Niccolo Machiavelli‘s exile from Florentine politics — and subsequent entry into the intellectual canon — was cinched this date in 1513 when two of his friends (or possibly co-conspirators) were executed for a plot against the Medici.

Before he was an adjective, Machiavelli was a powerful minister of state for the Florentine Republic — the polity ensuing the 1498 execution of Savonarola.

Days after that stern friar burned to ashes on the Piazza della Signoria, Machiavelli was named the secondo segretario fiorentino,* alongside a primo segretario counterpart, the older and more cautious Marcello Virgilio Adriani.

What a moment this was to be a Florentine! The mighty Medici had been chased out of Florence and with the fall of Savonarola and his grim morals police the humanist dream of a classical republic suddenly seemed within grasp.

Machiavelli was just 29 years old when he reached this office, bursting with a patriot’s reckless exuberance — and a virile young man’s hedonism. He delighted in whores and in boozing around with his Chancery cronies Agostino Vespucci** and Biagio Buonaccorsi.

The correspondence of these indiscreet young Turks fill with profane and cutting takes on the leading citizens of Florence; Machiavelli, who was known in his own time as a playwright and not a political philosopher, was even bold enough to put such ridicule in print. The 1504 play Le Maschere is tragically lost, but by surviving accounts it lampooned “under feigned names, many citizens who were still living.”†

While not scribbling pasquinades and getting laid, the Second Secretary had matters of state to attend to. We have met him in these pages, as the Florentine ambassador to the court of Cesare Borgia; Machiavelli could not help but admire the condottiero‘s ruthlessness. Machiavelli also represented Florence in Rome, Spain and France.

Showing an equal aptitude for politics by other means, Machiavelli moved the Florentine military muscle towards a citizen militia, presciently replacing its dependence on mercenaries. In 1509 this force captured Pisa.

But Machiavelli’s excessive regard for this strategic advance married to his excessive affinity for the republic of Piero Soderini undid him in the end. While the First Secretary, Adriani, quietly cultivated contacts of various political persuasions, Machiavelli went all in against the stirring Medicean party. This became a problem when the fortunes of peninsular war drove Florence’s French allies away, leaving the city ripe for recapture by Giuliano de’ Medici, who also happened to be the brother of the pope in waiting.

In 1512, a hastily-assembled city militia of about three or four thousand infantry and 100 men-at-arms met an overwhelming Spanish-Papal-Medicean force at Prato. Scrambling to defend a lost cause, Machiavelli had mustered about a third of the militia and was trying to organize the city’s defenses. Florence’s crushing defeat in this battle and the ensuing civic massacre in Prato (with “countless murders, sacrileges and rapes”) convinced the Florentines to depose Piero Soderini and throw open the gates to Giuliano de’ Medici.

This was the end of Machiavelli the statesman … and, of course, the birth of Machiavelli the philosopher. The ensuing 15 years’ frustrating exile left him no other outlet for his political passions save his pen; needless to say, works like The Prince and Discourses on Livy retain exalted seats in the canon down to the present day. (They made little impression on Machiavelli’s contemporaries; Florentines still knew him for the plays he kept writing.)

The cautious primo segretario Adriani, who could better see where the winds were blowing, survived the transition by having the wisdom not to align himself with the losing party. Whatever the verdict of posterity, the 1510s were Adriani’s time to bask in the center of events while Machiavelli did his work of ages in obscurity.

But what cinched Machiavelli’s unhappy permanent banishment from Florentine politics — notwithstanding unctuous expedients like dedicating The Prince to the Medici ruler — were the events culminating in two February 23, 1513 beheadings.

Machiavelli had been dismissed in November 1512. Four months later, a nascent (or wildly exaggerated) anti-Medici conspiracy led by a republican named Pietro Boscoli came to light. Its chief, and paltry, evidence was little more than a written list of around 20 fellow-travelers, upon which appeared the name of Niccolo Machiavelli. It’s more than likely that the “treason” comprised merely to the idle chatter of some disaffected republicans, but after a generation in exile the newly restored Medici dynasty wasn’t taking any chances.

For the onetime Second Secretary, this meant prison and torture by the strappado. Three months on, he was released to his estate with no political succor save the haunts in his head.

But the head he got to keep — and that was better than one could say for Pietro Boscoli.

Boscoli and one Agostino Capponi were beheaded early in the morning of February 23, a bare eight hours after their death sentences were announced. Their last hours were recorded as a Recitazione by a young friend named Luca della Robbia: the tender Passion scene of Boscoli in particular struggling to come to grips with his shockingly sudden fate. The full narrative can be found in translation by Alison Knowles Frazier in The Art of Executing Well: Rituals of Execution in Renaissance Italy. We excerpt a little taste below:

At about 8 o’clock, having had his supper, Boscoli was brought with his legs in irons to the chapel where … he was told that he had to die …

Pietro Paolo cried out “Oh Pietro Paolo, oh poor Pietro Paolo! What has become of you!”

