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In this commentary on Jill Gentile’s essay “On Having No Thoughts: Freedom and Feminine Space,” Ann Pellegrini, PhD, asks how sociopolitical variables simultaneously constrain and constitute the “free” in “free association.” Posing this question historically, Pellegrini goes back to the founding moments of psychoanalysis to explore how Freud’s own complicated position as a Jewish man in one of the most anti-Semitic countries in Europe affected what it was possible to say, hear, and see in the analytic encounter.