Machiavelli was born in a tumultuous era — popes waged acquisitive wars against Italian city - states, and people and cities might fall from power at any time. Along with the pope and the major cities like Venice and Florence, foreign powers such as France, Spain, the Holy Roman Empire, and even Switzerland battled for regional influence and control. Political - military alliances continually changed, featuring condottieri (mercenary leaders) who changed sides without warning, and short lived governments rising and falling.

Machiavelli was taught grammar, rhetoric, and Latin, and became a magnificent writer. It is thought that he did not learn Greek, even though Florence was at the time one of the centers of Greek scholarship in Europe. In 1494, Florence restored the republic — expelling the Medici family, who had ruled Florence for some sixty years. In June 1498, shortly after the execution of Savonarola, Machiavelli, at the age of 29, was elected as head of the second chancery. In July 1498, he was also made the secretary of the Dieci di Libertà e Pace. He was in a diplomatic council responsible for negotiation and military affairs, carrying out, between 1499 and 1512, several diplomatic missions, to the court of Louis XII in France; to that of Ferdinand II of Aragón, in Spain; in Germany; and to the Papacy in Rome, in the Italian states. Moreover, from 1502 to 1503, he witnessed the brutal reality of the state - building methods of Cesare Borgia (1475 – 1507), and his father Pope Alexander VI, who were then engaged in the process of trying to bring a large part of central Italy under their possession, partly under the pretext of defending Church interests.

Between 1503 and 1506, Machiavelli was responsible for the Florentine militia, including the City’s defense. He distrusted mercenaries (a distrust he explained in his official reports, and then later in his theoretical works), preferring a politically invested citizen - militia - a philosophy that bore fruit. His command of Florentine citizen - soldiers defeated Pisa in 1509; yet, in August of 1512, the Medici, helped by Pope Julius II, used Spanish troops to defeat the Florentines at Prato. Piero Soderini resigned as Florentine head of state, and left in exile. The Florentine city - state and the Republic were dissolved. Machiavelli was deprived of office in 1512 by the Medici, and, in 1513, was accused of conspiracy, and arrested and imprisoned for a time. Despite torture ("with the rope", where the prisoner is hanged from his bound wrists, from the back, forcing the arms to bear the body's weight, thus dislocating the shoulders), he denied involvement and was released; then, retiring to his estate, at Sant' Andrea in Percussina, near San Casciano in Val di Pesa, he devoted himself to study and writing the political treatises that earned his intellectual place in the development of political philosophy and political conduct. Despairing of the opportunity to remain directly involved in political matters, after a time Machiavelli began to participate in intellectual groups in Florence and wrote several plays that (unlike his works on politics / political theory) were both popular and widely known in his lifetime. Still politics remained his main passion and to satisfy interest he maintained a well known correspondence with better politically connected friends, attempting to become involved once again in political life.

In a letter to Francesco Vettori, he described his exile:

When evening comes, I return home and go to my study. On the threshold, I strip naked, taking off my muddy, sweaty work day clothes, and put on the robes of court and palace, and, in this graver dress, I enter the courts of the ancients, and am welcomed by them, and there I taste the food that alone is mine, and for which I was born. And there I make bold to speak to them and ask the motives of their actions, and they, in their humanity, reply to me. And for the space of four hours I forget the world, remember no vexation, fear poverty no more, tremble no more at death; I pass indeed into their world.

Machiavelli died in 1527 at the age of 58. He was buried at the Church of Santa Croce in Florence, Italy. An epitaph honoring him is inscribed in a small monument. The Latin legend reads: TANTO NOMINI NULLUM PAR ELOGIUM ("so great a name (has) no adequate praise" or "no eulogy (would be) appropriate to (praise) such a great name").

