There is no evidence that Niccolo Machiavelli ever met the charismatic Dominican friar and fiery preacher, Girolamo Savonarola, but we know he attended at least one of the friar’s sermons. In a letter to Ricciardo Bechi, dated March 9, 1498, Machiavelli described his experience. He was not impressed. He wrote that, in his judgement, Savonarola was a hypocrite who,

…acts in accordance with the times and colors his lies accordingly.*

Savonarola played a seminal role in the development of Machiavelli’s political and moral thought; not only through what Machiavelli perceived of him, but in the way Savonarola organized the government of Florence during his leadership.

Savonarola had been well schooled in both biblical and classical studies. He spent his early years as an itinerant priest making fiery and contentious sermons calling for reform and repentance, with an apocalyptic theme, throughout the northern Italian city states. After several years, in 1490, he was assigned to the convent of San Marco, where Lorenzo de Medici (Lorenzo the Magnificent) met him, and decided to make him spiritual counsel for his family.

In Florence, his sermons against what he saw as tyranny and corruption grew increasingly strident, and Savonarola peppered them with prophesies about apocalyptic disasters, and Florence rising to become the “new Jerusalem.” Wikipedia notes,

In 1492 Savonarola warned of “the Sword of the Lord over the earth quickly and soon” and envisioned terrible tribulations to Rome. Around 1493 (these sermons have not survived) he began to prophesy that a New Cyrus was coming over the mountains to begin the renewal of the Church.

When the French king, Charles VII rode his army into northern Italy, in 1494, many of Savonarola’s followers believed it was proof of this prophesy. As Charles’ army pushed through Italy, defeating one opponent after another, and sacking cities along the way in order to get to the Kingdom of Naples, more and more Florentines turned to Savonarola for help to prevent their city suffering a similar fate.

By this time, Lorenzo had died (1492). His son, Piero – called Piero the Unfortunate – took over as the city’s ruler and proved inadequate to the role. Piero dithered, attempted to get Charles to bypass Florence, and treat the city as neutral. Charles would have none of it, and threatened to capture and raze the city. Florentines, desperate to protect their city and their lives, defected to Charles’s side; many flocked to Savonarola to protect them.

Piero lost his nerve. He surrendered Florence to Charles, caving in to every demand and not even attempting to negotiate better terms. In response, the populace rose up and looted the Medici home. In December, 1494, Piero and his family fled (he would eventually ally with the French, and lose his life after a battle in which the French lost). The populace turned to the fanatical friar to help them negotiate with the French, and then establish a new government. He did so with gusto.

Savonarola played on the emotions and envy of the Florentines. He convinced them that they were being abused by the rich; their opulence was a clear sign of their tyranny.

Machiavelli was, at this time, 25. He would later write that people followed Savonarola indiscriminately, and believed his every word without any proof:

And though it be easier to impose new institutions or a new faith on rude and simple men, it is not therefore impossible to persuade their adoption by men who are civilized, and who do not think themselves rude. The people of Florence do not esteem themselves rude or ignorant, and yet were persuaded by the Friar Girolamo Savonarola that he spoke with God. Whether in this he said truth or no, I take not on me to pronounce, since of so great a man we must speak with reverence; but this I do say, that very many believed him without having witnessed anything extraordinary to warrant their belief; his life, his doctrines, the matter whereof he treated, being sufficient to enlist their faith.
The Discourses, 1, XI.

As a cleric, Savonarola could not hold office. However, he formed a political party from his followers, the Frateschi, and together they set about to remake Florence in Savonarola’s pious, Christian, and somewhat egalitarian model. Not all of this was bad. They wrote a new constitution that gave the vote to the artisan class, not merely the nobles. They created an election process to appoint citizens to some civic offices not simply hand out offices like favours. They passed a “Law of Appeal” to limit rulers and their supporters from using exile and capital punishment as “factional weapons.”

But making laws that seemed to offer more liberty was not enough. They had to be kept, and not all were. This would cause Savonarola a loss of face and support. Machiavelli later wrote,

After the year 1494, the city of Florence reformed its government with the help of the Friar Girolamo Savonarola… Among other ordinances for the safety of the citizens, he caused a law to be passed, allowing an appeal to the people from the sentences pronounced by “the Eight” and by the “Signory” in trials for State offences; a law he had long contended for, and carried at last with great difficulty. It so happened that a very short time after it was passed, five citizens were condemned to death by the “Signory” for State offences, and that when they sought to appeal to the people they were not permitted to do so, and the law was violated. This, more than any other mischance, helped to lessen the credit of the Friar; since if his law of appeal was salutary, he should have caused it to be observed; if useless, he ought not to have promoted it. And his inconsistency was the more remarked, because in all the sermons which he preached after the law was broken, he never either blamed or excused the person who had broken it, as though unwilling to condemn, while unable to justify what suited his purposes. This, as betraying the ambitious and partial turn of his mind, took from his reputation and exposed him to much obloquy.
The Discourses, Book 1, LVI

