[A conversation that might have happened if Machiavelli had channeled Donald Trump.]

“You can discover what your enemy fears most by observing the means he uses to frighten you.” --Eric Hoffer

Many of us have heard—if not used at least once—the word Machiavellian as it applies to the extremity of power. Over time the adjective evolved into cunning, duplicitous and unscrupulous. Who started this semantic roll? Why, the eponymous man himself, of course: Niccolo Machiavelli, whose drive for power had impressed many people and frightened many others.

I am the archangel, Michael. My heavenly function is to rid the earth of fear. Accordingly, I wanted to meet Machiavelli to hear his side of the story and, perhaps, to understand how he had generated fear. Maybe he had something to teach me as well in light of the contrast between his militarism and my pacifism. After all, newly chosen, he was to be commander in chief of the Florence militia.

He was also the person many considered an autocrat who’d pitched his share of kindling onto the flames of misogyny. Accordingly, he suffered a secret that—as I had discovered—revealed a surprising vulnerability to women as well. It was not quite the picture of him we all had imagined, nor was it the image he had wished to project. (More on this revelation later.) I met Machiavelli for the first time one late afternoon in 1512. An impressive figure clothed in the orange and gold robes of a Florentine official, he stood at his open doorway. Within the room, oil lamps hung from the ceiling. Stabbing at me through swirls of smoky light was a long nose wedged between two azure eyes whose gaze traveled upward from the rubies on my fingers, to the fur collar of my jerkin, to my russet wig. Then, with the impact of a flash-flood, our eyes met. In his I saw an instinctive intelligence whose pragmatism sparked boldness and daring.

In preparation for this encounter, I had taken the form of a human being whose persona, both in speech and appearance, was common during Machiavelli’s day. I introduced myself as Jacopo Berengario da Carpi, a publisher who lived near the Palazzo Vecchio. Holding his gaze, I announced, “Niccolò di Bernardo dei Machiavelli, as a publisher who has read your latest manuscripts, The Prince and The Art of War, I am impressed. I fear, however, that your success as a leader will be limited—unless you soften your position on authoritarianism.”

He looked surprised. “Soften…? In reading The Prince, did you not understand the means by which to achieve power as well as the means by which to keep it?” His finger waggled at me. “The danger of power and softness commingling is that each will dilute the other.”
I assured him that although I did read The Prince, I found its author—Machiavelli himself—to come off as a braggart. I added with a wink, “Even as a narcissist.”
His brow jumped. “Do you wish me, a new leader, to play down my exceptionalism? Would you wish me as well to shrink the distinctiveness of Italy itself? Who but me knows best how to water my own garden?” He poked me in the chest and declared,

“When a leader blooms, so do his people.”

“But you say that the people of Florence are in danger.”

“Indeed they are. Florentians have lost not only their pride as a city state, but are in danger of losing their lives as well. I can resurrect that pride by smashing our enemies and by giving fair warning to those who take advantage of us. First I would start with the Spaniards.”

I stood facing him in the open doorway. “You seem very confident about your ability to save Florence.”

“Why do you look so shocked? My military theory far surpasses the knowledge evinced by those generals who cannot comprehend the true evil of our enemy.” Playing in the street behind me, youngsters whooped. “Allow me to state a truism,” Machiavelli said. “Most officials cannot govern themselves. And if one cannot govern oneself, one can govern no other.” With a raised finger, he pointed out, “I am now the military leader of approximately 12,000 Florentine troops. My only goal is to make Florence safe again.”
“Not all Florentians believe in your type of rule, however.”

He shrugged. “Those who reject my brand of leadership are tender souls. They squirm in the presence of power—even though the execution of that power can save their lives and the lives of their loved ones.” He smiled. “Is it not suicidal to meet a charging dragon with the swat of a feather?”

“See? It is this kind of language that unsettles people. Dragons? Suicide? You’re playing upon people’s fears.”

“Really? Should they not fear those who wish to destroy them? Should we believe that the heart of our enemy is kind and redeemable?”

“Is this how you view Spaniards? Perhaps even the French? As dragons?”

“Not all. Only those who threaten the health of Florence—whether that health is economic or physical. I assure you: such threat, under my leadership, will be squashed immediately.” He squinted. “Meek people, of course, will shudder at these words, which I know they view as combative.”

“You seem to have an aversion to softness, Machiavelli. Those possessing this trait you call tender souls.” When I reminded him of Jesus’s vision of the meek inheriting the earth, he wagged his finger. “The meek will inherit only suppression, for they know only obedience.” Then, the slight pressure of his palm against my chest—which just hours ago was vaporous—indicated the termination of our meeting.

