As correctly noticed by Vincent Colapietro, one of the few authors who have approached the topic, pragmatism and psychoanalysis followed parallel paths. The most obvious comparison between James and Freud did not seem to cast new light neither on the understanding of psyche nor on the two movements of thought. However, a different and less obvious comparison between Peirce and Jung might be more fruitful, notwithstanding the progressive antipsychologism of Peirce’s approach to logic. As we are going to see, this unusual comparison is due to the strong epistemic and philosophical import of Jung’s mature theories as well as to Peirce’s tendency to provide a general theory of the mind, both conscious and unconscious. Therefore, this paper will try to understand the attitude that Peirce had towards psychology (I), to recall the part of Jung’s theory that has to do with Peirce’s pragmatism (II), to assess the relationship between the two authors and the reciprocal advantage in mutually integrating their theories (III).