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Niccolò Machiavelli. His name is synonymous with cunning and clever schemes, the ultimate ruthless strategist.

But how clever was he? Image
One summer day, Machiavelli visited the famous mercenary captain Giovanni delle Bande Nere at his camp. Giovanni invited the writer to drill his company in the maneuver’s described in his book “The Art of War”.

Machiavelli enthusiastically took up the offer. Image
It was a disaster. Machiavelli got the troops completely turned about and couldn’t restore order.

Giovanni let the Florentine flounder for hours in the sweltering heat before stepping in and setting things straight. There was a lesson in this… Image
Machiavelli had bragged that the experienced commander was so successful because he had learned the lessons from Machiavelli’s own book.

Giovanni considered his own hard-won experience somewhat more valuable, and wanted to prove it. Image
This possibly scurrilous anecdote illustrates a common view of Machiavelli by his contemporaries, that he was a theorizer more than a competent man of action.

Nothing else in Machiavelli’s career seems to disprove that.
In 1494, the Florentines expelled the Medici, fed up with their avarice and cruelty. They established a republic, and Machiavelli found employment as a secretary in the chancery—his classical education had brought him to the center of politics. Image
Machiavelli quickly rose to prominence and was sent on important diplomatic missions to other Italian and European states. During this time he also continued his reading of the Classics and promoted an ideal of republican virtue inspired by Rome.
Eventually he was put in charge of Florence’s militia. Disgusted by the depredations of the condottieri who had made fortunes of Italy’s incessant wars, and fired by his own republican idealism, Machiavelli organized a new force built around citizen-soldiers.
But he was not terribly successful. During the siege of Pisa, he tried to use a scheme dreamed up by Leonardo da Vinci to divert the Arno, the city’s only source of water, and force the Pisans to capitulate.

It was a complete failure. Image
Machiavelli proved not to be a good manager of men. The channels were dug too shallow, and eventually the Pisans sallied out and destroyed the undefended weirs diverting the water.

He seemed to prefer clever schemes to hard-nosed tactics.
Ultimately, it was mercantile Florence’s gold that conquered Pisa. It allowed Machiavelli to bribe neighboring cities not to intervene and to keep the militia in the field long enough to starve Pisa out. Image
But eventually, the militia had to fight professional soldiers. In 1512, during the War of the League of Cambrai, Spanish troops intent on restoring the Medici besieged the Florentine city of Prato, guarded by the militia.
Image
The militia was hopelessly overmatched and the Spanish brutally sacked the city, prompting the horrified Florentines to hurriedly open their own gates. The Medici were back in power.
Soon after their restoration, Machiavelli was implicated in a plot against them. He was questioned, tortured, and ultimately exiled to the Tuscan countryside.

Although his life there sounds idyllic, Machiavelli desperately missed being in the thick of things. Image
It was there that Machiavelli wrote “The Prince”. It is commonly believed that he wrote it to get back in the Medici’s good graces, perhaps in the hope of being hired to a government position. Image
But if a good prince is advised to maintain a hypocritical moral façade, the last thing he would do is hire someone who says as much outright. Especially rulers such as the Medici, who had so recently been driven out of Florence for their extravagance and venality. Image
They were still not secure on their throne and had enemies everywhere—why would they possibly reward Machiavelli for pointing out their underhanded maneuvers? Writing “The Prince” was the very worst thing he could do if he wanted his job back.
This is why many people in the 18th century just assumed "The Prince" was satire—they though he was calling the Medici on their game. What else to make of a book so patently absurd?
But poor Niccolò had had a rough few years. He saw his beloved republic fall, lost his job, was tortured, and exiled from his native city. His only comfort was reading the ancient authors, which he did religiously every evening. In the preface to “The Prince” he wrote:
“When evening has come, I return to my house and go into my study. At the door I take off my clothes of the day, covered with mud and mire, and I put on my regal and courtly garments. Decently reclothed, I enter the ancient courts of ancient men…”
“There I am not ashamed to ask them the reason for their actions; they in their humanity reply to me. For the space of four hours I feel no boredom, I forget every pain, I do not fear poverty, death does not frighten me. I deliver myself entirely to them.”
Perhaps this was the real reason he wrote “The Prince”, to console himself for a life full of sorrows, disappointments, and failures.

If he heard that his name would one day be synonymous with cutthroat realpolitik, he might laugh.
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