In the final chapter of his famous book The Prince (written in c. 1513, first printed in 1532) Niccolò Machiavelli gloomily evoked a contemporary Italy ‘more enslaved than the Hebrews, more servile than the Persians, more dispersed than the Athenians, without a head, without order, beaten despoiled, torn, pillaged, and having endured ruin of every sort.’ There may in the past, he wrote, have been men who thought themselves ordered by God to save Italy but they had been knocked back by fortune. Therefore, he continued, ‘left as if lifeless, she [i.e. Italy] awaits whoever it can be that will heal her wounds, and put an end to the sacking of Lombardy, to the taxes on the kingdom [of Naples] and on Tuscany, and cure her of the sores that have festered now for a long time. One may see how she prays God to send her someone to redeem her from these barbarous cruelties and insults.
This female personification of Italy was not uncommon after two decades of French, German, Spanish and Swiss incursions into the peninsula (see, for example, the image of the 1513 medallion depicting a personified Italy assaulted by French fury which accompanies this post). It is an image that would certainly have reminded many readers forcefully of the rape of women by soldiers that always accompanied military conquest and the festering sores of syphilis which spread with the armies and was therefore called the French pox by Italians. Finally, this passage would also have brought to mind the massacres of civilians that could occur in the course of the sacking of Italian cities and the passage of troops.
In the same section of The Prince Machiavelli then seemed to offer some glimmer of hope for salvation. He addressed the Medici dedicatee of the work directly, claiming: ‘Nor may one see at present anyone in whom she can hope more than in your illustrious house, which with its fortune and virtue, supported by God and by the Church of which it is now prince [following the election of Pope Leo X Medici in 1513], can put itself at the head of this redemption.’ In fact, he wrote, God seemed now to favour them as much as He once favoured Moses, Cyrus and Theseus – the leaders who saved the Hebrews, Persians and Athenians. There is ‘great justice’ in the cause, he continued, and he quoted Livy to the effect that “for war is just to whom it is necessary, and arms are pious when there is no hope but in arms”. Moreover, he claimed that ‘extraordinary things without example’ had now been brought about by God: ‘the sea has opened; a cloud has escorted you along the way; the stone has poured forth water; here manna has rained; everything has concurred in your greatness.’
These are exalted words indeed; the reality was rather less glorious. In fact, the ‘fortune’ of the Medici family was intimately connected with the bloody and inglorious sack of Prato by the Spanish forces of the Holy League which occurred at the end of August 1512, only a few months before Machiavelli wrote these words. The sack was a political disaster for the pro-French Soderini regime in Florence, which failed to defend the city from the Spanish troops and thereby helped to bring about the return of the Medici to rule after sixteen years of exile. Cardinal Giovanni de’ Medici (later Leo X) wrote coolly to Pope Julius II, the bellicose head of the League, about how the Spanish had assaulted Prato with valour and had put the place to sack ‘not without some cruelty in killing, which was the least that could be done … The capture of Prato in such a sudden and cruel way, although it has displeased me, yet will have brought this benefit as an example and a terror to others.’ By contrast, the sack was a personal disaster for Machiavelli. He had been intimately connected with organisation of military affairs in Florence during the previous decade and the return of the Medici helped to force him out of office and into exile.
Given the personal and political humiliation represented by the sack of Prato and prompted by Erica Benner’s recent new reading of The Prince it is tempting to read as ironic Machiavelli’s heady evocation of the providential ‘fortune and virtue’ of the Medici immediately after an account of the ‘barbarous cruelties and insults’ suffered by Italy and in which the Medici played no small part. The reaction of the Florentine Bartolomeo Cerretani to the sack is perhaps instructive here; it provides a sense of the providential interpretation that the incident could provoke among Medici partisans. Cerretani provided an unusually emotional account of the sack and massacre at Prato at the end of his Storia Fiorentina (c. 1512):
And because Death you solicit me to mind at this point to gorge on the dead, and because you raging woman called Cruelty by mortals I see you first to enter into the wretched land to bathe, feast, and thrust yourself at your pleasure in this horrible day in the miserable blood of humanity, yet to satisfy you I have taken the pen with a trembling hand, with eyes filled with tears, with a mind surrounded by fear, with a heart in terror and amazement writing that the bright sun at such an hour covers its shining face and the tumultuous enemy ranks with unheard of fury enter hungry for the blood of plunder and supplies, men of Granada, circumcised marranos, and Jews.
