The political is understood as an essential, irreducible aspect of our self-representations and an undeniably consequential factor in our difficulties in living. It can thus no longer be considered taboo in psychoanalytic theory and practice. I examine challenges of working with political material, especially as treatment conducted during the highly partisan, embattled Trump Era may instantiate fierce complementarity or collusive concordance in the dyad. I argue that we can neither ameliorate patients’ suffering nor widen and deepen understanding of their lives if we don’t help them discover how their (and our) embeddedness in particular historical and sociopolitical webs of competing interests hold them (and us) in place. Psychoanalysis’s disavowal of sociopolitical impacts is historicized, and its gradual theoretical relegitimization is traced. The relational turn’s emphasis on the analyst’s subjectivity, intersubjectivity, coconstruction, mutual recognition, and advances in cognizing social inequities offer theoretical scaffolding and strategies of engagement.