But if Machiavelli had little of substance to offer the Duke, he was encouraged by Valentino’s less belligerent tone. Gone were the tirades he had indulged in during their prior meetings. His Excellency, Machiavelli relayed, “declared that he had always desired the friendship of Your Lordships, and if in this he had failed it was not through his own fault but because of the malice of others.” It was a laughable assertion, and Machiavelli knew it. Valentino’s sudden amiableness was nothing more than a reflection of his weakened position, but Machiavelli urged his bosses to take advantage of the Duke’s vulnerability by striking a deal on favorable terms. He held to this course even after hearing news, coming a week after his arrival, of the battle of Fossombrone, where Valentino’s forces were routed by the rebels. Nothing, it seemed, could shake Machiavelli’s confidence in Valentino’s star. In his report to the Ten he concluded “his enemies can no longer do much harm to His Lordship.” The source of Machiavelli’s confidence was largely Valentino himself, whose almost superhuman belief in his own powers rubbed off on the Second Chancellor. Greeting the Florentine emissary with his usual bluster, Valentino laughed off recent reversals, claiming that “with the king of France in Italy and the Pope, our Lord, still living, these two would light such a fire beneath [the rebels] that they would need more water than they possessed to put it out.”
The reports Machiavelli sent back to the Ten on an almost daily basis demonstrate his deepening understanding of power politics. Barred from conducting substantive negotiations, he had to content himself with offering his analysis of the increasingly tense situation. His friend Buonaccorsi worried that on occasion his advice was “too forceful,” that he should instead stick to a dry narration of the facts, but Machiavelli’s bosses found his insights invaluable as they attempted to craft a policy that would provoke neither the dangerous and unpredictable Duke nor his equally formidable rivals.
Steering a middle course between two uncomfortable alternatives remained the government’s preferred tack, but the reluctance to follow a bold course was reinforced in this case by the chaos reigning in the halls of the Palazzo della Signoria, great even by the lax standards of the Florentine Republic. Ironically, the current confusion was actually a sign of progress. It resulted from a decision, taken shortly before Machiavelli’s departure, to reform a government that all acknowledged was structurally flawed. With the top officials—including the Signoria, the eight priors, and the Gonfaloniere di Giustizia, who made up the chief executive—rotating in and out of office every couple of months, the government consisted of amateurs with little expertise and less courage. Foreign governments complained that decisions arrived at one day were reversed the next, or, more often, were never made at all since the safest course was to avoid taking a difficult stand and to pass the resulting mess along to one’s successors. Florentine prestige plummeted as the hapless republic lurched this way and that. Machiavelli later derived a general principle from his unhappy experience in Cesare Borgia’s court. “I think taking a stand between two belligerents is nothing short of asking to be hated and despised,” he wrote to his friend Francesco Vettori, explaining that both sides would come to regard you as weak and treacherous. It was this policy—or deliberate lack of one—that caused the government of Florence to be looked on, as he so memorably put it, as Sir Nihil.
The only remedy for this fatal lack of direction was to strengthen the chief executive. In September, in a radical departure from past practice, the Great Council voted to make the office of Gonfaloniere di Giustizia a lifetime position. The new Gonfaloniere would be much like the Venetian Doge, an embodiment of the majesty of the state who, through his lifetime tenure and elevation above the daily strife, would provide firm direction to a government deranged by frequent and chaotic elections. After an initial roster of 236 possible candidates was submitted, the people’s choice—arrived at on the third ballot—fell to Piero Soderini, brother of the Bishop of Volterra and a man with a long and distinguished career as a diplomat. He owed his election not only to his well-known integrity, but also to the fact that he had spent so much time abroad in service to his country that he had made fewer enemies than most of his peers. In Soderini the Florentine people seemed to have found themselves a wise and scrupulous leader, a man of personal virtue who would put the welfare of the state ahead of family ambition.
