"The Prince" by Machiavelli

Quite enjoyed this book; very short and to the point.  It was written by Machiavelli in order to aid and garner favor with Lorenzo de' Medici, whom Machiavelli saw as the best person to bring prosperity and order to Italy.

TL;DR - a prince must have an outer appearance of virtuousness (mostly for the purpose of endearing himself to the common people) while maintaining both a capacity for force and craftiness in order to effectively carry out his agenda with the end of safeguarding his state from outside forces.  He must not rely on outside assistance unless there's no other option since even in victory he would be beholden to another.  Fear is better than love since love wilts in the face of danger while fear of punishment keeps others loyal while facing danger.  Frugality is better than charity.  Power is better than virtue.

There's much more, but you can check out my summary of each chapter below if you wish.

I've heard mostly negative things about this book over the years, but now that I've finally read it I can see the pragmatic commonsense nature of the work.  Though I would be remiss to say that this is a faultless guide for how to rule.  It's focus on "pragmatism" over virtuousness is troublesome and reeks of a desperate man who saw no alternative.  Also, the book makes it clear at the beginning that this is purely for the edification of princes ruling over principalities.  He avoids the subject of the rule of republics since it is expounded upon in another of Machiavelli's work.  Even if it was the best guide ever, some might find it difficult to adapt everything to modern governments which are much larger and more complex than the principalities of the day that are spoken of in the book.

After reading it, I am on the side that sees this as the work of a patriot who was desperate to have his country unified and strengthened by the rule of one whom he saw as a savior figure, that being Lorenzo de' Medici.  I highly recommend giving it a read.  You will certainly find yourself thinking a lot about modern politics with reference to Machiavelli's insights.

Thanks for your time and attention.

For those who are interested, below are my summaries/notes on each chapter.  Apologies in advance for their unrefined nature.