Cerretani described how even those who were unable to escape, threw down their arms, and kneeled with their arms crossed in mercy before the attackers were cruelly cut to pieces. The great church of Prato called the Pieve sheltered two hundred behind locked doors, and when the enemy entered they attacked a crucifix, killing the person who held it and lopping off one of Christ’s arms before massacring everyone and leaving a pool of blood to spread over the pavement. Similarly, every person who sought refuge in the church of the Vergine was killed, both women and the husbands and sons whom they embraced, as well in San Domenico, Sant’ Agostino, and other holy places. Cerretani went on to point out that in the rape of women and girls the soldiers of Italy and the Tuscans were more wicked and full of every vice than those of Granada. In a few hours more than 4500 men died, with a few survivors including those protected in a secure part of the palace of the Medici legate or in the palace of Giuliano and Giulio de’Medici. His account dwelled on the inhumanity of the sack: ‘And if I have had to tell of the inhumanity and unheard of cruelty they would make you believe that the earth would open itself up in pity.’
In stark contrast, Machiavelli’s surviving references to the sack of Prato involve a cool calculation of the weakness of the Florentine state. In a letter he possibly addressed to Isabella d’Este in Mantua, Machiavelli focused on the internal weakness of the Soderini regime much more than on any Medici ‘fortune’ or virtue’, or supposed providential purpose:[N]ews of Prato’s capture arrived and of how the Spaniards, having broken through some of the walls, began to force the defenders back and to terrify them. So that, after slight resistance, they all fled and the Spaniards took possession of the city, put it to sack, and massacred the city’s population in a pitiable spectacle of calamity. In order to spare Your Ladyship cause for worry in your spirit, I shall not report on the details. I shall merely say that better than four thousand died; the remainder were captured and, through various means, were obliged to pay ransom. Nor did they spare the virgins cloistered in holy sites, which were all filled with acts of rape and pillage.
In his description of the causes and effects of the sack here, Machiavelli avowed that he ‘did not want to interpolate any of those matters that might offend … as being lamentable and redundant.’ His letter may have been solicited by his unnamed noble correspondent through the offices of Giuliano de’ Medici himself and this may explain why it is largely concerned with the sack as a key moment in the Holy League’s attempt to oust the pro-French Soderini regime and install the Medici in power following their prolonged absence.
In particular, Machiavelli did not fail to analyse the actions of his erstwhile employer, the gonfalonier Piero Soderini who had been determined to strengthen his position in Florence with regard to the Medici and therefore followed military advice to entrench the main body of the republic’s defending forces in Florence rather than Prato. He had likewise rejected the viceroy’s demand for his resignation so that a gonfalonier favourable to the League could be appointed. Soderini, as Machiavelli points out, also overestimated the weakness of the enemy and refused to pay the sum of money demanded by the commander of the League forces as they menaced Prato. As a consequence, the city was sacked and troops who had been left behind as a garrison displayed only ‘cowardice’ under assault. Terrified by this display of power the Florentines finally ousted Soderini and the Medici, styled by Machiavelli as his ‘patroni’ and as the noble addressee’s ‘amici’, returned to power.
In his Discourses (c. 1513-17) Machiavelli developed this analysis and cited the sack of Prato as an example of a moment when Florence was ‘disordered’ by ‘necessity’, when the ‘modes’ of politics failed to allow for popular discontent, and when the people’s pride in rejecting a Spanish accord and in following the French party led to disaster. In the Art of War (c. 1519-20, first printed in 1521) Machiavelli also used the examples of sacks of cities during the Italian Wars to make a broader point about the weakness of Italian powers but, intriguingly, he omitted any reference to Prato. This omission deserves closer attention.
