If I had to argue against Machiavelli’s famous adage, I would say that he does not understand what love really is. In the passage where he says that it is better to be feared than loved (if you can’t have both), he uses a definition of love that is closer to self-interest than to what I would think of as real love.
To really understand what Machiavelli is saying, we need to look at his actual words. He says that “as long as you succeed they (your people) are yours entirely” but that they will quickly turn against you when you actually need them to do something for you. A little later on, he says that “love is preserved by the link of obligation” and that people will break that link when it is to their advantage. In both of these cases, I would say, he uses a definition of love that is not the one we would use today.
I would argue that love is not based on a person’s success. If we really love someone (at least if we are talking about political leaders) we love them for their ideas and their character. These are not things that succeed or fail. We trust them as people and are therefore willing to follow them.
I would argue that love is not based on obligation. We do not love political leaders because they give us things. Instead, we love them because they stand for things that we believe in. We love them if they seem to be passionate about the same things we are passionate about. In other words love is not based on “the link of obligation” but on shared beliefs and values.
If we understand love in the right way, then (the argument goes) we can see where it is better to be loved than feared. If people follow leaders out of fear, they will break away from the leader as soon as the leader is too weak to inspire that fear. They will always be looking for an escape and the leader’s rule will be tenuous (just think of how quickly the Soviet Union collapsed when people no longer feared that government). By contrast, if people follow their leaders because they trust those leaders and feel that the leaders care about the same things they (the people) care about, the bonds will be much stronger. People will not be looking to overthrow their leaders at the first opportunity. In this way, we can argue against Machiavelli and claim that it is better to be loved than feared.