Then I, moved by the greatest compassion, seeing my beloved friend in such great distress, went first to him as lovingly as I could, with a gesture full of mercy, and greeted him like this: “God save you, dearest friend. ‘Do not fear those who kill the body, for they cannot kill the soul.’“

Poor Pietro Paolo struggles on here for 15-odd pages in evident anguish, veering between practical considerations of the family he is leaving behind and whom to rustle up as his last-minute confessor, and his uncertain spiritual readiness for death (he was particularly upset at being told of his fate after dinner, for “I am too loaded down with food, and I have eaten salty things, so that I don’t feel able to join my spirit to God”). Della Robbia stays with him the whole time; in the latter’s introduction, he says he “noted diligently all his words, both questions and replies, and kept them in my memory … that such a great and well-formed example of strength and spiritedness would not be lost” and recorded them faithfully later on.

By the end, Boscoli has reconciled his mind to the scaffold.

He is escorted down the stairs from the chapel of the Bargello to its interior courtyard where

leaving the first step, he encountered the Confraternity’s‡ crucifix.

“What am I to do?” [Boscoli] said.

“This is your captain, who comes to arm you,” the friar responded. “Greet him, honor him, ask him to make you strong.”

Then he said, “Greetings, Lord Jesus. I adore you, hanging on the cross. Make me, I beg you, like to your Passion. True Lord, I ask you for peace.”

And thus, going down the second step, he kept commending himself, saying, “‘Into your hands, Lord, I commend my spirit. You redeemed me, Lord, God of truth.’” When he was on the little platform of the stair, he said, “Is it enough, a good preparation towards God? For I feel some battle. Recall to me those three things.”

Then I, who was behind him, said, “Well you know that it is enough. Say to him, Fra Cipriano, that verse by David, ‘Your ear heard the preparation of their heart, Lord.’”

“Okay, yes,” the friar replied, “Your ear heard the preparations …,” and told him once again the three things.§

And he answered, and said, “‘Let your ear hear the preparation of my heart, Lord Jesus.'”

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Then the executioner, because he wanted to put a kerchief over his eyes, asked his forgiveness and offered to pray to God for him.

“Go ahead and do your duty,” Pietro Paolo said. “And when you have put me at the block, leave me like that for a bit and then finish me off, and that you pray God for me, I accept.”

The reason why he asked for a little time at the block, was that he had all night long always desired a great joining with God and he didn’t feel that he had achieved it as he desired, so that he hoped in that last moment to make a great effort and so to offer himself wholly to God …

And placing himself down, and the executioner, giving him the shortest time, cleanly removed his head, which, so cut, continued to move its mouth for a time.

Agostino Capponi, whom della Robbia has seen only glancingly over his long narrative, follows Boscoli. Although Capponi required two blows of the executioner’s blade, he perhaps went into the hereafter with a soul better at peace — for he “retained on his face a certain wry expression, perhaps not distant from true sincerity.”

* Summary of Machiavelli’s career based on William Landon’s Politics, Patriotism and Language: Niccolò Machiavelli’s «Secular Patria» and the Creation of an Italian National Identity.

** Machiavelli’s clerk Agostino Vespucci — a cousin of the explorer Amerigo Vespucci for whom the American continents were named — made the headlines recently when discovery of a scribble he left in the margin of a 16th century text established the identity of the long-mysterious first lady of Renaissance art, Mona Lisa: she was Lisa del Giocondo, the wife of a Florentine cloth merchant.

† Landon says the primo segretario Adriani encouraged Machiavelli to publish this play, even though Adriani himself is one of its targets — in Landon’s view, because Adriani was playing a long game for power, and revenge: quietly encouraging Machiavelli’s excesses while positioning himself politically to profit from his consequent fall.

‡ The Confraternity of the Blacks: a lay brotherhood associated with Florence’s [former] Chiesa di Santa Maria Vergine della Croce al Tempio, tasked with the spiritual assistance of prisoners condemned to death.

§ Shortly before proceeding to execution, Boscoli steeled himself for the ordeal by resolving that “In this journey I have to have three things. I have to believe the faith. I have to have firm hope that God will pardon me. And the third is that I have to suffer this death for love of Christ and not for others.”

On this day..

• Feast Day of St. Polycarp of Smyrna
• 1719: Lt. Edward Bird, ungentlemanly
• 2000: Ahmad Ismail Uthman Saleh and Ahmad Ibrahim al-Sayyid al-Naggar, renditioned
• 1807: John Holloway and Owen Haggerty, sworn away
• 1554: Henry Grey, Duke of Suffolk
• 1828: Antoine Berthet, Stendhal inspiration
• 1939: Alexander Kosarev, Spartak Moscow patron
• 1906: Johann Otto Hoch, bluebeard
• 1629: John Dean, boy arsonist
• 1942: Boris Vilde, linguist
• 1885: Not John "Babbacombe" Lee, the man they could not hang
• 1838: Andrea Rondola but not Peppino