As a candidate and analyst, Betsy Cohen had to face issues of Jung’s anti-Semitism. Paradoxically, Jung’s acknowledgment of a mystery in human life had supported her discovery of a more meaningful and vibrant relationship to Judaism—one that she had not found during many years of participation in a Freudian context. How could she reconcile her Jewish identity and Jung’s anti-Semitism? As it is not possible to confront Jung directly, she imagines that her grandmother and namesake, a contemporary of Jung, was able to do this. Using the device of an imaginary correspondence, Dr. Cohen constructs a letter her grandmother might have written, as well as Jung’s response to that letter. In imagination, both the author’s grandmother and Jung have the courage to confront and give voice to being wounded and to having wounded. Specific instances of Jung’s anti-Semitism are brought out and then acknowledged. Silence from fear would have resulted in a rupture between them as individuals—and, by proxy, a rupture between Jews and the aspects of Jung’s work that are of profound value. Having imagined that Jung could, in retrospect, acknowledge his errors of fact and attitude, the author comes to a new stance in relation to Jung and his prejudices toward the Jewish religion and toward Jews. Drawing on Biblical text, cowardly silence is differentiated from silence in the presence of mystery. Contemplating the wisdom revealed in the text, the author arrives at a compassionate yet realistic relationship to Jung’s anti-Semitism.