Of Niccolò’s early years and education little is known. His works show wide reading in the Latin and Italian classics, but it is almost certain that he had not mastered the Greek language. To the defects of Machiavelli’s education we may, in part at least, ascribe the peculiar vigour of his style and his speculative originality. He is free from the scholastic trifling and learned frivolity which tainted the rhetorical culture of his century. He made the world of men and things his study, learned to write his mother-tongue with idiomatic conciseness, and nourished his imagination on the masterpieces of the Romans.

The year of Charles VIII.’s invasion and of the Medici’s expulsion from Florence (1494) saw Machiavelli’s first entrance into public life. He was appointed clerk in the second chancery of the commune under his old master, the grammarian, Marcello Virgilio Adriani. Early in 1498 Adriani became chancellor of the republic, and Machiavelli received his vacated office with the rank of second chancellor and secretary. This post he retained till the year 1512. The masters he had to serve were the dieci di libertà e pace, who, though subordinate to the signoria, exercised a separate control over the departments of war and the interior. They sent their own ambassadors to foreign powers, transacted business with the cities of the Florentine domain, and controlled the military establishment of the commonwealth. The next fourteen years of Machiavelli’s life were fully occupied in the voluminous correspondence of his bureau, in diplomatic missions of varying importance, and in the organization of a Florentine militia. It would be tedious to follow him through all his embassies to petty courts of Italy, the first of which took place in 1499, when he was sent to negotiate the continuance of a loan to Catherine Sforza, countess of Forlì and Imola. In 1500 Machiavelli travelled into France, to deal with Louis XII. about the affairs of Pisa. These embassies were the school in which Machiavelli formed his political opinions, and gathered views regarding the state of Europe and the relative strength of nations. They not only introduced him to the subtleties of Italian diplomacy, but also extended his observation over races very different from the Italians. He thus, in the course of his official business, gradually acquired principles and settled ways of thinking which he afterwards expressed in writing.

In 1502 Machiavelli married Marietta Corsini, who bore him several children, with whom, in spite of his own infidelities, he lived on good terms, and who survived him twenty-six years. In the same year Piero Soderini was chosen gonfalonier for life, in accordance with certain changes in the constitution of the state, which were intended to bring Florence closer to the Venetian type of government. Machiavelli became intimately connected with Soderini, assisted him in carrying out his policy, suggested important measures of military reform which Soderini adopted, and finally was involved in ruin by his fall.

The year 1502 was marked by yet another decisive incident in Machiavelli’s life. In October he was sent, much against his will, as envoy to the camp of Cesare Borgia, duke of Valentinois. The duke was then in Romagna, and it was Machiavelli’s duty to wait upon and watch him. He was able now to observe those intricate intrigues which culminated in Cesare’s murder of his disaffected captains. From what remains of Machiavelli’s official letters, and from his tract upon the Modo che tenne il duca Valentino per ammazzar Vitellozzo Vitelli, we are able to appreciate the actual relations which existed between the two men, and the growth in Machiavelli’s mind of a political ideal based upon his study of the duke’s character. Machiavelli conceived the strongest admiration for Cesare’s combination of audacity with diplomatic prudence, for his adroit use of cruelty and fraud, for his self-reliance, avoidance of half-measures, employment of native troops, and firm administration in conquered provinces. More than once, in letters to his friend Vettori, no less than in the pages of the Principe, Machiavelli afterwards expressed his belief that Cesare Borgia’s behaviour in the conquest of provinces, the cementing of a new state out of scattered elements, and the dealing with false friends or doubtful allies, was worthy of all commendation and of scrupulous imitation. As he watched Cesare Borgia at this, the most brilliant period of his adventurous career, the man became idealized in his reflective but imaginative mind. Round him, as a hero, he allowed his own conceptions of the perfect prince to cluster. That Machiavelli separated the actual Cesare Borgia, whom he afterwards saw, ruined and contemptible, at Rome, from this radiant creature of his political fancy, is probable. That the Cesare of history does not exactly match the Duca Valentino of Machiavelli’s writings is certain. Still the fact remains that henceforth Machiavelli cherished the ideal image of the statesman which he had modelled upon Cesare, and called this by the name of Valentino.