Machiavelli’s best known book, Il Principe, contains a number of maxims concerning politics, but rather than the more traditional subject of a hereditary prince, it concentrates on the possibility of a "new prince". To retain power, the hereditary prince must carefully maintain the socio - political institutions to which the people are accustomed; whereas a new prince has the more difficult task in ruling, since he must first stabilize his new - found power in order to build an enduring political structure. He believed that social benefits of stability and security could be achieved in the face of moral corruption. Aside from that, Machiavelli believed that public and private morality had to be separate in order to rule. That required the prince being concerned with reputation but also being willing to act immorally. As a political scientist, Machiavelli emphasizes the occasional need for the methodical exercise of brute force, deceit, and so on.

Notwithstanding some mitigating themes, the Catholic Church proscribed The Prince, registering it to the Index Librorum Prohibitorum, and humanists also viewed the book negatively — among them, Erasmus of Rotterdam. As a treatise, its primary intellectual contribution to the history of political thought is the fundamental break between political Realism and political Idealism — thus, The Prince is a manual to acquiring and keeping political power. In contrast with Plato and Aristotle, Machiavelli insisted that an imaginary ideal society is not the model for a prince to orient himself by.

Concerning the differences and similarities in Machiavelli's advice to ruthless and tyrannical princes in The Prince and his more republican exhortations in Discourses on Livy, many have concluded that The Prince although written in the form of advice for a monarchical prince, contains arguments for the superiority of republican regimes, similar to those found in the Discourses. In the 18th century the work was even called a satire, for example by Jean - Jacques Rousseau. More recently, commentators such as Leo Strauss and Harvey Mansfield have agreed that the Prince can be read as having a deliberate comical irony. Other commentators have not seen the irony as deliberate comedy, but most commentators agree that the Prince is in any case republican to some extent.

Antonio Gramsci argued that Machiavelli's audience for this work was not even the ruling class but the common people because the rulers already knew these methods through their education.

The Discourses on the First Ten Books of Titus Livy (Discorsi) nominally discuss a classical history of early Ancient Rome. Machiavelli presents it as a series of lessons on how a republic should be started and structured. It is a larger work than the Prince, and it more openly explains the advantages of republics. It includes early versions of the concept of checks and balances, and asserts the superiority of a republic over a principality. It became one of the central texts of republicanism.

From The Discourses:

• “In fact, when there is combined under the same constitution a prince, a nobility, and the power of the people, then these three powers will watch and keep each other reciprocally in check”. Book I, Chapter II
• “Doubtless these means [of attaining power] are cruel and destructive of all civilized life, and neither Christian, nor even human, and should be avoided by every one. In fact, the life of a private citizen would be preferable to that of a king at the expense of the ruin of so many human beings”. Book I, Chapter XXVI
• “Now, in a well - ordered republic, it should never be necessary to resort to extra - constitutional measures. . . . ” Book I, Chapter XXXIV
• “. . . the governments of the people are better than those of princes”. Book I, Chapter LVIII
• “. . . if we compare the faults of a people with those of princes, as well as their respective good qualities, we shall find the people vastly superior in all that is good and glorious”. Book I, Chapter LVIII
• “For government consists mainly in so keeping your subjects that they shall be neither able, nor disposed to injure you. . . . ” Book II, Chapter XXIII
• “. . . no prince is ever benefited by making himself hated”. Book III, Chapter XIX
• “Let not princes complain of the faults committed by the people subjected to their authority, for they result entirely from their own negligence or bad example”. Book III, Chapter XXIX

• Discorso sopra le cose di Pisa (1499)
• Del modo di trattare i popoli della Valdichiana ribellati (1502)
• Del modo tenuto dal duca Valentino nell’ ammazzare Vitellozzo Vitelli, Oliverotto da Fermo, etc. (1502) — A Description of the Methods Adopted by the Duke Valentino when Murdering Vitellozzo Vitelli, Oliverotto da Fermo, the Signor Pagolo, and the Duke di Gravina Orsini
• Discorso sopra la provisione del danaro (1502) — A discourse about the provision of money.
• Ritratti delle cose dell’ Alemagna (1508–1512) - Portrait of the affairs of Germany.
• Dell’Arte della Guerra (1519–1520) — The Art of War, high military science.
• Discorso sopra il riformare lo stato di Firenze (1520) — A discourse about the reforming of Florence.
• Sommario delle cose della citta di Lucca (1520) — A summary of the affairs of the city of Lucca.
• The Life of Castruccio Castracani of Lucca(1520) — Vita di Castruccio Castracani da Lucca, a short biography.
• Istorie Florentine (1520 – 1525) — Florentine Histories, an eight - volume history book of the city - state, Florence, commissioned by Giulio di Giuliano de’ Medici, later Pope Clement VII.

