South Africa cannot ignore the far-reaching influence of its colonial and apartheid history on the psychological functioning of its people. Psychotherapy as a fundamental psychological intervention approach cannot ignore its evolving history as the architect of the social psyche and of an individual’s psychological functioning. With regards to psychodynamic psychotherapy, the literature has lamented this therapeutic approach’s lack of consideration of the impact of the colonial and apartheid historical trauma on the prevailing sociocultural and mental health challenges. The crux of this article is to address this epistemological lacuna, by arguing for the integration of psychodynamic theory with cultural-historical activity theory (CHAT) for application in therapeutic processes. The article further posits that this integration needs to be introduced in training programmes for student psychotherapists who, as in the case of South Africa, are themselves the descendants of the generation that was exposed to historical trauma of colonialism and apartheid and are living with latent transgenerational trauma. To create a suitable foundation for the integration of psychodynamic theory and CHAT in psychotherapeutic practice, there is a need to apply critical pedagogical strategies in the training programmes of psychotherapists. Thus, this article further highlights the possibilities of employing critical pedagogical principles that incorporate ontological reflection, pedagogic discomfort, troubled knowledges, mutual vulnerability, strategic empathy, and compassion.