Machiavelli welcomed the selection of Soderini. Not only was Machiavelli close to the new Gonfaloniere’s brother—the two having served together on the first mission to Valentino—but Piero himself was well acquainted with the Second Chancellor’s ability. Agostino Vespucci soon confirmed Soderini’s high opinion, passing along the Gonfaloniere’s kind words after hearing one of Machiavelli’s reports: “The writer who wrote this in his own hand has much talent,” Soderini told his colleagues, “is endowed with much judgment, and also no little wisdom.” Another friend, Niccolò Valori, was even more emphatic, declaring “I believe he has become your great friend.” With such a man in charge, Machiavelli could expect his own career to prosper.
Though Soderini had been elected on September 20, more than two weeks before Machiavelli set out, he did not take office until November 1. In the meantime, little could be accomplished. Machiavelli did his best to deflect Valentino, who was pressing Florence to join him. “Your Lordships write to me about temporizing, not committing you,” Machiavelli grumbled, frustrated at being placed in such an awkward position, though he added hopefully that already “the new law [for the Gonfaloniere] has raised the reputation of our city so high that one can scarcely believe it.”
Throughout the remainder of October and into November, Valentino and his foes jockeyed for position, while the Second Chancellor tried to evaluate the strengths and weaknesses of the opposing camps. Machiavelli, who used these junkets as an occasion to indulge himself, mixed business with pleasure, wining and dining with the other envoys. It was often hard to distinguish between legitimate government business and partying, and Machiavelli took full advantage of the ambiguity. Between mouthfuls, the ambassadors traded information like merchants at a bazaar, trafficking in gossip and rumor and passing along the more substantial nuggets to their employers back home. “Because courts always include different kinds of busybodies alert to find out what is going on,” Machiavelli wrote late in life when he was advising a young man who was about to take up his first ambassadorial posting, “you will profit by making all of them your friends, so that from each one you can learn something. The friendship of such men can be gained by pleasing them with banquets and entertainments; I have seen entertainments given in the houses of very serious men, who thus offer such fellows a reason for visiting them, so that they can talk with them, because what one of them doesn’t know another does, and much of the time they all together know everything.” Poverty hampered Machiavelli in this regard, but he readily accepted invitations to sup at the well-spread tables of his better funded colleagues.
What he gleaned from these merry gatherings was that Valentino’s hand was stronger than it appeared. Though the early victories had gone to the rebels, Machiavelli warned the Ten not to underestimate the resourceful Duke. “[W]hoever examines the quality of one side and the other, knows this Lord to be a man of great vitality, fortunate and full of hope, favored by the Pope and by the King . . . . His adversaries are insecure in their states, and while they were afraid of [Valentino] before they betrayed him, now they are even more so, having injured him thus.”
In addition to his audacity and supreme self-confidence, Valentino possessed another quality Machiavelli admired. He was, as he later wrote, “a very skillful dissembler.” It was this talent for deception, more than for military strategy, that began to turn the tide in Valentino’s favor. Despite his early setbacks he had managed to avoid catastrophe on the field of battle, and with each passing day he gained in stature while in the camp of his adversaries doubt and dissension grew. Particularly unnerving for the rebels was the fact that Valentino continued to enjoy the favor of
the French King. He gave tangible evidence of his friendship by placing at Valentino’s disposal an additional five hundred lances. With the power of the French crown and the resources of the Vatican behind him, Valentino still had formidable advantages.
Even as he built up his forces, Valentino was pursuing another tack, making conciliatory gestures, floating the idea of an agreement in which he would retain the title of Prince while real power remained in his rivals’ hands. “[S]weetly this basilisk whistled,” Machiavelli wrote in The First Decennale, while the rebels, “these serpents full of poison began to use their claws and with their talons tear one another.”
The combination of veiled threats and subtle overtures soon bore fruit. Machiavelli was on hand when a mysterious rider arrived at Valentino’s castle in Imola. Though “dressed as a courier,” the horseman’s disguise was soon penetrated. Word spread through the streets that Paolo Orsini, one of the leaders of the rebellion, had come before the Duke “to excuse and justify what had occurred and to know his Lordship’s will and to convey this to the other [rebels].”