On his return to Florence early in January 1503, Machiavelli began to occupy himself with a project which his recent attendance upon Cesare Borgia had strengthened in his mind. The duties of his office obliged him to study the conditions of military service as they then existed in Italy. He was familiar with the disadvantages under which republics laboured when they engaged professional captains of adventure and levied mercenary troops. The bad faith of the condottiere Paolo Vitelli (beheaded at Florence in 1499) had deeply impressed him. In the war with Pisa he had observed the insubordination and untrustworthiness of soldiers gathered from the dregs of different districts, serving under egotistical and irresponsible commanders. His reading in Livy taught him to admire the Roman system of employing armies raised from the body of the citizens; and Cesare Borgia’s method of gradually substituting the troops of his own duchy for aliens and mercenaries showed him that this plan might be adopted with success by the Italians. He was now determined, if possible, to furnish Florence with a national militia. The gonfalonier Soderini entered into his views. But obstacles of no small magnitude arose. The question of money was immediately pressing. Early in 1503 Machiavelli drew up for Soderini a speech, Discorso sulla provisione del danaro, in which the duty and necessity of liberal expenditure for the protection of the state were expounded upon principles of sound political philosophy. Between this date and the last month of 1506 Machiavelli laboured at his favourite scheme, working out memorials on the subject for his office, and suggesting the outlines of a new military organization. On the 6th of December 1506 his plan was approved by the signoria, and a special ministry, called the nove di ordinanza e milizia, was appointed. Machiavelli immediately became their secretary. The country districts of the Florentine dominion were now divided into departments, and levies of foot soldiers were made in order to secure a standing militia. A commander-in-chief had to be chosen for the new troops. Italian jealousy shrank from conferring this important office on a Florentine, lest one member of the state should acquire a power dangerous to the whole. The choice of Soderini and Machiavelli fell, at this juncture, upon an extremely ineligible person, none other than Don Micheletto, Cesare Borgia’s cut-throat and assassin. It is necessary to insist upon this point, since it serves to illustrate a radical infirmity in Machiavelli’s genius. While forming and promoting his scheme, he was actuated by principles of political wisdom and by the purest patriotism. But he failed to perceive that such a ruffian as Micheletto could not inspire the troops of Florence with that devotion to their country and that healthy moral tone which should distinguish a patriot army. Here, as elsewhere, he revealed his insensibility to the ethical element in human nature.

Meanwhile Italy had been the scene of memorable events, in most of which Machiavelli took some part. Alexander VI. had died suddenly of fever. Julius II. had ascended the papal chair. The duke of Valentinois had been checked in mid-career of conquest. The collapse of the Borgias threw Central Italy into confusion; and Machiavelli had, in 1505, to visit the Baglioni at Perugia and the Petrucci at Siena. In the following year he accompanied Julius upon his march through Perugia into the province of Emilia, where the fiery pope subdued in person the rebellious cities of the Church. Upon these embassies Machiavelli represented the Florentine dieci in quality of envoy. It was his duty to keep the ministry informed by means of frequent despatches and reports. All this while the war for the recovery of Pisa was slowly dragging on, with no success or honour to the Florentines. Machiavelli had to attend the camp and provide for levies amid his many other occupations. And yet he found time for private literary work. In the autumn of 1504 he began his Decennali, or Annals of Italy, a poem composed in rough terza rima. About the same time he composed a comedy on the model of Aristophanes, which is unfortunately lost. It seems to have been called Le Maschere. Giuliano de’ Ricci tells us it was marked by stringent satire upon great ecclesiastics and statesmen, no less than by a tendency to “ascribe all human things to natural causes or to fortune.” That phrase accurately describes the prevalent bias of its author’s mind.

The greater part of 1506 and 1507 was spent in organizing the new militia, corresponding on the subject, and scouring the country on enlistment service. But at the end of the latter year European affairs of no small moment diverted Machiavelli from these humbler duties. Maximilian was planning a journey into Italy in order to be crowned emperor at Rome, and was levying subsidies from the imperial burghs for his expenses. The Florentines thought his demands excessive. Though they already had Francesco Vettori at his court, Soderini judged it advisable to send Machiavelli thither in December. He travelled by Geneva, all through Switzerland, to Botzen, where he found the emperor. This journey was an important moment in his life. It enabled him to study the Swiss and the Germans in their homes; and the report which he wrote on his return is among his most effective political studies. What is most remarkable in it is his concentrated effort to realize the exact political weight of the German nation, and to penetrate the causes of its strength and weakness. He attempts to grasp the national character as a whole, and thence to deduce practical conclusions. The same qualities are noticeable in his Ritratti delle cose di Francia, which he drew up after an embassy to Louis XII. at Blois in 1510. These notes upon the French race are more scattered than the report on German affairs. But they reveal no less acumen combined with imaginative penetration into the very essence of national existence.

