The Prince Chapter 21
What a prince must do to be esteemed
A prince earns esteem by undertaking great enterprises. King Ferdinand of Spain is cited again as an example of a lowly monarch who gained esteem by showing his ability through great feats. In the name of religion, he conquered many territories and kept his subjects awed and occupied so that they had no chance to rebel.
When confronted with a decision to take sides among two conflicting parties, it is always better to be fully devoted to one side than to be neutral. If your allies win, you benefit whether or not you have more power than they have. If you are more powerful, then your allies are under your command; if your allies are stronger, they will always feel a certain obligation to you for your help. If your side loses, you still have an ally in the loser. It is wise for a prince not to align with a stronger force unless compelled to do so. The most important virtue is having the wisdom to know what is the least risky venture and then pursuing it courageously.