The destructive influence of bullying, defined as a form of aggressive behavior involving emotional, verbal, or physical abuse, is felt in every relational configuration imaginable from dyads to large social and political groups. This article attempts to show how certain forms of bullying originate in intergenerational traumas. Using a relational systems approach to trauma and further developing my concept of “traumatic attachments,” I examine experiences of bullying in my own life. I attempt to show how Freud’s life and thought reflect themes of bullying as a response to the traumatizing anti-Semitism that infiltrated his development; and I briefly describe my work with a patient whose experiences of being the victim of bullying may be traced back to her grandparents’ generation. I reflect on how intergenerational traumas in my life may have sensitized me to being perceived as a bully by her.