To Machiavelli, this was the beginning of the end—a sure sign that Valentino’s foes had lost their nerve. The Venetian ambassador in Rome put it even more starkly, concluding “the Orsini might be very sure that they had now cut their own throats.” Valentino himself was delighted with the turn of events. He summoned Machiavelli to his room to gloat over his latest coup: “[T]hey write me pleasing letters,” the Duke told Machiavelli, “and today Lord Pagolo [Orsini] comes to see me; tomorrow it will be Cardinal [Orsini]. Thus they try to pull the wool over my eyes. I, for my part, will play the game, keep my ears open, and bide my time.” On the first of November, after a series of intense negotiations, the two sides signed a truce, agreeing to set aside their differences and resume their interrupted campaign of conquest as if nothing had happened.
What the rebel captains got out of the arrangement, besides “money, robes, and horses,” is unclear. Such trinkets were surely a small price for Valentino to pay to bring an end to a potentially fatal revolt; even cheaper were the promises of reconciliation he made, which cost him nothing yet purchased the time he needed to plot his next move. Machiavelli regarded those who fell for such transparent deceits with nothing but scorn: “it is impossible to believe that [Valentino] can forgive the offense, or that they will ever free themselves from fear,” he mused. They had violated one of Machiavelli’s core principles. “[I]f one must do harm to another,” he would elaborate in The Prince, drawing a general conclusion from a particular instance, “it must be such that it will not give rise to a vendetta.” Not having the benefit of the Second Chancellor’s as yet unwritten primer, the rebel captains committed the cardinal error of provoking an angry beast without taking the precaution of first pulling his fangs.
In the meantime, Valentino was more than happy to make use of the military skills of his former opponents, persuading the rehabilitated mercenary generals, now pathetically eager to demonstrate their newfound loyalty, to lead an attack on the city of Sinigaglia, an Adriatic seaport next on Valentino’s ever-expanding list of conquests.
While Valentino plotted his revenge, Machiavelli was growing increasingly restless. Fascinated as he was by the political machinations unfolding beneath his eyes, the weeks away from friends and family in Florence were taking a toll. “Mona Marietta sent to me via her brother,” reported Biagio Buonaccorsi, “to ask when you’ll be returning; and she says she doesn’t want to write, and makes a thousand complaints, and is upset because you promised her you would stay eight days and no more.” With a new baby to care for, feeling lonely and neglected, Marietta had gone to live with her sister and brother-in-law, Piero del Nero—hardly the wedded bliss the young couple might have hoped for.
Adding to these cares were continuing worries over money. Even after Niccolò Valori had secured from Machiavelli’s bosses an additional 30 gold ducats he remained short of cash. His junkets always cost him more than he recouped from the parsimonious Signoria; in the vicinity of the court even poor lodgings were exorbitant, as were the robes required to avoid cutting a ridiculous figure. Machiavelli was forced to maintain two separate households on an income barely sufficient to keep one in comfort. As weeks lengthened to months, with no end to the mission in sight, everyone’s temper began to fray. Biagio berated Machiavelli for shirking his duties and saddling him with the unpleasant chore of trying to mollify his irate wife. “Stick it up your ass,” he began one letter: “Marietta is desperate, and I have spent 44 soldi in silver from your indemnity.”
Some of Machiavelli’s financial difficulties were his own fault, as Biagio Buonaccorsi suggested. “I wouldn’t be at all surprised,” he reported, “if your raise is going down the tubes, because here the cry among these chancellors is that you’re a cold fish and that you’ve never shown them any kindness.” It is a common refrain throughout Machiavelli’s career. With his sharp tongue and prickly personality, he was often his own worst enemy.
He would have soldiered on with more enthusiasm had he been granted any real authority. More than once the Duke called him in only to scold him for his government’s fecklessness. Machiavelli returned from these harangues exhausted and discouraged. He begged his employers to replace him with an ambassador granted full power to negotiate a condotta. On December 6 he again asked “to relieve the government of this expense, and me of this inconvenience, since for the last twelve days I have been feeling very ill, and if I go on like this, I fear I may have to come back in a basket.” Piero Soderini offered his sympathies, but told him he remained indispensable.
