Life
Niccolo Machiavelli was born in Florence in 1469. The return of the Medici in 1512 overthrew Soderini’s republic and caused Machiavelli both the loss of his position and even brief imprisonment for his republican sympathies. The Prince was written in 1513 but not published until after Machiavelli’s death, in 1513. (The Prince - Niccolo Machiavelli - Oxford p.0)

The Machiavelli had been a prominent Florentine family. In a letter to Francesco Vettori ‘I was born in poverty, and at an early age learned how to script rather than to thrive.’ (The Prince - Niccolo Machiavelli - Oxford p.ix)

Between 1499 and 1512 Machiavelli had the opportunity to meet the most important political leaders of his time:  the King of France, Louis XII; Emperor Maximilian I; Pope Julius II; and Duke Valentino (Cesare Borgia).  (The Prince - Niccolo Machiavelli - Oxford p.xi)

Maquiave;l ‘I love my native city more than my own soul’. (The Prince - Nicoolo Machiavelli - Oxfrod p.xxxix)

Why he wrote The Prince
The truth is that Machiavelli did try to obtain a position from the Medici, but he did not write The Prince in order to win their favor. He was hoping to be offered a new post in recognition of his unquestionable competence in the ‘art of the state’ and as a reward for his abilities and impeccable honesty, not as a gift in reward for flattery. As he wrote in the famous letter to Francesco Vettori of 10 December 1513. (The Prince - Niccolo Machiavelli - Oxford p.xiii)

Maquavel was extremely hostile to tyranny. Therefore he did not help the tyrant; his intention was not to instruct the tyrant, but by making all his secrets clear and openly displaying the degree of wretchedness to the people... while appearing to instruct the prince he was actually educating the people. (The Prince - Niccolo Machiavelli - Oxford p.xix)

The simple truth is that Machiavelli did not compose The Prince to sustain a political transition from a republic to a principality but to instruct a founder of a new military and political order and a redeemer of Italy, as I have already indicated. Even if Machiavelli, in The Prince and elsewhere, indicates that the people can be the prince, he believes that the work of foundation and redemption can be carried out by one man alone. (The Prince - Niccolo Machiavelli - Oxford p.xxi)

Critics 
‘wise man’, writes Spinoza, ‘seem to be particularly attractive in view of the well-known fact that he was an advocate of freedom, and also gave some very sound advice for preserving it’. (The Prince - Niccolo Machiavelli - Oxford p.xx)

Pierre Bayle’s Dictionnaire, and by Diderot in the Encyclopedie (‘it was the fault of his contemporaries if they misunderstood what he was getting at they took a satire for a eulogy) (The Prince - Niccolo Machiavelli - Oxford p.xx)
 
 
A new prince. 
A new prince must always harm his new subjects, both with his soldiers as well as with countless other injuries involved in his new conquest. Thus, you have made enemies of all those you harmed in occupying the principality, and you are unable to maintain as friends those who helped you to rise to power since you cannot satisfy them in the way that they had supposed. (The Prince - Niccolo Machiavelli - Oxford p.8)


Reputation
 
Avoid
That nothing is so unhealthy or unstable as the reputation for power that is not based upon one’s own forces. (The Prince - Niccolo Machiavelli - Oxford p.50)

Avoid neutrality
It will always happen that a friend will request your neutrality, and he who is your friend will ask you to disclose your intentions by taking up arms. In order to avoid present dangers, irresolute princes follow the neutral path most of the time, and most of the time they come to ruin. (The Prince - Niccolo Machiavelli - Oxford p.77)

A despised prince
What makes him despised is being considered changeable, frivolous, effeminate, cowardly, and irresolute. From these qualities, a prince must guard himself as if from a reef, and he must strive to make everyone recognize in his actions greatness, spirit, dignity, and strength. (The Prince - Niccolo Machiavelli - Oxford p.63)

Bad Fortune is bliss for reputation
Without a doubt, the prince becomes great when they overcome difficulties and obstacles imposed upon them. And therefore, Fortune - especially when she wishes to increase the reputation of a new prince, who has a greater need to acquire reputation than a hereditary prince does - creates enemies for him, and has them undertake enterprises against him so that he will have the chance to overcome them and to climb higher up the ladder his enemies have brought him. (The Prince - Niccolo Machiavelli - Oxford p.74)

