This paper examines the construct of countertransference and its role in the treatment of a traumatized child, with emphasis on the perspective of a psychology trainee. A review of the countertransference literature is provided and then multiple aspects of the phenomenon are explored within the context of psychotherapy with one 11-year-old boy who was a victim of trauma. The relevance of three specific countertransference roles—rescuer, abuser, and victim—is depicted through an in-depth account of psychotherapy sessions with the child. The paper emphasizes the underlying challenges associated with taking on these three countertransference roles as a nascent and curious trainee.