Standing in the doorway, however, I didn’t budge. “Do you consider women foremost among the meek?”

His palm easing off my chest, he thought about the question. “Women have done nothing to make the city states stronger, have they?”

I didn’t reply.

“Do you believe that in the name of gender equality,” he continued, “I should hamstring the muscle of might just to accommodate the delicacy of women? That perhaps I should rip them away from the nursery and place them instead on the battlefield where they suffer the wail of the dying instead of that of their babies?”

“You think that all women belong in the nursery?”

“Well, certainly men do not.”

For the next few minutes I cautioned him against souring the milk of human kindness, which, I noted, tasted sweetest in the maternal breast.

He laughed. “Then ask infants, not leaders, to suck at the teats. Despite what fragile people want to hear or wish for, today’s Italy is not a tranquil lake over which angels flutter. Rather, it is an ocean, often stormy.” He began to pace, his right hand gesticulating, the fist of his left hand locked to his hip. “Lurking deep in that ocean are monsters—foreign powers wishing to control us, perhaps even enemies within who hate Italy. Those enemies can locomote to the surface of that ocean with surprising and fiendish swiftness, their teeth chomping.” With a twinkle, he added, “And it is always the tender among us who are the first to be gobbled up.”

Allowing me to inch into clouds of oil hovering just below the ceiling in his room, he skimmed over to an oaken table from which he poured ale into two tankards, one of which he handed me. “In such a hazardous life,” he pointed out, “there must be leaders fearless and fierce. All other people, naturally, will be wise to follow.”

“And you see yourself as a leader—the very man who can keep Florence safe?”

He smiled. “I can traverse political and military terrains previous leaders had avoided. I know how to protect. I also know how to negotiate. I am a persuader. But understand this: If negotiation fails, conflict occurs, which may very well lead to war.”

There was a brief silence, except for the children shouting and a dog yipping somewhere behind me in the street. “Given all that you have just told me, are you actually prepared to shed the blood of Florence if it came to that?”

Eyebrows raised, he stared at me. “What a weepy question, which only exposes your naivete.” He sighed. “It is the flow of blood, not the gushing of tears, that brings peace. Do you not know that?”

Without sipping the brew, I raised the tankard to him. “To peace, then! And to you, Machiavelli. The new leader of Florence. The warrior!”

Chuckling, he shook his head and flicked soot off the orange cuff of his sleeve. “Well, Sir, I am actually a theoretician. I have never fought in battle.”

“What? Never?”

His shrug was less apologetic than defiant.

“Now that is amazing,” I said, “considering the knowledge you tout in The Art of War. Good Lord! You have written seven separate manuscripts on how to succeed in battle, yet you have had no military experience?”

His lips pursed. “None whatsoever. Just look upon me as a juggernaut stomping on the norm. I want to upend the old ways of doing business, the old ways of fighting wars. The old ways of governing. By not making Florence strong enough, the status quo, instead, has made her vulnerable.”

I pointed out that Sun Tzu was a general in the 6th century BC who wrote a book also entitled The Art of War. “But unlike you,” I made clear, “he actually did taste blood. How can you lead the Italian states in battle if you have earned your fame solely with the quill and your financial advice to princes?” I paused. “Can you admit that Sun Tzu’s experience as a warrior makes your military observations—armchair ones at best—less persuasive?”

“Experience can be overrated,” he shouted, striding to a bowl of water on the table. After splashing his face, he apprized me that one need not die in order to understand death. “Certain insights,” he said, “reside in the treasury of our imagination, in the archives of wisdom—rather than in experience.”

He patted his face with a towel. “I know how to disregard fruitless policies that bring to the enemy’s table honey cakes instead of an iron fist. As long as Florence embraces the niceties of politics and the politics of niceties, it will always succumb to the ferocity of its foe.” He added, “We have many foes. Believe me.”

I suggested that as the new leader so eager to disregard custom, he seemed to care little about which sacred cows he kicked. He looked hard at me. “If we continue to give grazing rights to the old ways, we will be destroyed not only by Spain but by France as well.”

He stared at me.

“What…?”

“You asked me about God before,” he said. “Although I prefer the Old Testament to the New, allow me to note something from the latter.” He smiled. “Not that I am a reader of the bible, but this piece stayed with me.”

He continued staring at me.

I nodded. “Go on.”

“There’s a time to heal and a time to kill. Is this not true?”

