Question

Read this paragraph from chapter 5 of The Prince.

Whenever those states which have been acquired as stated have been accustomed to live under their own laws and in freedom, there are three courses for those who wish to hold them: the first is to ruin them, the next is to reside there in person, the third is to permit them to live under their own laws, drawing a tribute, and establishing within it an oligarchy which will keep it friendly to you. Because such a government, being created by the prince, knows that it cannot stand without his friendship and interest, and does its utmost to support him; and therefore he who would keep a city accustomed to freedom will hold it more easily by the means of its own citizens than in any other way.

What is the most important idea the author wants readers to know?

There are three means of holding a newly acquired state that is accustomed to freedom.
The easiest way to hold a newly acquired state is to play on the citizens’ own interests.
A government created by a prince knows that it is in its own interest to remain loyal to the prince.
One way to hold a newly acquired state accustomed to freedom is to establish a friendly government.

Answer 1

"The easiest way to hold a newly acquired state is to play on the citizens’ own interests." — because Machiavelli argues that creating a friendly government of locals (an oligarchy) who depend on the prince makes holding the city easier than occupying or destroying it.