In the course of the dialogue, which unusually in Machiavelli’s output provides the Art of War with its structure, the figure of Fabrizio Colonna, an experienced condottiero or mercenary soldier, responds to a question about the cause for the modern neglect of military training. He argues that excellent captains have arisen in Europe when there were many competing rulers or empires that favoured virtue by necessity or by some other passion. This was the case in ancient times until Rome conquered the world and became the sole source of virtue. When Rome was corrupted a more virtuous people was able to prey upon it, but even when the empire was broken up by the barbarians this virtue was not reborn. One reason for this is that ‘today’s mode of living, on account of [lit. ‘with respect to’] the Christian religion, does not impose that necessity to defend oneself that there was in antiquity. For then men conquered in war were either killed or remained in perpetual slavery, where they led their lives miserably. Their conquered towns were either dissolved or, their goods taken, the inhabitants were driven out and sent dispersed throughout the world. So those overcome in war suffered every last misery.’ As a consequence, military excellence was maintained and honoured.
By contrast in the present day, Colonna says, because men only fear brief imprisonment and ransom in war, while rebellious cities are not demolished, men do not wish to submit to military orders and have little to fear, while weak cities defend themselves by siding with one or other of the unified powers who are victorious, while the rest live without fear of ‘ultimate ruin.’ Colonna’s response to the objection that since 1494 many towns have been put to sack and kingdoms lost, which should teach men to recover the ancient orders, is surprising. He says:
It is as you say; but if you note which towns have been put to sack, you will find that they are not the heads of states but among their members, as one sees that Tortona was sacked and not Milan, Capua and not Naples, Brescia and not Venice, Ravenna and not Rome. These examples do not make whoever governs change their presupposition. Indeed, it makes them stay more in their opinion of being able to buy themselves back with ransoms; and because of this they do not want to undergo the exertions of the training for war, since, on the one hand, it seems to them unnecessary and, on the other hand, a tangle they do not understand.
Those others, whom he deems ‘servants’, should be afraid but have no power to remedy matters, while the governments of Milan, Naples, Venice, and Rome (the ‘latter princes’) have either lost their states and cannot remedy the problem, or prefer to ‘remain without any hardship by fortune and not by their own virtue’, allowing fortune to govern them who are so weak in virtue.
Prato’s omission in the list of sacked cities is curious given that it represented one of those sacked towns that were ‘members’ rather than ‘heads of states’. Perhaps it was omitted because Machiavelli wished to imply that the Medici regime which returned in its wake in 1512 had in fact learned the hard lessons of war – a conclusion supported by the ostentatious praise he directs their way in The Prince. Or perhaps Prato’s shadowy presence was implied by the setting of the dialogue, in the shade of the Rucellai gardens which were located by the Florentine gate that led to Prato. With this omission was Machiavelli simply tactful by necessity in a book published in Florence during his lifetime – one of the few of his works to appear in this way? Or did Machiavelli believe that the Florentines, and indeed Italians generally, might learn the lesson of that sack and renew their modes with a political settlement that encouraged greatness and virtue? Certainly, it is worth noting that in 1521, when the work was published, the Medici were inviting suggestions for the organisation of Florentine government from Machiavelli and others, while a papal-imperial alliance seemed poised to drive the French out of Italy for good. Perhaps, like Chinese premier Zhou Enlai on the effects of the French revolution, Machiavelli was hinting that it was still ‘too early to say’ what the outcome of 1512 would be for Florence, or indeed for Italy.
 Machiavelli, Prince, 102 (Ch. 26). The unnamed men ‘ordered by God’ may be identified with Cesare Borgia of Girolamo Savonarola: Benner, Machiavelli’s Prince, 307.