Machiavelli returned from Germany in June 1508. The rest of that year and a large part of 1509 were spent in the affairs of the militia and the war of Pisa. Chiefly through his exertions the war was terminated by the surrender of Pisa in June 1509. Meanwhile the league of Cambray had disturbed the peace of Italy, and Florence found herself in a perilous position between Spain and France. Soderini’s government grew weaker. The Medicean party lifted up its head. To the league of Cambray succeeded the Holy League. The battle of Ravenna was fought, and the French retired from Italy. The Florentines had been spectators rather than actors in these great events. But they were now destined to feel the full effects of them. The cardinal Giovanni de’ Medici, who was present at the battle of Ravenna, brought a Spanish army into Tuscany. Prato was sacked in the August of 1512. Florence, in extreme terror, deposed the gonfalonier, and opened her gates to the princes of the house of Medici.

The government on which Machiavelli depended had fallen, never to rise again. The national militia in which he placed unbounded confidence had proved inefficient to protect Florence in the hour of need. He was surrounded by political and personal enemies, who regarded him with jealousy as the ex-gonfalonier’s right-hand man. Yet at first it appears that he still hoped to retain his office. He showed no repugnance to a change of masters, and began to make overtures to the Medici. The nove della milizia were, however, dissolved; and on the 7th of November 1512 Machiavelli was deprived of his appointments. He was exiled from Florence and confined to the dominion for one year, and on the 17th of November was further prohibited from setting foot in the Palazzo Pubblico. Ruin stared him in the face; and, to make matters worse, he was implicated in the conspiracy of Pier Paolo Boscoli in February 1513. Machiavelli had taken no share in that feeble attempt against the Medici, but his name was found upon a memorandum dropped by Boscoli. This was enough to ensure his imprisonment. He was racked, and only released upon Giovanni de’ Medici’s election to the papacy in March 1513. When he left his dungeon he retired to a farm near San Casciano, and faced the fact that his political career was at an end.

Machiavelli now entered upon a period of life to which we owe the great works that have rendered his name immortal. But it was one of prolonged disappointment and annoyance. He had not accustomed himself to economical living; and, when the emoluments of his office were withdrawn, he had barely enough to support his family. The previous years of his manhood had been spent in continual activity. Much as he enjoyed the study of the Latin and Italian classics, literature was not his business; nor had he looked on writing as more than an occasional amusement. He was now driven in upon his books for the employment of a restless temperament; and to this irksomeness of enforced leisure may be ascribed the production of the Principe, the Discorsi, the Arte della guerra, the comedies, and the Historie fiorentine. The uneasiness of Machiavelli’s mind in the first years of this retirement is brought before us by his private correspondence. The letters to Vettori paint a man of vigorous intellect and feverish activity, dividing his time between studies and vulgar dissipations, seeking at one time distraction in low intrigues and wanton company, at another turning to the great minds of antiquity for solace. It is not easy to understand the spirit in which the author of the Principe sat down to exchange obscenities with the author of the Sommario della storia d’Italia. At the same time this coarseness of taste did not blunt his intellectual sagacity. His letters on public affairs in Italy and Europe, especially those which he meant Vettori to communicate to the Medici at Rome, are marked by extraordinary fineness of perception, combined, as usual in his case, with philosophical breadth. In retirement at his villa near Percussina, a hamlet of San Casciano, Machiavelli completed the Principe before the end of 1513. This famous book is an analysis of the methods whereby an ambitious man may rise to sovereign power. It appears to have grown out of another scarcely less celebrated work, upon which Machiavelli had been engaged before he took the Principe in hand, and which he did not finish until some time afterwards. This second treatise is the Discorsi sopra la prima deca di Tito Livio.