Savonarola continued preaching, and making more of his alleged ability of prophesy. With 20-20 hindsight, he publicly claimed he had predicted the deaths of Lorenzo de’ Medici and Pope Innocent VIII, and the invasion of King Charles of France, . He spoke about his visits to heaven where the Virgin Mary revealed the future to him. He told his audience that “God had chosen Florence,” and promised that, if the people of Florence followed his teachings, “it would have riches, glory and power.”

He also called on Florentines to live pure lives and rid their city of “vice”. His party passed new laws against ‘sodomy’ (which included male and female same sex relations), adultery, public drunkenness, and other “moral transgressions.” Gangs of fundamentalist-minded boys and young men  – pious thugs – patrolled the streets, attacking anyone whose dress or behaviour they considered “immodest.” The people followed his “puritanical” lifestyle eagerly – at first. Savonarola’s constraints to show signs of wear fairly soon. By 1497, the bars were selling wine and spirits again.

The peak of Savonarola’s civic madness came in February, 1497, when he organized the Bonfire of the Vanities where he built a large bonfire in the main square and exhorted Florentines to cast into it any “objects that are deemed to be occasions of sin.” His roving gangs helped round up material from the residents, often forcibly. Thousands of cosmetics, pieces of priceless art, books, sculpture, painting and furniture were destroyed.

Pope Alexander VI initially tolerated fra Girolamo’s somewhat erratic actions, and even ignored the friar’s increasingly strident and accusatory attacks on the church and the papacy. Florence refused to join the pope’s Holy League alliance to drive out the French, because Savonarola and his party already had an alliance with the French to protect them from both the papal ambitions and the threatened return of the Medici. Although the French never provided the promised help, Savonarola clung stubbornly to their side.

The pope had had enough. He started an exchange of angry letters with Savonarola. The friar in turn sent the pope his “Compendium of Revelations,” a self-serving account of his “prophetic career.”

The exasperated pope demanded Savonarola appear in Rome. The friar pleaded ill health, so the pope banned him from preaching. Savonarola obeyed for a short while, but couldn’t keep his mouth shut for very long. He resumed his sermons, in an even more challenging and castigating manner. So the pope used his last weapon: excommunication, in May, 1497. he also threatened the Florentines with “interdiction” if they continued to offer him sanctuary in their city.

For the next ten months, Savonarola ignored the order, and continued to preach. He became increasingly convinced of his divine mission and spoke of performing miracles to prove himself. In March, 1498, Machiavelli heard one of his sermons at San Marco. In his letter, he wrote that the friar’s words had an effect on those in the crowd who didn’t examine them closely or apply critical thinking to them, but that they were meant mostly to bolster the faith of the followers while denigrating any perceived opponents:

Now that our friar was in his own house, if you had heard with what boldness he began preaching and with how much he continued, it would be an object of no little  admiration. Because, fearing greatly for himself and believing that the new Signoria would not be reluctant to injure him – and having decided that quite a few citizens  should be brought down with him – he started in with great scenes of horror; with explanations that were quite effective to those not examining them closely, he pointed out that his adherents were excellent people while his opponents were most villainous, and he drew on every expression that might weaken his opponents’ party and fortify his own.

The government of Florence, under increasing political, economic, and religious pressure, tried to convince Savonarola to shut up. Many followers left his side, others faltered as pressures mounted and the city’s economic status wilted. In a final, desperate attempt to regain his lost authority, Savonarola accepted a challenge by a Franciscan preacher, who proposed he and Savonarola walk through fire to prove who had the most favour with God.

The date for the ordeal was April 7, 1498, in the central square. When the day arrived, a huge crowd attended. The two priests and their followers milled about nervously as the flames grew. They each, separately, found one excuse after another to delay the test. Hours later, a heavy spring rain drenched the fires, and in frustration, government officials cancelled the contest.

The crowd was not pleased. The people had put their faith in Savonarola, and believed his words. He lacked the faith he demanded they themselves show. When he failed to follow through, they blamed him for the fiasco, and for the low esteem in which Florence had fallen with other rulers and states, since his arrival. A mob assaulted the convent of San Marco where he was headquartered.

