Abstract.The author questions himself about what is known as “the paradox of blackmail,” that is, the fact that blackmail is the result of the combination of two ways of behaving which are often both lawful if taken individually, but unlawful once they are connected. The author also examines whether the harm principle typical of liberal orders provides the justification (the rationale) for the assumption of blackmail as a crime, or whether it is instead necessary to turn to another justificatory basis: the exploitation principle. However, as this principle leads to legal moralism, it opposes a liberal ethics. Thus, one is faced with the dilemma of either accepting the harm principle thus decriminalizing blackmail, or accepting the exploitation principle and going against principles of liberalism. To escape this dilemma the author distinguishes between various types (five categories) of blackmail, concluding that only non‐paradoxical types fit the common‐sense expectation of criminal