1. There are principalities and republics.  Of principalities there are inherited and created (this includes those that a prince acquires by force from another)
2. Inherited principalities are easier to maintain since the people are used to the family in power ruling.  Don’t change the laws to much and don’t give great harm to the people and they’ll be content with how things are.
3. Because of the preceding it’s much more difficult to maintain a new principality.  The people are likely to throw you over for another in the hopes that things can be better.  And you can’t trust those who helped you to overthrow the previous authority.  It’s easiest when laws and language are the same.
4. A prince should ideally take up residence in the principality so that he can more closely observe dissidence and nip it in the bud.  He should make examples of dissidents to quelch future rebellions as much as possible.  An easier method is to set up colonies with those loyal to him so that the previous population is scattered and weakened against rising up against the prince.
5. When having conquered a place that once lived by its own laws it can be advantageous to allow them to continue under the old laws while taxing them and establishing a loyal oligarchy.  The oligarchy will secure loyalty for the prince if only for the sake of keeping the power that the prince has bestowed upon them.  The most effective is to decimate the place. Older traditions and laws will remain in memory otherwise which will always threaten to have the people rise up against a conqueror.  Though places that have been ruled by princes before will tend to submit to a new ruler once the old family has been taken out since the people don’t know how to exist without a ruler.
6. Princes will tend to demand more respect and loyalty by taking a principality by force.  Prowess in battle doesn’t rely on lukewarm support from those who think they may be able to benefit from his eventual take over.  Prowess commands respect and admiration even of the conquered.
7. Princes will tend to demand more respect and loyalty by taking a principality by force.  Prowess in battle doesn’t rely on lukewarm support from those who think they may be able to benefit from his eventual take over.  Prowess commands respect and admiration even of the conquered.
8. If a prince is to gain a principality through cruelty and backstabbing he should get it all done at once so that the memory and resentments can die in the people lest they prove troublesome and unwilling to bear any future atrocities if he must continue in cruelty to maintain rule.
9. Nobles and common people are naturally opposed to each other.  Either will seek to bring a prince to power to represent their interests.  In both cases the prince is to seek the friendship of the common since the nobles are greedy and always ready to oppose the prince if he doesn’t do as they desire.  The nobles consider themselves the prince’s equal.  The people will not.  The prince stands alone at the top to the common.  Having the people on his side will protect him against the nobles lest the common people rise against the nobles for taking the prince they appreciated.
10. A prince should fortify defenses as much as his means of aggression.  If the city is besieged by an aggressor then the prince can take the opportunity to unite and impassion the people to take up the defense.  If they win, then the prince has ennobled himself to the people all the more.
11. Ecclesiastical principalities unique.  There are sustained  by powers that cannot be fathomed by humans.  And a prince never truly rules one of these.  They are ruled by religious principles rather than human authority.  But the Church has in the past expanded its power through arms.
12. A good state has a good army and good laws.  A prince may rely on his own men, mercenaries, or auxiliary armies.  It’s best to rely on his own men.  Mercenaries have bad morale and are disloyal except to money and the leader’s own ambition.
13. Auxiliary units are borrowed from a more powerful ally.  These are just a terrible as mercenaries.  Either they lose leaving the prince defenseless or they win leaving the prince indebted to whom the troops were borrowed. A prince must command his own troops to secure his principality.
14. A prince’s main concern should be the art of war.  The armed (his troops) won’t have respect for the unarmed prince.
15. A prince should not concern himself with the virtuous life since it is impossible to live as such, but rather should dedicate himself to the practical attainment of safeguarding his state even through what would be considered non-virtuous means.
16. Liberality (i.e. free spending and generosity) endears people to a prince at first, until the money runs out and the prince must resort to taxation to keep up his liberality, which will only breed contempt.  Parsimony (i.e. frugality and unwillingness to spend money) may breed contempt at first, but will bear the fruit of generosity in the future.  Parsimony allows the prince to store up for such times as he will need those resources.
17. A prince should be prudent when dealing out compassion.  Too much and even disloyal traitors will not be adequately made an example of and will sow discord amongst the prince’s subjects.  And it is more practical to be feared than loved.  Humans are fickle and ungrateful.  When hard times occur love can dissipate far more efficiently than fear will.  Fear of punishment for the desertion of loyalty is a more effective motivator. But the prince must take care to not sow hatred amongst the fear.
18. A prince must emulate the fox and lion.  The fox is crafty and deceitful whilst the lion is strong and has force.  A prince must be able to be crafty and hide his true motives to manipulate others to his advantage while also retaining the necessary force to do what needs be done.  Have a surface level impression of virtuousness to the people will aid the prince. As long as the prince appears virtuous and delivers the results that the people want, his state is secured.
19. A prince should never be held in contempt and hated.  He can avoid this mostly by not taking his people’s property and women and not injuring their honor.  Having neither the hate nor scorn of his people is a strong defense against internal conspiracies to overthrow him.  The conspirators will now have to consider the consequences of overthrowing the prince that is loved by his people.  It’s impossible to avoid all hatred so a prince should seek to appease the most important groups of the people; the troops being the most important.  But the troops should never be appeased to the detriment of the common people.
20. In essence, a prince should have the love of the people in order to stave off the possibility of rebellion by conspirators since the people are more powerful than the armies on average.  But there have been occasions in which it was prudent for a prince to be more amenable to the rapacity and violent nature of the soldiers.
21. It’s good for a prince to arm those who have none who can help me take over a principality for this creates trust.  Disarming breeds distrust. He should be wary of those who are discontented with their government and help him to take over for they can just as easily become discontented with him.  He should prefer those who are his enemies when he takes over.
22. A good prince is never neutral; he will be irresolute and a coward in the eyes of people and allies.  And must never, unless absolutely necessary, appeal to a stronger ally for aid for then he will be more inexorably beholden to the stronger ally if victory is achieved.
23. When choosing a servant a prince should never choose one that has personal concerns outside the prince.  The servant should be fully focused on matter pertaining to the prince.  And the prince will retain the servant’s loyalty by showing appreciation and honouring him enough to let him know what he gets by the prince’s kindness.
24. A prince should let it be known that others should only ever speak the truth to him and only ever when the prince asks.  Good counsel comes of a wise prince who has prudence.  Otherwise the prince is split on counsel with each counselor attempting to benefit his own position.
25. In times of peace a slothful prince will neglect prudence thinking that there can’t be change that will upend his rule.  A conquering prince that establishes a new principles with new laws and arms the populace is doubly good.  A prince is doubly shamed who inherited and lost it through lack of prudence and slothfulness.
26. A prince should always be read to change to meet fortune while not bowing to caution.  Fortune is a woman, and thus is only properly subdued by a violent and young man who can better command her.
27. Final chapter in which Machiavelli appeals to Lorenzo de Medici to take the preceding advice, with the addition of some battle strategy against enemies, in order to bring Italy to the glory it deserves under a ruler that can get the job done.