I found myself half shrugging and half nodding and, frankly, a bit unsettled because I could not deny the soundness of the question. I must have made a face because he cocked his head and asked whether I believed in survival. I told him I did, then noted, “But I also believe in love. Without love mankind cannot survive. And as somebody so enamored of power as you are, you need to show your heart, not only your fist. The more we love, the less we fear.”

He paced a tight circle around me as if I were a ribboned package of suspicious content. “What an extraordinary statement. Drenched totally in sentimentality.” Continuing to circle me, he suggested that people who love most, because of their reluctance or inability to fight, are the first to capitulate to the enemy.

“Survival demands ruthlessness,” he explained, “and ruthlessness grows from power.” He sipped more ale. “You talk of love? The only love informing military decisions is love of country. I love Italy. I love Florence. And I shall make them safe again.” He added, “Believe me.”

The children and the dog had left. The street outside now was quiet except for the muted chatter of occasional passersby.

“But suppose,” I said, “you had not been chosen to be Commander in Chief? What do you think would have happened to Florence?”

He turned away in thought, then faced me and replied with disarming surety. “Florence would find herself swirling in the rapids as she surges toward the waterfall. The weak—those who cannot or will not fight—will be incapable of grabbing onto the jutting branch, the one thing that can save them.”

Turning up one of the oil lamps, which spread an amber shadow along the wall behind him, he said, “But know this: not all among the governed are meek. Many only pretend to be. They are rivals who feel caged because they are not in charge. Enter that cage as a leader and, like wild animals, they will tear you apart…unless you enter with a savagery greater than theirs.”

Flapping the cloth at the smoke filling the room, Machiavelli added, “I know that as an advocate of civility, you prefer the smile to the snarl.” He patted my back. “But remember this: Regardless of its civility or its genial face, the lamb will always be eaten by the lion.”
Wooden wheels of a cart clacked over cobblestones a few feet from his open doorway.
“I know that you identify with the lion, Machiavelli. So, tell me please: Is there nobody who rules you? Not even God?”

Nostrils flaring, he grinned. “With his army of angels to battle evil, God knows all about power.”

“Does he reign over you?”

Machiavelli smiled but did not answer.

“Who, then? Satan…?”

His forehead wrinkled. “Satan is a fallen angel.” His index finger, now hooked like the beak of a rooster, pecked at me. “And no angel, fallen or not, can ever rule Niccolo Machiavelli.” Smirking, he raised his tankard. “Cin cin!”

***

After coughing from the smoke, he suggested we continue our conversation outside. Beneath a sun still strong at four in the afternoon, the gold and orange threads embroidering his garment glinted as his legs maintained a swift pace along the cobblestones.

It had become clear to me that Machiavelli was uncomfortable discussing love. So, granting that the lion will always devour the lamb, I asked him to name an alternative to love. His answer: Fear. He assured me that the sensible lamb will always—and should always—fear the lion and make sure to avoid his company.

We discussed the difference between governing with love and governing with fear. He told me that love is susceptible to unconditionality. Unconditionality, he warned, invites abuse. He said that followers perceive a leader’s love as a gift in perpetuity. “They mutter, I can betray my king because he loves me. Therefore, he will forgive me.”
Keeping up the brisk pace, he glanced at me. “See the trap? By contrast, fear does not accommodate forgiveness. Fear brings darkness and followers follow best in the absence of light.”

“Yet too often fear makes us do bad things.”

He chuckled. “Sometimes, if you wish to live, doing bad is good.”

“But in a different light, it is also bad to believe you can do no wrong. You seem to consider any criticism of you a betrayal.”

He glanced at me, then looked straight ahead, his expression solemn. “Allowing even the slightest criticism to go unchallenged cracks the door enough for the enemy to shove his foot in. If enough fortifications in the king’s castle are breached, he will be vanquished.”
We entered the Piazza della Signoria, where street musicians played their banjos and lutes. Sparrows frolicked on the heads of marble statues standing equidistant from one another. Machiavelli grazed a thumb along a portion of marble of every figure we passed, as if he needed to daub his mark for posterity, as if to say—See? Machiavelli was here. “If he wants to survive,” he informed me, “a true leader facing the enemy must be as merciless as the owl snatching up the rodent. Victory is what matters—not love or the frippery of moral intent.”

“If you care so little about morality, as a leader would you tell lies to maintain your governance? Would you lie to advance your agenda…?”

He snickered. “Do you not possess a single pragmatic bone in your body?” Taking my elbow to hurry me along, he said, “A ruler who deceives well will find followers well willing to be deceived.” Deception, he emphasized, if it is to be used at all, must serve achievement. “My goal is to ensure that the people of Florence live in safety. Who in command of his faculties can fault this objective? Those who do are not friends of Florence.”

