Machiavelli in general believes generosity is a trait that a prince should not exercise honestly unless something can be gained from it, “liberality exercised in a way which does not bring you the reputation for it, injures you”(Chapter 16). Machiavelli then goes on to argue that a prince who is very generous in improving the lives of the people overall will eventually need to increase taxes to afford these amenities. This will cause the people to begin to hate you says Machiavelli as they generally ignore what is being done for them.
However, according to Machiavelli there are some situations in which being generous can be advantageous,” seeing that with his economy his revenues are enough, that he can defend himself against all attacks, and is able to engage in enterprises without burdening his people; thus it comes to pass that he exercises liberality towards all from whom he does not take…” (Machiavelli ch.16) In this he is saying that a prince should bide his time and accumulate wealth and once there is a healthy surplus of wealth the Prince can then use this to appear generous to his subjects however the Prince should be wary not to overspend.
In a nutshell Machiavelli is saying that Generosity can be very useful as long as when a Prince is generous he makes sure to spread the word and to create an advantage out of it and the Prince should only be generous when he can afford it and when it is plausible to do so.
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