Besides being a statesman and political scientist, Machiavelli also translated classical works, and was a dramaturge (Clizia, Mandragola), a poet (Sonetti, Canzoni, Ottave, Canti carnascialeschi), and a novelist (Belfagor arcidiavolo).

Some of his other work:

• Decennale primo (1506), a poem in terza rima.
• Decennale secondo (1509), a poem.
• Ritratti delle cose di Francia (1510) — Portrait of the affairs of France.
• Andria or The Woman of Andros (1517), a Classical comedy, translated from Terence.
• Mandragola (1518) — The Mandrake, a five - act prose comedy, with a verse prologue.
• Clizia (1525), a prose comedy.
• Belfagor arcidiavolo (1515), a novel.
• Asino d’oro (1517) — The Golden Ass is a terza rima poem, a new version of the Classic work by Apuleius.
• Frammenti storici (1525) — Fragments of stories.

Della lingua (1514), a dialogue about the language is also normally considered to be by Machiavelli.

Machiavelli's literary executor, Giuliano de'Ricci, also reported having seen that Machiavelli, his grandfather, made a comedy in the style of Aristophanes which included living Florentines as characters, and to be titled Le Maschere. It has been suggested that due to such things as this and his style of writing to his superiors generally, there was very likely some animosity to Machiavelli even before the return of the Medici.

Commentators have taken very different approaches to Machiavelli, and not always agreed. Major discussion has tended to be especially about two issues, first how unified and philosophical his work is, and secondly concerning how innovative or traditional it is.

There is some disagreement concerning how best to describe the unifying themes, if there are any, that can be found in Machiavelli's works, especially in the two major political works, The Prince and Discourses. Some commentators have described him as inconsistent, and perhaps as not even putting a high priority in consistency. Others such as Hans Baron have argued that his ideas must have changed dramatically over time. Some have argued that his conclusions are best understood as a product of his times, experiences and education. Others, such as Leo Strauss and Harvey Mansfield, have argued strongly that there is a very strong and deliberate consistency and distinctness, even arguing that this extends to all of Machiavelli's works including his comedies and letters.

Commentators such as Leo Strauss have gone so far as to name Machiavelli as the deliberate originator of modernity itself. Others have argued that Machiavelli is only a particularly interesting example of trends which were happening around him. In any case Machiavelli presented himself at various times as someone reminding Italians of the old virtues of the Romans and Greeks, and other times as someone promoting a completely new approach to politics.

That Machiavelli had a wide range of influences is in itself not controversial. Their relative importance is however a subject of ongoing discussion. It is possible to summarize some of the main influences emphasized by different commentators.

1. The Mirror of Princes genre. Gilbert (1938) summarized the similarities between The Prince and the genre it obviously imitates, the so called "Mirror of Princes" style. This was a classically influenced genre, with models at least as far back as Xenophon and Isocrates, that was still quite popular during Machiavelli's life. While Gilbert emphasizes the similarities however, he agrees with all other commentators that Machiavelli was particularly novel in the way he used this genre, even when compared to his contemporaries such as Baldassare Castiglione and Erasmus. One of the major innovations Gilbert noted was that Machiavelli focused upon the "deliberate purpose of dealing with a new ruler who will need to establish himself in defiance of custom". Normally, these types of works were addressed only to hereditary princes.