He stopped walking, faced me and grabbed my shoulders. “Accomplish your goal, Jacopo, but do it without over-thinking, regret or apology.”

“Look, there are all kinds of goals that—”

“The goal of approaching a woman, for instance.”

“What?”

We resumed our stroll.

“Suppose you see a beautiful woman yet you hesitate to step toward her for fear of rejection. Is it not better to approach her and risk reproach than not to approach her and suffer self-reproach?” The king’s crown, he maintained, is itself an aphrodisiac regardless of who wears it. He said further, “Given my status—my very authority—indeed I can enter the orchard of any beautiful woman and eat of her fruits if I so wish.”
This kind of talk made me uncomfortable, and I felt a flutter within my arms, which, only hours ago, had been wings.

Then he cautioned me: “Only powerful men know how to use their potency wisely. Weak people may want power but they cannot wield it because of its weight, which eventually crushes them.”

“Yes but think about those you call your enemies, like the rulers of Spain and France. They have power too, which, I assume, threatens yours.”

“That is why my grip upon the reins of sovereignty must be as unyielding as the root of a tree clutching the earth.” He stopped walking, faced me and again clapped both palms onto my shoulders. “As a leader you must never apologize for or loosen the tightness of that grip, and never express remorse for the extremity of any decision you make—even the unorthodox ones—to keep your people safe.”

“Are you telling me that you have never regretted any of your decisions?”

In thought, with two fingers he pinched his lips together. “Perhaps once. With a woman. But it is best to preserve this subject for a later discussion.”

When we reached the center of the Piazza, something gnawed at me. Maybe it was Machiavelli’s amoral absolutism or his antipathy to empathy. Surely, I thought, in the exercise of power in his world there must be even at its fuzziest some semblance of ethical gray. Did he believe that the end justifies the means regardless of the situation?
With this question in mind, I posed the following situation: I was a king whose only objective at the end of my long journey was to reach my kingdom. Spurred on by my haste, however, the horses knocked over an innocent servant, who died. Should I not express remorse and censure myself for what I had done? If for no other reason than to obey the calls of conscience?

He stopped walking, the gold and orange of his robe now dim in the fading sun, and scolded me on my “abandonment of the primitive.” Having acknowledged the tragedy of the servant’s death, he posed this question: “Do you not know, however, that mankind stupidly has grafted the twinge of conscience onto the face of necessity?”

When I didn’t reply, he clasped my arm and joggled it. “Dear Jacopo. Many times conscience gives your enemy life today so that he may kill you tomorrow.”
I shrugged free of his hold, which was quite firm. “Your tone is very cynical.”
“My tone?” He barked out a laugh. “Look at the first Italian war against King Charles the Eighth. Since then Italy has faced enemies who have crushed our skulls with war hammers, slit our throats with daggers and impaled our eyes with the crossbow—-and you are concerned about insulting them with tone?”

Upon continuing our walk, he said in a more subdued voice, “Would you not flog or brand with hot irons an enemy soldier for the purpose of extracting information if such information can save the life of even one Florentian?”

When I didn’t respond, he put his hands on his hips and glared at me. “You cannot answer this simple question? Are you altogether mindless?” He paused. “I know what you are thinking. Cruelty for any reason is wrong. You prefer politesse to survival, do you not?”

“I believe we must never cross a certain line.”

“Indeed?” He laughed. “Back to your little story and the guilt you carry for having killed your servant. You are the king. What if, by swerving to avoid that servant, you toppled out of the carriage and were killed yourself, thus unable to reach your kingdom—which, in your absence, would fall apart?” As he regarded me, he held out his arms solicitously. “Is the life of one servant more important than yours? Or that of your kingdom?”
I pondered his question longer than I had expected to. “Sure—if I were that servant.”
He threw his head back, laughed and pounded my back. “I like you, Jacopo.” He pointed out, “People think me callous and aggressive. But the words I speak have heretofore been avoided by those who shrink from confrontation…by those who too often display a vision that, in its sugared glaze, blurs the sharp edges of reality and leads us into a fiction that spells our doom.”

He added, “Those who consider me incapable of governing are terrified of change and of whatever tentacles of power grow from it. To them, who are my vilifiers, I say this: We must choose excellence over mediocrity, aggressiveness over cordiality and the welfare of Italy over that of all other countries.” In contemplation he whisked at his chin, then shook his head. “Those who think otherwise are imbeciles.”

