Che si sarà per innanzi, noi no sapemo […] E sapi che ne la cità di Siena sono posti ottochento chavali per dare morte e distruggimento a Fiorenza. E sapi ch’elino àno si grande paura di noi e de’ nostri chavaieri, ch’elino si sconpiscano tutti […] [i cavalieri tedeschi] andavanli chaciando d’in pogio in pogio chome gativi; e andaro ardendo e abrusciando insino apresso a Fiorenza a quatro miglia. O puoi vedere, s’elino ne dotano e avonne paura di noi. E sapi che noi a loro daremo el malano unguanno in chesto anno, se Dio piace […] lunidì, cinque dì intrante lullio [1260]”
Lettera di Iacomo, Giovanni, Vincenti e altri compagni da Siena a Iachomo Guidi Chaciaconti, in Francia. Menzionata in Paoli C., Lettere volgari del secolo XIII scritte da senesi, p. 13-24, Gaetano Romagnoli, Bologna, 1871
[3]“Avenne in quello assedio che gli usciti di Firenze uno giorno diedono mangiare a’ Tedeschi di Manfredi, e fattigli bene avinazzare e innebbriare, a romore caldamente gli feciono armare e montare a cavallo per fargli assalire l’oste de’ Fiorentini, promettendo loro grandi doni e paga doppia […] I Tedeschi forsennati e caldi di vino uscirono fuori di Siena, e vigorosamente assaliro il campo de’ Fiorentini, e perch’erano improvisi e con poca guardia, avendo la forza de’ nemici per niente, con tutto che’ Tedeschi fossono poca gente, in quello assalto feciono all’oste grande danno […] Ma alla fine ravveggendosi, presono l’arme e la difenza contra i Tedeschi; e di quanti n’uscirono di Siena non ne scampò niuno vivo, che tutti furono morti e abbattuti, e la ’nsegna di Manfredi presa e strascinata per lo campo”
Villani G., Nuova Cronica, VII, 75, menzionato in Balestracci D., La battaglia di Montaperti , p.72, Editori Laterza, 2019
[4] “Asaltarono vigorosamente el campo de’ Fiorentini [i quali]… si misero in fuga e fune morti più di 200 e feriti da 500”; “e’ Fiorentini co’ loro oste si ritornonno a Fiorenza per paura che di Siena non uscisse più gente”
Paolo M., Cronaca senese conosciuta sotto il nome di Paolo di Tommaso Montauri
[5] The exact amount of forces deployed is not known to us – and is, to be honest, irrelevant. There is a general tendency in ancient sources to provide exorbitant figures to exaggerate the size of armies, especially in those (like the Sienese Tommaso Montarui, or the Florentine Giovanni Villani), who write about events that occurred decades earlier. In short, it is not known exactly how many there were, except that they were indeed a lot.