2. Classical republicanism. Commentators such as Quentin Skinner and J.G.A. Pocock, in the so called "Cambridge School" of interpretation have been able to show that some of the republican themes in Machiavelli's political works, particularly the Discourses on Livy, can be found in medieval Italian literature which was influenced by classical authors such as Sallust.

3. Classical political philosophy: Xenophon, Plato and Aristotle. The Socratic school of classical political philosophy, especially Aristotle, had become a major influence upon European political thinking in the late Middle Ages. It existed both in the catholicized form presented by Thomas Aquinas, and in the more controversial "Averroist" form of authors like Marsilius of Padua. Machiavelli was critical of catholic political thinking and may have been influenced by Averroism. But he cites Plato and Aristotle very infrequently and apparently did not approve of them. Leo Strauss argued that the strong influence of Xenophon, a student of Socrates more known as an historian, rhetorician and soldier, was a major source of Socratic ideas for Machiavelli, sometimes not in line with Aristotle. While interest in Plato was increasing in Florence during Machiavelli's lifetime he also does not show particular interest in him, but was indirectly influenced by his readings of authors such as Polybius, Plutarch and Cicero.

The major difference between Machiavelli and the Socratics, according to Strauss, is Machiavelli's materialism and therefore his rejection of both a teleological view of nature, and of the view that philosophy is higher than politics. Aimed - for things which the Socratics argued would tend to happen by nature, Machiavelli said would happen by chance.

4. Classical materialism. Strauss argued that Machiavelli may have seen himself as influenced by some ideas from classical materialists such as Democritus, Epicurus and Lucretius. Strauss however sees this also as a sign of major innovation in Machiavelli, because classical materialists did not share the Socratic regard for political life, while Machiavelli clearly did.

5. Thucydides. Some scholars note the similarity between Machiavellian and the Greek historian Thucydides, since both emphasized power politics. Strauss argued that Machiavelli may indeed have been influenced by pre-Socratic philosophers, but he felt it was a new combination:-

...contemporary readers are reminded by Machiavelli’s teaching of Thucydides; they find in both authors the same “realism,” i.e., the same denial of the power of the gods or of justice and the same sensitivity to harsh necessity and elusive chance. Yet Thucydides never calls in question the intrinsic superiority of nobility to base ness, a superiority that shines forth particularly when the noble is destroyed by the base. Therefore Thucydides’ History arouses in the reader a sadness which is never aroused by Machiavelli’s books. In Machiavelli we find comedies, parodies, and satires but nothing reminding of tragedy. One half of humanity remains outside of his thought. There is no tragedy in Machiavelli because he has no sense of the sacredness of “the common.” — Strauss (1958)

Amongst commentators, there are a few consistently made proposals concerning what was most new in Machiavelli's work.

Machiavelli is sometimes seen as the prototype of a modern empirical scientist, building generalizations from experience and historical facts, and emphasizing the uselessness of theorizing with the imagination.

Machiavelli studied the way people lived and aimed to inform leaders how they should rule and even how they themselves should live. For example, Machiavelli denies that living virtuously necessarily leads to happiness. And Machiavelli viewed misery as one of the vices that enables a prince to rule. Machiavelli stated that it would be best to be both loved and feared. But since the two rarely come together, anyone compelled to choose will find greater security in being feared than in being loved. In much of Machiavelli's work, it seems that the ruler must adopt unsavory policies for the sake of the continuance of his regime.

A related and more controversial proposal often made is that he described how to do things in politics in a way which seemed neutral concerning who used the advice - tyrants or good rulers.

That Machiavelli strove for realism is not doubted, but for four centuries scholars have debated how best to describe his morality. The Prince made the word "Machiavellian" a byword for deceit, despotism, and political manipulation. That Machiavelli himself was not evil and indeed intended good, is on the other hand generally accepted.