The desirable reputation
And above all, a prince should strive in all of his actions to achieve the reputation of a great man of outstanding intelligence. (The Prince - Niccolo Machiavelli - Oxford p.77)

Have a stance
A prince is also respected when he is a true friend and a true enemy: that is when he declares himself to be on the side of one prince against another, without reserve. (The Prince - Niccolo Machiavelli - Oxford p.77)

Be prudent 
Prudence consists of knowing how to recognize the nature of disadvantages, and how to choose the least sorry one as good. (The Prince - Niccolo Machiavelli - Oxford p.78)

And learn how not to be good
A man who wishes to profess goodness at all times will come to ruin among so many who are not good. Therefore, it is necessary for a prince who wishes to maintain himself to learn how not to be good and to use this knowledge or not to use it according to necessity. (The Prince - Niccolo Machiavelli - Oxford p.53)

Types

Generous
There is nothing that uses itself up faster than generosity; for as you employ it, you lose the means of employing it, and you become rapacious and hated. (...) So it is wiser to live with the reputation of a miser, which gives birth to infamy without hatred than to be forced to incur the reputation of rapacity because you want to be considered generous, which gives birth to infamy with hatred. (The Prince - Niccolo Machiavelli - Oxford p.56)

Merciful
Turning to the other qualities mentioned above, let me say that every prince must desire to be considered merciful and not cruel: nevertheless, he must take care not to use such mercy badly. (The Prince - Niccolo Machiavelli - Oxford p.57)

Right Balance of mercy and cruelty
With a very few examples of cruelty, he will prove more compassionate than those who, out of excessive mercy, permit disorders to continue from which arise murders while the executions ordered by the prince injure specific individuals. (The Prince - Niccolo Machiavelli - Oxford p.57)

Feared or loved?
Whether it is better to be loved than to be feared, or the contrary. The answer is that one would like to be both one and the other. (The Prince - Niccolo Machiavelli - Oxford p.57)

Why?
But since it is difficult to both together, it is much safer to be feared than to be loved, when one of the two must be lacking. For one can generally say this about men: they are ungrateful, fickle, simulators and deceivers, avoiders of danger, and greedy for grain. While you work for their benefit they are completely your, offering you their blood, their property, their lives, and their sons, as I said above, when the need to do so is far away. But when it draws nearer to you, they turn away. The prince who relies entirely upon their words comes to ruin, finding himself stripped naked of other preparations. For friendships acquired by a price and not owned, and at the proper time cannot be spent. Men are less hesitant about injuring someone who makes himself loved than one who makes himself feared because love is held together by a chain of obligation that, since men are a wretched lot, is broken on every occasion for their own self-interest; but fear is sustained by a dread of punishment that will never abandon you. (The Prince - Niccolo Machiavelli - Oxford p.58)

Ok, be feard but avoid hate.
A prince must nevertheless make himself feared in such a way that he will avoid hatred, even if he does not acquire love; since one can very easily be feared and yet not be hated. (...) for men forget the death of their father more quickly than the loss of their patrimony. (The Prince - Niccolo Machiavelli - Oxford p.58)

How to avoid being hated then?
Hate: He must refrain from this. In most cases, so long as you do not deprive them of either their honor or their property, most men live content, and you only have to contend with the ambition of the few, who can be restrained without difficulty and by any means. (The Prince - Niccolo Machiavelli - Oxford p.63)

But if I can’t be avoided being hated?
Since princes cannot avoid being hated by somebody, they must first seek not to be hated by the largest group. When they cannot do this, they must try with every effort to avoid the hatred of the most powerful group. (The Prince - Niccolo Machiavelli - Oxford p.64

An example of the fear that worked 
Numbered among the remarkable deeds of Hannibal is this: that while he had a very large army made up of all kinds of men that he commanded in foreign lands, there never arose the slightest dissension, either among themselves or against their leader, both during his periods of good and bad luck. This could not have arisen from anything other than his inhuman cruelty, which, along with his many other virtues, made him always venerable and terrifying in the eyes of his soldiers. Without that quality, his other virtues would not have sufficed to attain the same effect. Having considered this matter very superficially, historians, on the one hand, admire these deeds of his, and on the other condemn the main cause of them. (The Prince - Niccolo Machiavelli - Oxford p.59)

