Chapter 16 threats the subject of liberality (and as mentioned at the end of the last post, justice).
Beginning, then, with the first of the above-mentioned qualities, I say that it would be good to be held liberal; nonetheless, liberality, when used so that you may be held liberal, hurts you. For if it is used virtuously and as it should be used, it may not be recognized, and you will not escape the infamy of its contrary. And so, if one wants to maintain a name for liberality among men, it is necessary not to leave out any kind of lavish display, so that a prince who has done this will always consume all his resources in such deeds. In the end it will be necessary, if he wants to maintain a name for liberality, to burden the people extraordinarily, to be rigorous with taxes, and to do all those things that can be done to get money. This will begin to make him hated by his subjects, and little esteemed by anyone as he becomes poor; so having offended the many and rewarded the few with this liberality of his, he feels every least hardship and runs into risk at every slight danger. When he recognizes this, and wants to draw back from it, he immediately incurs the infamy of meanness.
Machiavelli is emphasizing that there is no point being liberal (just) without it being noticed.
There is a clear recognition of the fact that if one gives and gives and gives, then one will become poor and thus will have to rob one’s citizens to keep on giving.
Think here of healthcare (Medicare and Medicaid) and pensions (Social Security). Eventually the money of today proves insufficient, or rather, those alive today do not really want to pay what is necessary. The answer, then, is to rob future generations who have no representatives and yet who are taxed through borrowing. But this too is not sustainable indefinitely. One day the Ponzi scheme will come crashing down, but those who benefitted will not likely suffer any consequences.
To be liberal one is liberal with few and rapacious with many. It is preferable to be mean with few and liberal with many, but this entails redefining what it means to be liberal: instead of giving much it must become taking little.
Is there another option, conquest perhaps? What if the Iraq “War for Oil” really had been for the oil?