The Cognitive Behavioral Therapy intervention of cognitive restructuring leads to mood stabilization by identifying, challenging, actively disputing, and ultimately replacing maladaptive and irrational thoughts and behaviors. The case study of an adult child of Holocaust survivors explores the limitations of success with cognitive restructuring. In this case, transgenerational transmission of trauma as a second generation Holocaust survivor was the first of several subsequent first-hand experienced traumas. These additional traumas, as well as the primary coping mechanism of overeating leading to diet-resistant morbid obesity, are explored through the lens of the Holocaust. It is suggested that the layering of multiple traumatic events deeply ingrains cognitions and life philosophies, thereby creating resistance to permanent cognitive restructuring. Therapists must determine the specific layer of trauma that is associated with maladaptive cognitions and recognize that automatic thoughts which may be adaptive and appropriate in response to a specific layer of trauma may be dysfunctional outside of that trauma.