Taking the Kantian interest in mental illnesses in Anthropology from a Pragmatic point of view as a starting point, the following will focus on some aspects concerning cognitive disorders from a gnoseological perspective and some observations of practical and moral philosophy. After a terminological examination of the concept of pathology [Pathologie] and disease [Krankheit], I will analyze the relationship between 1. mental illness and cognitive faculty and the impact that cognitive disorders have on the formation of representations which can motivate practical action; 2. public sphere and private sphere as regards illness and normality. Secondly, I will investigate if and how it is possible to speak about “autonomy” in the case of mental disorder or if, for Kant, the mentally ill patient is only defined by the necessity of natural laws. In addition to this theoretical question, the third part of the paper will focus on the problem of the judgment of imputation in fragile subjects and psychopaths, explaining the Kantian position of legal protection. In the last paragraph, however, I will provide a positive interpretation of the illnesses of the faculty of desire, i.e. the Kantian conception of passions in politics.