Conclusion on fear
Let me conclude, then - returning to the issue of being feared and loved - that since men love at their own pleasure and fear at the pleasure of the prince, the wise prince should build his foundation upon that which is his own, not upon that which belongs to others: only he must seek to avoid being hated, as I have said. (The Prince - Niccolo Machiavelli - Oxford p.59)


Surroundings

Who should be around a good prince?
Since, then, a prince must know how to make use of the nature of the beast, he should choose from among the beasts the fox and the lion; for the lion cannot defend itself from traps, while the fox cannot protect itself from the wolves. (The Prince - Niccolo Machiavelli - Oxford p.60)

Who should frequent the prince's house?
A prince should also demonstrate that he is a lover of the virtues, by giving hospitality to virtuous men and by honoring those who excel in a particular skill. (The Prince - Niccolo Machiavelli - Oxford p.78)

How to deal with malcontent people
As soon as you have revealed your intention to one malcontent, you give him the means to make himself content, since he can have everything he desires by revealing the plot. (The Prince - Niccolo Machiavelli - Oxford p.64

Avoid the flatterers
The flatterers, of which the courts are full. Because men delight so much in their own concerns, deceiving themselves in this way, that they find it difficult to protect themselves from this pestilence; while wishing to defend oneself from it brings the danger of becoming despised. (The Prince - Niccolo Machiavelli - Oxford p.81)

How to avoid flattery?
For there is no other way to guard yourself against flattery than by making men understand that by telling you the truth they will not injure you. But when anyone can tell you the truth, you lose respect. Therefore, a prudent prince should follow the third course, electing wise men for his state and giving only them permission to speak truthfully to him, and only on such matters as he asks them about and not on other subjects. (The Prince - Niccolo Machiavelli - Oxford p.82)

How to get good advice?
Therefore, it is to be concluded that good advice, from whomever it may come, must arise from the prudence of the prince, and not the prudence of the prince from good advice. (The Prince - Niccolo Machiavelli - Oxford p.82)

On accusations and manners
A prince must be cautious in believing accusations and in acting against individuals, nor should he be afraid of his own shadow. He should proceed in such a manner, tempered by prudence and humanity, that too much trust may not render him incautious, nor too much suspicion render him insufferable. (The Prince - Niccolo Machiavelli - Oxford p.57)

On when to trust your people
Such a prince cannot rely upon what he sees during periods of calm when the citizens need his rule, because then everyone comes running, everyone makes promises, and each person is willing to die for him since death is remote. But in times of adversity, when the state needs its citizens, then few are to be found. And this experiment is all the more dangerous since it can be tried but once. Therefore, a wise prince must think of a method by which his citizens will need the state and himself at all times and in every circumstance. Then they will always be loyal to him. (The Prince - Niccolo Machiavelli - Oxford p.37)

How to keep citizens firm?
The nature of men is such that they find themselves obligated as much for the benefits they confer as for those they receive. Thus, if everything is taken into consideration, it will not be difficult for a prudent prince to keep the spirits of his citizens firm during the siege before and after this destruction, so long as he does not lack sufficient food and weapons for his defense. (The Prince - Niccolo Machiavelli - Oxford p.39)

How healthy take control?
When the nobles see that hey cannot resist the populace, they begin to support someone from among themselves, and make him a prince in order to be able to satisfy their appetites under his protection. (The Prince - Niccolo Machiavelli - Oxford p.35)


Actions

Virtue is in the present and past.
Right consists of virtue and duty. Its subdivisions (fortitude), and temperance (temperantia). The praiseworthy (laudabile) is ‘what produces an honorable remembrance, at the time of the event and afterward’. (The Prince - Niccolo Machiavelli - Oxford p.xxviii)

Where a prince should dedicate his actions to
The two most glorious aspects of the art of the state are for Machiavelli the foundation of new political orders and the redemption of peoples. The core of the Prince is precisely dedicated to these aspects of political action. (The Prince - Niccolo Machiavelli - Oxford p.xxxvii)

A prince adapts to fortune
A wise prince must follow such methods as these and never be idle in peaceful times, but he must turn them diligently to his advantage in order to be able to profit from them in times of adversity, so that when Fortune changes she will find him prepared to resist her. (The Prince - Niccolo Machiavelli - Oxford p.52)

Adapting to the winds of fortune
One must understand this: a prince, and especially a new prince, cannot observe all those things for which men are considered good, because in order to maintain the state he must often act against charity, against humanity, and against religion. And so it is necessary that he should have a mind ready to turn itself according to the way the winds of Fortune and the changing circumstances command him. And, as I said above, he should not depart from the good if it is possible to do so, but he should know how to enter into evil when forced by necessity. (The Prince - Niccolo Machiavelli - Oxford p.61)

