Quotes from book
The Prince

The Prince is a 16th-century political treatise by the Italian diplomat and political theorist Niccolò Machiavelli. From his correspondence, a version appears to have been distributed in 1513, using a Latin title, De Principatibus . However, the printed version was not published until 1532, five years after Machiavelli's death. This was carried out with the permission of the Medici pope Clement VII, but "long before then, in fact since the first appearance of The Prince in manuscript, controversy had swirled about his writings".Although The Prince was written as if it were a traditional work in the mirrors for princes style, it is generally agreed that it was especially innovative. This is partly because it was written in the vernacular Italian rather than Latin, a practice that had become increasingly popular since the publication of Dante's Divine Comedy and other works of Renaissance literature.The Prince is sometimes claimed to be one of the first works of modern philosophy, especially modern political philosophy, in which the "effectual" truth is taken to be more important than any abstract ideal. It is also notable for being in direct conflict with the dominant Catholic and scholastic doctrines of the time, particularly those concerning politics and ethics.Although it is relatively short, the treatise is the most remembered of Machiavelli's works and the one most responsible for bringing the word "Machiavellian" into usage as a pejorative. It even contributed to the modern negative connotations of the words "politics" and "politician" in western countries. In subject matter it overlaps with the much longer Discourses on Livy, which was written a few years later. In its use of near-contemporary Italians as examples of people who perpetrated criminal deeds for politics, another lesser-known work by Machiavelli which The Prince has been compared to is the Life of Castruccio Castracani.

“You don't avoid such a war, you merely postpone it, to your own disadvantage.”
Source: The Prince (1513), Ch. 3 (as translated by RM Adams)
Context: If someone puts up the argument that King Louis gave the Romagna to Pope Alexander, and the kingdom of Naples to Spain, in order to avoid a war, I would answer as I did before: that you should never let things get out of hand in order to avoid war. You don't avoid such a war, you merely postpone it, to your own disadvantage.

Variant: It must be considered that there is nothing more difficult to carry out, nor more doubtful of success, nor more dangerous to handle, than to initiate a new order of things.
Source: The Prince (1513), Ch. 6
Context: It ought to be remembered that there is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things. Because the innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new. This coolness arises partly from fear of the opponents, who have the laws on their side, and partly from the incredulity of men, who do not readily believe in new things until they have had a long experience of them.

“Never attempt to win by force what can be won by deception.”
Misattributed
Source: Quote allegedly from The Prince, but not found there textually.

Source: The Prince (1513), Ch. 15
Context: Many have imagined republics and principalities which have never been seen or known to exist in reality; for how we live is so far removed from how we ought to live, that he who abandons what is done for what ought to be done, will rather bring about his own ruin than his preservation.

“The best possible fortress is—not to be hated by the people.”
Variant: Variant translation: The best fortress which a prince can possess is the affection of his people.
Source: The Prince (1513), Ch. 20: 'Are fortresses, and many other things to which princes often resort advantageous or hurtful?'

“It is the nature of men to be bound by the benefits they confer as much as by those they receive.”
Source: The Prince (1513), Ch. 10; translated by W. K. Marriot