This paper addresses a treatment relationship that tests the analyst's capacity for empathy within an impinging political context. It involves a Ferenczian “relaxation of technique” within the analytic frame, while the analytic couple attempts to negotiate a polarized transference and countertransference. Specifically, within a long-term treatment imbued with positive transference, my patient becomes openly outraged by my insensitive anti-Trump remarks. Increasing confrontations around the expression of political views illuminate our otherness. He complains of psychic ostracism within a liberal cultural context, which tolerates no divergence from mainstream liberal ideas or discourse. I come to embody the oppressive other: the liberal “thought police”, “silencing” him for his perspective. Empathic breaches between us take center stage: how I don't see the world as he does, and don't see or hear him.