Savonarola and two of his fellow monks, Fra Domenico and Fra Silvestro Maruffi, were arrested and imprisoned. They were tortured; Savonarola confessed to “having invented his prophecies and visions.” He then retracted his confession, was tortured more, and confessed again. On May 23, 1498, the three were publicly condemned as heretics and schismatics. They were hung in the public square, and their bodies burned.

Savonarola’s fall from grace, and his death had several aftereffects. His words would not be forgotten, and would later influence many others who felt that the papacy had grown too corrupt and concerned with temporal power – Martin Luther, the architect of the Reformation a few years later, would read them and praise the friar. The Huguenots in France would take some of their reforming inspiration from him.  Even as late as the mid-20th century, Savonarola  would be held up as an early model for social justice and reform, so much so that – despite his intolerance and authoritarianism – he has been considered for sainthood.

For Florence, the major shift was the creation of the republic after the friar, that would soon hire young Niccolo Machiavelli as an official – a republic that was founded on many of the principles and bureaucratic systems Savonarola initiated.

For Machiavelli, Savonarola would be a complex lesson. He appears as the “unarmed prophet” who failed because he lacked the force necessary to secure his authority:

“If Moses, Cyrus, Theseus, and Romulus had been unarmed they could not have enforced their constitutions for long — as happened in our time to Fra Girolamo Savonarola, who was ruined with his new order of things immediately the multitude believed in him no longer, and he had no means of keeping steadfast those who believed or of making the unbelievers to believe.”
The Prince, VI

Machiavelli would also contrast Savonarola’s rule with that of Piero Soderini’s, later, arguing that Savonarola was unable to deal with adversaries effectively, and did not have the followers to carry out the necessary tasks for him:

But when fortune is not thus propitious to him, he must contrive other means to rid himself of rivals, and must do so successfully before he can accomplish anything. Any one who reads with intelligence the lessons of Holy Writ, will remember how Moses, to give effect to his laws and ordinances, was constrained to put to death an endless number of those who out of mere envy withstood his designs. The necessity of this course was well understood by the Friar Girolamo Savonarola, and by the Gonfalonier Piero Soderini. But the former could not comply with it, because, as a friar, he himself lacked the needful authority; while those of his followers who might have exercised that authority, did not rightly comprehend his teaching. This, however, was no fault of his; for his sermons are full of invectives and attacks against “the wise of this world ,”that being the name he gave to envious rivals and to all who opposed his reforms.
The Discourses, Book 3, XXX

On the other hand, Machiavelli argued for Florence to retain some of the institutions – such as the election for public office – that Savonarola and his Frateschi had initiated. A republican at heart, Machiavelli valued the change from the hereditary state under the Medicis to a more inclusive government that allowed him a chance to prove his worth.

Savonarola’s rise and fall was also a lesson in the potentially disastrous intersection of religion and politics, as well as the practical need to have more than faith to support your goals. Machiavelli’s own views on the role of the papacy and its involvement in temporal and political matters would be shaped in part of Savonarola’s ideals. As Wikisource.org notes, Machiavelli shared some of Savonarola’s sentiments:

When it comes to religion Machiavelli is not the cold time-server that some would have people believe. Echoing Savonarola, he complains how the Christian religion had decayed from “its principles,” coming close, “without any doubt, to ruin or punishment.” The common belief that Machiavelli considers Christianity to be inferior to the classical religions is not founded. With great care, he makes a distinction between original Christianity and the corrupted one of his times. He says: “If from the beginning of the Christian republics the Christian religion would have maintained itself according to its giver’s order, the Christian state and republic would have been more united and happy that they are presently.”
(Quotes from The Discourses, Book 1, XII)

A few months before Savonarola was overthrown and executed in the main square, in 1498, Machiavelli stood in the election for a position in public office. He lost, possibly because he was known to be critical of Savonarola. But in April, the Frateschi’s political leader, Francesco Valori, was murdered, and the government started to unravel. Many of Savonarola’s supporters, including chancery staff, were removed from office by the anti-Savonarola newcomers.

Machiavelli ran again for office after Savonarola had been executed. This time he won. At age 29 he became secretary of the Second Chancery; an executive position in the department that kept the ruling council informed on military and political affairs. Without the new rules Savonarola had put in place, he would not likely have been given such a position. Who knows if he would have ever penned his famous works, if not.
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* A somewhat different translation can be found in The Letters of Machiavelli, translated by Allan Gilbert, University of Chicago Press, USA, 1961. Gilbert translates: “Thus, according to my judgment, he keeps on working with the times and making his lies plausible.”