Leo Strauss, an American political philosopher, declared himself more inclined toward the traditional view that Machiavelli was self - consciously a "teacher of evil," (even if he was not himself evil) since he counsels the princes to avoid the values of justice, mercy, temperance, wisdom, and love of their people in preference to the use of cruelty, violence, fear, and deception. Italian anti - fascist philosopher Benedetto Croce (1925) concludes Machiavelli is simply a "realist" or "pragmatist" who accurately states that moral values in reality do not greatly affect the decisions that political leaders make. German philosopher Ernst Cassirer (1946) held that Machiavelli simply adopts the stance of a political scientist — a Galileo of politics — in distinguishing between the "facts" of political life and the "values" of moral judgment.

Machiavelli is generally seen as being critical of Christianity as it existed in his time, specifically its effect upon politics, and also everyday life. In his opinion, Christianity, along with teleological Aristotelianism that the church had come to accept, allowed practical decisions to be guided too much by imaginary ideals and encouraged people to lazily leave events up to providence or, as he would put it, chance, luck or fortune. While Christianity sees modesty as a virtue and pride as sinful, Machiavelli took a more classical position, seeing ambition, spiritedness, and the pursuit of glory as good and natural things, and part of the virtue and prudence that good princes should have. Therefore, while it was traditional to say that leaders should have virtues, especially prudence, Machiavelli's use of the words virtù and prudenza was unusual for his time, implying a spirited and immodest ambition. Famously, Machiavelli argued that virtue and prudence can help a man control more of his future, in the place of allowing fortune to do so.

Najemy (1993) has argued that this same approach can be found in Machiavelli's approach to love and desire, as seen in his comedies and correspondence. Najemy shows how Machiavelli's friend Vettori argued against Machiavelli and cited a more traditional understanding of fortune.

On the other hand, humanism in Machiavelli's time meant that classical pre - Christian ideas about virtue and prudence, including the possibility of trying to control one's future, were not unique to him. But humanists did not go so far as to promote the extra glory of deliberately aiming to establish a new state, in defiance of traditions and laws.

While Machiavelli's approach had classical precedents, it has been argued that it did more than just bring back old ideas, and that Machiavelli was not a typical humanist. Strauss (1958) argues that the way Machiavelli combines classical ideas is new. While Xenophon and Plato also described realistic politics, and were closer to Machiavelli than Aristotle was, they, like Aristotle, also saw Philosophy as something higher than politics. Machiavelli was apparently a materialist who objected to explanations involving formal and final causation, or teleology.

Machiavelli's promotion of ambition amongst leaders while denying any higher standard meant that he encouraged risk taking, and innovation, most famously the founding of new modes and orders. His advice to prince was therefore certainly not limited to discussing how to maintain a state. It has been argued that Machiavelli's promotion of innovation led directly to the argument for progress as an aim of politics and civilization. But while a belief that humanity can control its own future, control nature, and "progress" has been long lasting, Machiavelli's followers, starting with his own friend Guicciardini, have tended to prefer peaceful progress through economic development, and not warlike progress. As Harvey Mansfield (1995) wrote: "In attempting other, more regular and scientific modes of overcoming fortune, Machiavelli's successors formalized and emasculated his notion of virtue."

Machiavelli however, along with some of his classical predecessors, saw ambition and spiritedness, and therefore war, as inevitable and part of human nature.

Strauss concludes his 1958 Thoughts on Machiavelli by proposing that this promotion of progress leads directly to the modern arms race. Strauss argued that the unavoidable nature of such arms races, which have existed before modern times and led to the collapse of peaceful civilizations, provides us with both an explanation of what is most truly dangerous in Machiavelli's innovations, but also the way in which the aims of his apparently immoral innovation can be understood.

Machiavelli explains repeatedly that religion is man-made, and that the value of religion lies in its contribution to social order and the rules of morality must be dispensed with if security required it. In The Prince, the Discourses, and in the Life of Castruccio Castracani, he describes "prophets", as he calls them, like Moses, Romulus, Cyrus the Great, and Theseus (he treats pagan and Christian patriarchs in the same way) as the greatest of new princes, the glorious and brutal founders of the most novel innovations in politics, and men who Machiavelli assures us have always used a large amount of armed force and murder against their own people. He estimated that these sects last from 1666 to 3000 years each time, which, as pointed out by Leo Strauss, would mean that Christianity became due to start finishing about 150 years after Machiavelli. Machiavelli's concern with Christianity as a sect was that it makes men weak and inactive, delivering politics into the hands of cruel and wicked men without a fight.

