The first hate speech law in Japan contains no legal sanctions. However, it has a de facto impact on society. In fact, drawing on the hate speech law, a local court ordered an injunction against repeated hate speech. However, such a decision have some problems. A particularly important, theoretical problem is that prior injunction based on repeated speech is prior restraint in the first place. Moreover, this problem can be paraphrased with the following question: the constitutionality of restricting future speech based on negative estimation of past speech. So, drawing on Clay Calvert’s discussion about the constitutionality of performance bonds, this Note aims to consider the constitutionality of regulation of the future speech of “past bad speakers”. In this discussion, Calvert argues that such regulative measures blur the distinction between prior restraint and subsequent punishment, and that such measures “are inherently content-based measures and thus should always be subject to strict scrutiny”. Then, by considering this argument, this Note proposes some questions to the arguments of Japanese free speech academics.