On how the prince is judged
Men in general judge more by their eyes than their hands: everyone can see, but few can feel. Everyone sees what you seem to be, few touches upon what you are, and those few do not dare to contradict the opinion of the many who have the majesty of the state to defend them. In the actions of all men, and especially of princes, where there is no tribunal to which to appeal, one must consider the final result. (The Prince - Niccolo Machiavelli - Oxford p.62)

The consequence of an action that injures someone
Those he injures, finding themselves scattered and poor, can never be a threat to him; and all the other remain uninjured on the one hand, and because of this they should remain peaceful, and on the other hand are afraid of making a mistake, for fear that what happened to those who were dispossessed might happen to them. (The Prince - Niccolo Machiavelli - Oxford p.10)

How the prince should act in good and bad moments
A prince should live with his subjects in such a way that no unforeseen event, either bad or good, may cause him to alter his course; for when difficulties arise in adverse conditions, you do not have time to resort to cruelty, and the good that you do will help you very little, since it will be judged a forced measure, and you will earn from it no gratitude whatsoever (The Prince - Niccolo Machiavelli - Oxford p.34)

The consequences of victory 
Men are never so dishonest that they will repress an ally with such a flagrant display of ingratitude. Nor are victories ever so clear-cut that the victor can be completely free of concern, especially for justice. But if the one with whom you join loses, you can be given refuge by him, and while he is able to do so, he can help you, and you will become the comrade of a forune that may fourish again. (The Prince - Niccolo Machiavelli - Oxford p.78)


Character

On how to aim your goals
Since men almost always follow the paths trod by others and proceed in their affairs by imitation, although they are not fully able to stay on the path of others, nor to equal the virtue of those they imitate, a wise man should always enter those paths trodden by great men and imitate those who have been most excellent, so that if one’s own virtue does not match theirs, at least it will have the smell of it. He should do as those prudent archers do who, aware of the strength of their bow when the target at which they are aiming seems too distant, set their sights much higher than the designated target, not in order to reach such a height with their arrow, but instead to be able, by aiming so high, to strike their target. (The Prince - Niccolo Machiavelli - Oxford p.20)

The building of an admirable man
Nothing brings so much honor to a man newly risen up than the new laws and new institutions discovered by him. When these are well-founded and have greatness in them, they make a man revered and admirable. (The Prince - Niccolo Machiavelli - Oxford p.89)

How to avoid trouble?
By being on the spot, troubles are seen at their birth and can be quickly remedied; not being there, they are heard about after they have grown up and there is no longer any remedy. (The Prince - Niccolo Machiavelli - Oxford p.10)

How to control people?
For, besides what has been said, people are fickle by nature: it is easy to convince them of something, but difficult to hold them in that conviction. Therefore, affairs should be managed in such a way that when they no longer believe, they can be made to believe by force. (The Prince - Niccolo Machiavelli - Oxford p.22)

God doesn’t do everything, glory is in our hands
The rest you must do yourself. God does not wish to do everything, in order not to take from us our free will and part of the glory that is ours. (The Prince - Niccolo Machiavelli - Oxford p.88)

The forces on prosperity
We can observe in the affairs that lead to the end they seek- that is, towards glory and wealth- that men proceed in different ways: one man with caution, another with impetuousness; one with violence, another with astuteness; one with patience, another with its opposite. Each may achieve his goals with these different means. In the case of two cautious men, we also see that one reaches his goal while the other does not. And likewise, two men prosper equally employing two different means, one being cautious and the other impetuous. This occurs from nothing other than from the quality of the times, that either match or do not match their procedures. This follows from what I said: two men acting differently can reach the same results; and of two men acting identically, one reaches his goal and the other does not. On this also depends the variation of the good, for if a man governs himself with caution and patience, while the times and circumstances are turning in such a way that his conduct is appropriate, he will prosper. (The Prince - Niccolo Machiavelli - Oxford p.85)

