To take satisfaction in outwitting someone who themselves is a deceiver suggests a moral complexity that transcends simple notions of right and wrong. Machiavelli’s idea encapsulates the thrill not just of successful deception, but of deploying cunning against those who operate by the same rules. When a person deceives an honest soul, there is often guilt or at least recognition of a moral trespass; but when the deceiver becomes the victim, the scales seem somehow balanced, making the outcome more pleasurable. It is not simply the act of deception, but a restoration of equilibrium and an assertion of intellectual superiority over one who themselves values cunning and manipulation.
This sentiment appeals to the competitive instincts in human nature. There is an added delight in besting someone at their own game. The one who deceives for gain or amusement often operates under the assumption of their own cleverness, sometimes with contempt for the simpler, more trusting people around them. When such a person becomes the target, their exposure delivers not just revenge but satisfaction in disrupting a hierarchy where they claimed a higher moral or intellectual ground. Outwitting the deceiver validates both the strategy used and the intellect of the one who engineers the reversal of roles. The pleasure is thus doubled: first by success in deception, and second by achieving victory over a peer in cunning, a person less likely to fall prey and more deserving, by their own conduct, of such poetic justice.
Underlying this idea is a recognition that manipulation is rarely one-sided. Human interactions are often fraught with hidden motives and shifting allegiances. Outsmarting someone who specializes in subterfuge becomes both a warning and a lesson: trust, but be vigilant; admire ingenuity, but be wary of its abuse. Ultimately, turning the tables on a deceiver offers both personal satisfaction and a meaningful commentary on the nature of power and humility.
