Despite an early interest, Freud explicitly rejected philosophy, because of its “speculative” character. He struggled with balancing the intellectual appeal of philosophy with the certainty he hoped to find in positivist science. Putting aside the scientific status of Freud's work, the author re-examines Freud's attitude towards philosophy. Failing to recognize the assumptions of his investigations, Freud segregated psychoanalysis from philosophy on the charge that philosophers equated mind with consciousness, putatively propounded unfounded speculations, and assumed false conclusions about comprehensiveness. However, Freud never completely abandoned his initial philosophical proclivities. His own contributions to cultural history, social philosophy, notions of personal identity, and the humanistic thrust of psychoanalysis, demonstrate that he continued to address his earliest interests in philosophical questions. The author elucidates the philosophical complexity of psychoanalysis and concludes that a reconsideration of Freud's self-appraisal of his intellectual commitments is warranted.