How to control Fortune
Since Fortune varies and men remain obstinate in their ways, men prosper when the two are in harmony and fail to prosper when they are not in accord. I certainly believe this: that it is better to be impetuous than cautious, because Fortune is a woman, and if you want to keep her under it is necessary to beat her and force her down. It is clear that she more often allows herself to be won over by impetuous men than by those who proceed coldly. And so, like women, Fortune is always the friend of young men, for they are less cautious, more ferocious, and command her with more audacity. (The Prince - Niccolo Machiavelli - Oxford p.87)

What we have control in fortune
I consider it to be true that Fortune is the arbiter of one-half of our actions, but that she still leaves the control of the other half, or almost that, to us. (The Prince - Niccolo Machiavelli - Oxford p.84)

The three types of intelligence
There are three kinds of intelligence: one understands on its own; the second discerns what others understand, and the third neither understand by itself nor through others. The first kind is the most excellent, the second is excellent, and the third is useless. (The Prince - Niccolo Machiavelli - Oxford p.79)

How to know the nature of people?
to know the nature of the people well one must be a prince, and to know the nature of princes well one must be of the people. (The Prince - Niccolo Machiavelli - Oxford p.xxv)
For men do harm either out of fear or out of hatred. (The Prince - Niccolo Machiavelli - Oxford p.30)

How do ordinary people behave?
For ordinary people are always taken in by appearances and by the outcome of an event. And in the world there are only ordinary people; and the few have no place, while the many have a spot on which to learn. (The Prince - Niccolo Machiavelli - Oxford p.62)

People  are simple-minded
Men are so simple-minded and so controlled by their immediate needs that he who deceives will always find someone who will let himself deceived. (The Prince - Niccolo Machiavelli - Oxford p.61)

People change rulers and feel better
that men gladly change their ruler, thinking to better themselves. (The Prince - Niccolo Machiavelli - Oxford p.8)


On Leaders

Agathocles 

Good leadership
Agathocles the Sicilian, who became King of Syracuse, was not only an ordinary citizen but also of the lowest and most abject condition. A potter’s son, this man lived a wicked life at every stage of his career. Yet he joined to his wickedness such strength of mind and body, that when he entered upon a military career, he rose through the ranks to become praetor of Syracuse. Once placed in such a position, having decided to become prince and to hold with violence and without any obligations to others what had been conferred upon him by universal consent, and having informed Hamilcar the Carthaginian (who was waging war with his armies in Sicily), one morning he called together the people and the senate of Syracuse as if he were going to discuss some matters concerning the republic. At a prearranged signal he had his troops kill all the senators and the richest citizens; and when they were dead he seized and held the rule of the city without any opposition from the citizenry. Although he was twice defeated by the Carthaginians and finally besieged, not only was he able to defend his city, but, leaving part of his troops for the defence of the siege, with his other forces he attacked Africa, and in a short time he freed Syracuse from the siege and forced the Carthaginians into dire straits. They were obliged to make peace with him and to be content with dominion over Africa. leaving Sicily to Agathocles. (The Prince - Niccolo Machiavelli - Oxford p.31)

Alexander

Good leadership
Possessing great courage and high goals, he could not have conducted himself in any other manner, and his plans were frustrated solely by the brevity of alexander’s life and by his own illness. Anyone, therefore, who considers it necessary in his newly acquired principality to protect himself from his enemies, to win allies, to conquer either by force or by deceit, to make himself loved and feared by the people, to be followed and revered by his soldiers, to wipe out those who can or may do you harm, to renovate ancient institutions with new ones, to be both severe and kind, magnanimous and generous, to wipe out disloyal troops and create new ones, to maintain alliances with kings and princes in such a way that they must either gladly help you or injure you with caution- that person cannot find more recent examples than this man’s deeds. (The Prince - Niccolo Machiavelli - Oxford p.30)

Leader charchteristics
Taking all these things into account, therefore, no one should be at all surprised by the ease with which Alexander held on to the region of Asia, or by the problems others encountered in preserving the territory they acquired, such as Pyrrhus and many others. This is not caused by the greater or lesser virtue of the conqueror, but rather by the different characteristics of the conquered territories. (The Prince - Niccolo Machiavelli - Oxford p.18)

The fall of him
But let us come to ALexander. He was of such goodness that among the other laudable deed attributed to him is this: in the fourteen years he ruled the empire, he never put anyone to death without a trial. Nevertheless, since he was considered effeminate and a man who let himself be controlled by his mother, he was despised, and as a result, the army plotted against him and murdered him. (The Prince - Niccolo Machiavelli - Oxford p.65)