To fight off boredom and depression Machiavelli asked Biagio to send him a copy of Plutarch’s Lives, that ancient compendium of biographies that inspired many a petty tyrant of the Renaissance to imagine himself another Caesar or Alexander. His choice of reading material was likely inspired, at least in part, by his daily sparring matches with the preeminent military figure of the moment, one who might stand comparison with the subjects of Plutarch’s biographies. Machiavelli’s political philosophy was rooted in comparative biography of the kind at which Plutarch excelled. Rather than treating history as the unfolding of impersonal forces, an approach stressed by political thinkers like Hegel and Marx, Machiavelli grounded his science in the psychology of men, their ambitions, appetites, and animal instincts. His advice to a young diplomat was to focus on the character of the ruler: “I say that you are to observe the nature of the man; whether he is stingy or liberal; whether he loves war or peace; whether fame or any other passion influences him; whether the people love him.” Politics as a clash of personalities was an approach that came naturally to someone raised in a city where everyone knew everyone else and where one’s political views were shaped by patronage and family rivalries. Summoned almost daily to appear before the charismatic and ruthless Cesare Borgia, curled up at night with a volume of his beloved Plutarch, history appeared to Machiavelli to be molded by outsized figures who towered like giants above a landscape inhabited by pygmies.
Soon Machiavelli would have fascinating new material to add to the portrait of the tyrant he was already sketching in his mind. In mid-December, Valentino began a tour of his conquered territories. From Imola, the Duke and his army, with the Florentine Second Chancellor in tow, set out for Forli through knee-deep snow, and then south to Cesena. Writing more than a decade later in The Prince, Machiavelli recalled his impressions of the states now under the control of the Borgia Duke. He noted that before his conquest the Romagna “was ruled by impotent lords who would sooner exploit their subjects than govern them,” and that “seeing that it was necessary to furnish good government to render the province peaceful and obedient to its lord,” Valentino appointed a stern and efficient administrator who “brought both unity and order.” One of the innovations Machiavelli admired most was Valentino’s formation of a citizen militia to serve alongside those grizzled professionals who made up the bulk of his forces. Watching a demonstration by these soldiers, n
attily attired in their gold and red uniforms—the Borgia heraldic colors—Machiavelli thought he saw a pale reflection of the armies of the Roman Republic that once had swept across the known world.
The man Valentino had appointed to govern his realm was Messer Remirro de Orca, who combined organizational skill with a sadistic streak that left a bloody trail across the Romagna. In praising Remirro (or Ramiro, as he is often called) and the man who employed him, Machiavelli reveals one of the pillars of his political philosophy: a preference for order over anarchy, even when that order was maintained by cruelty. Almost any atrocity could be justified if the end result was an improvement in the lives of the citizens who would be spared the random rapes, murders, and pillage that inevitably followed a breakdown of authority. Observing, as Savonarola had, a world descended into violence and wallowing in corruption, he drew radically different conclusions, based not on some vision of men miraculously transforming themselves into angels but on a hard-headed appraisal of the human animal. Machiavelli recognized, too, that in a dangerous world the greatest disasters were often the result of misplaced kindness. He had already seen how Florentine lenience in dealing with the feuding factions in Pistoia had permitted the bloody strife to continue year after year; if Valentino’s methods were more brutal, they were also more effective. “Cesare Borgia was considered cruel,” he writes in The Prince, “yet his cruelty brought an end to the disorders in the Romagna, uniting it in peace and loyalty. If this is considered good, one must judge him as much kinder than the Florentine people who, in order to escape being called cruel, allowed Pistoia to be destroyed.”
Machiavelli was willing to accept an effusion of blood if it resulted in a more orderly state, but he reserved his highest praise for those who achieved security through more subtle means. Thus what happened next greatly increased his admiration for the cunning Duke. Summoning Remirro to join him in Cesena, where he had paused with his army before heading to Sinigaglia, Valentino first set out a banquet for his lieutenant, apparently a reward for a job well done. Drowsy and relaxed, Remirro was completely unprepared when, at a signal from Valentino, armed men rushed into the hall and seized him. Both Machiavelli and the citizens were initially perplexed by this sudden turn of events, as, indeed, was Remirro, who insisted he had done nothing but faithfully serve his lord. But Machiavelli realized that Valentino’s apparently arbitrary about-face was actually a brilliant public relations coup: “no doubt [Remirro] will be sacrificed to satisfy the people, whose greatest wish is to see this done,” he explained to the Ten.
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