While fear of God can be replaced by fear of the prince, if there is a strong enough prince, Machiavelli felt that having a religion is in any case especially essential to keeping a republic in order. For Machiavelli, a truly great prince can never be conventionally religious himself, but he should make his people religious if he can. According to Strauss (1958) he was not the first person to ever explain religion in this way, but his description of religion was novel because of the way he integrated this into his general account of princes.

Machiavelli's judgment that democracies need religion for practical political reasons was widespread amongst modern proponents of republics until approximately the time of the French revolution. This therefore represents a point of disagreement between himself and late modernity.

Despite the classical precedents, which Machiavelli was not the only one to promote in his time, Machiavelli's realism and willingness to argue that good ends justify bad things, is seen as a critical stimulus towards some of the most important theories of modern politics.

Firstly, particularly in the Discourses on Livy, Machiavelli is unusual in the positive side he sometimes seems to describe in factionalism in republics. For example quite early in the Discourses, (in Book I, chapter 4), a chapter title announces that the disunion of the plebs and senate in Rome "kept Rome free". That a community has different components whose interests must be balanced in any good regime is an idea with classical precedents, but Machiavelli's particularly extreme presentation is seen as a critical step towards the later political ideas of both a division of powers or checks and balances, ideas which lay behind the US constitution (and most modern constitutions).

Similarly, the modern economic argument for capitalism, and most modern forms of economics, was often stated in the form of "public virtue from private vices". Also in this case, even though there are classical precedents, Machiavelli's insistence on being both realistic and ambitious, not only admitting that vice exists but being willing to risk encouraging it, is a critical step on the path to this insight.

Mansfield however argues that Machiavelli's own aims have not been shared by those influenced by him. Machiavelli argued against seeing mere peace and economic growth as worthy aims on their own, if they would lead to what Mansfield calls the "taming of the prince".

Machiavelli is most famous for a short political treatise, The Prince, written in 1513 but not published until 1532, five years after his death. Although he privately circulated The Prince among friends, the only theoretical work to be printed in his lifetime was The Art of War, about military science. Since the 16th century, generations of politicians remain attracted and repelled by its apparently neutral acceptance, or even positive encouragement, of the immorality of powerful men, described especially in The Prince but also in his other works.

His works are sometimes even said to have contributed to the modern negative connotations of the words politics and politician, and it is sometimes thought that it is because of him that Old Nick became an English term for the Devil and the adjective Machiavellian became a pejorative term describing someone who aims to deceive and manipulate others for personal advantage. Machiavellianism also remains a popular term used in speeches and journalism; while in psychology, it denotes a personality type.

While Machiavellianism is notable in the works of Machiavelli, Machiavelli's works are complex and he is generally agreed to have been more than just "Machiavellian" himself. For example, J.G.A. Pocock (1975) saw him as a major source of the republicanism that spread throughout England and North America in the 17th and 18th centuries and Leo Strauss (1958), whose view of Machiavelli is quite different in many ways, agreed about Machiavelli's influence on republicanism and argued that even though Machiavelli was a teacher of evil he had a nobility of spirit that led him to advocate ignoble actions. Whatever his intentions, which are still debated today, he has become associated with any proposal where "the end justifies the means". For example Leo Strauss (1958) wrote:

Machiavelli is the only political thinker whose name has come into common use for designating a kind of politics, which exists and will continue to exist independently of his influence, a politics guided exclusively by considerations of expediency, which uses all means, fair or foul, iron or poison, for achieving its ends - its end being the aggrandizement of one's country or fatherland - but also using the fatherland in the service of the self - aggrandizement of the politician or statesman or one's party.