 Machiavelli, Prince, 102-3 (Ch. 26).
 ‘Hanno messo la terra a sacco non senza qualche crudelità de occisione, de la quale non si è possuto far meno … La presa di Prato così subita et cruda, quantunque io ne habbia preso dispiacere, pure harà portato seco questo bene che sarà exemplo et terrore a li altri.’ Summary of letter dated near Prato, 29 August 1512, in Sanudo, Diarii, 15: 29.
 Bayley, War, 276-84.
 For an ironic reading of this chapter see Benner, Machiavelli’s Prince, 305-12.
 ‘E perché tu mortte mi solleciti al volere im questo puntto satiartti di mortti, e tu donna eferata da’ mortali chiamata crudelttà ti vegho la prima a entrare nella meschina terra per bagnartti e satiartti et fichartti a tuo piacere in questo horrendo g[i]orno nel misero sanghue humano, e però per contentarvi ho preso la penna colla tremantte mano cogl’ochi pieni di lacrime colla mente circunvolta nel timore col core terrefatto et sbighotito schrivendo che il sole chiaro in tale ora si coperse la lucida faccia e la nimica schiera tumultuosa con inaldita furia entrò dentro afamati di sanghue di roba et di vituaglie, homini di Granata marrani circuncisi et g[i]udei.’ Cerretani, Storia, 440. On the lessons of Prato see idem, Dialogo, 28-33, 36-7.
 Idem, Storia, 440.
 ‘Et s’io havessi a ddire le inhumanità et inaldite crudeltà vi si fec[i]ono chredo che la terra per pieta s’aprirebbe.’ Ibid., 441. Compare idem, Ricordi, 278-9.
 Atkinson and Sices, Machiavelli, 214-17 (quotation at 215-16); Machiavelli, Opere, ed. Gaeta, 354-60 (passage quoted at 357).
 Atkinson and Sices, Machiavelli, 217; Machiavelli, Opere, ed. Gaeta, 360.
 Richardson, ‘Lettera’.
 Atkinson and Sices, Machiavelli, 216.
 Ibid., 214; Machiavelli, Opere, ed. Gaeta, 354.
 Machiavelli, Discourses, 11, 25, 120, 194 (1.2.1; 1.7.4; 1.59.1; 2.27.3).
 Machiavelli, Art, 58-61 (2.284-316).
 Machiavelli, Art, xvi, 8 (1.8).
Atkinson, James B. and David Sices (trans. and ed.) Machiavelli and his Friends: Their Personal Correspondence. DeKalb: Northern Illinois University Press, 1996
Cerretani, Bartolomeo. Ricordi. Ed. Giuliana Berti. Florence: Leo S. Olschki, 1993
— Storia Fiorentina. Ed. Giuliana Berti. Florence: Leo S. Olschki, 1994
— Dialogo della mutatione di Firenze. Ed. Giuliana Bert. Florence: Leo S. Olschki, 1993
Machiavelli, Niccolò. Arte della Guerra, scritti politici minori, ed. Jean-Jacques Marchand, Denis Fachard, and Giorgio Masi. Rome: Salerno, 2001
— The Art of War, ed. and trans. Christopher Lynch. Chicago: University of Chicago Press, 2003
— Discourses on Livy. Trans. Harvey C. Mansfield and Nathan Tarcov. Chicago: University of Chicago Press, 1996
— Opere. Vol. 3. Lettere. Ed. Franco Gaeta. Turin: Unione Tipografico-Editrice Torinese, 1984
— The Prince, trans. Harvey C. Mansfield. Chicago: Chicago University Press, 1985
Bayley, C. C. War and Society in Renaissance Florence: The De Militia of Leonardo Bruni. Toronto: University of Toronto Press, 1961
Benner, Erica. Machiavelli’s Prince; A New Reading. Oxford: Oxford University Press, 2013
Richardson, Brian. ‘La Lettera a una gentildonna del Machiavelli.’ La Bibliofilia 84 (1982): 271-6