***

Over the years, I kept thinking of the one subject Machiavelli put off for a “later discussion”: women, love and regret. So one early evening years later in June, I reappeared at his doorstep. A fresh web of wrinkles worried the corners of his mouth and eyes. To me, however, he said, “Jacopo! You have not changed a scintilla!” We revisited the Piazza della Signoria, where he told me about his ten-year affair with a woman he called La Riccia.

“Why did it end?” I asked.

“She chose power over passion.”

“I don’t understand.”

Noting his sudden pallor, I led him to a bench beneath a willow tree. No longer a Florentine official, Machiavelli wore a linen shirt, doublet and long hose. He leaned forward, elbows on knees, chin in his cupped palms.

“Over the course of my life, I have had several affairs.”

I said nothing.

He nodded. “But La Riccia was the most egregious among those women who gravitate to men of wealth and power.” Sparrows burst off the helmet of one of the marble statues in front of us. “Unfortunately for me, the Medici, having returned to rule, incarcerated me, then banished me from Florence.” He mopped his sweaty forehead with a cloth. “Nearly indigent, I lived on a small estate my family owned at San Casciano.”

“You? Indigent?”

He nodded. “My position in life had dissolved like the afterglow of sunset. Imagine! I, who among all men know best the art of finance and commerce, was no longer the one advising princes. No longer the vigorous defender of Florence. No longer the man in charge.” He patted his cheeks with the cloth. “Accordingly, with my status limping, I had visited La Riccia in Florence so often, in fact, that she referred to me as…” He stopped, sucked in a ragged breath and snorted. “…as a house pest.”

He looked away.

“As a…house guest?” I said.

“House pest!” he shouted. “Pest!” He leaped up from the bench and glared down at me. The edge of one hand chopped into the palm of the other. “Would such a courtesan ever have said that to me had I been restored to power?”

“Yet you stayed with her.”

He shrugged as we started back. “A hungry man must keep food in the nearest pantry.” He glanced at me. “At our last meeting so many years ago, you said that love is the glue that binds. For La Riccia and me it was true at the beginning. That love loosened, however, simply because it was not bonded to fear.” He turned away, then looked at me. “Do you not see? Because my power was gone, she no longer feared me.” He added, “Fear, you see, lives longer than love.”

The air held the shimmer of a balmy dusk. After glancing up at scarlet plumes shredding in the sky, we moved along silently. Machiavelli said, “Roads that once sparkled in their welcome of me are now dull.” He wagged a finger. “Remember this, Jacopo: women want leaders, not followers.”

“But what about women who themselves are leaders?”

“If they exist, then to keep the peace, they would do well choosing men who follow, for two leaders sailing the same marital ship will always battle for supremacy.”

“Perhaps it is best, at this point in our life, to remove love from any discussion of politics, Niccolo. Do you agree?”

He sniggered. “Winning is winning. Is not romantic love, like so many other jousts, played out on the chessboard of politics? But I have learned this: The brave suitor sensing his loss is distinguished by his willingness to cede the game rather than continue ignominiously toward checkmate.”

We turned a corner and paced down a path now dim in the enclosing darkness. I waited a few beats, then told him I knew he was married.

“Yes,” he replied. “To Marietta.” He paused. “The milk of human kindness you had once spoken about? Its sweetness and bounty?” He sighed. “It does run through my wife’s breasts.”

“And La Riccia?”

He turned to me, his eyes rueful. “What runs through her breasts is ice water.”
“Wouldn’t that make her a good leader? One far removed from the nursery?”
We stared at each other, neither speaking. Within seconds, however, his lips curled into a smile. Then a deep guffaw clambered up his belly. He smacked my shoulder and we both laughed.

“I have met my match, Jacopo.” He waited a beat. “Are you hungry for supper?”
We left the Piazza and stopped at a butcher shop. Behind the window skinned carcasses of wild pigs hung from pegs. After contemplating a porcine repast, he chose, instead, a supper of lamb in a nearby café. We finished off the evening back at the Piazza, where the perfume of roses scented the evening.

We selected a bench next to the statue of Alberico da Barbiano, a teacher of military science. Puffing on his cigar, Machiavelli stared at him wistfully and grinned. “He reminds me of myself when I led the Florentine troops against the Spaniards eight years ago.”

“I remember. And I acknowledge that power, certainly for you, had its rewards.” I cleared my throat. “But you did lose the battle, did you not?”

He stared at me. “Only because, out of loyalty, I had not fired two of my generals, who deserved firing.” He turned to the statue of Barbiano, whose face angled up at the moon, which, tonight in its orange hue, gazed down at us with the righteous grin of a blameless warrior.