This paper explains the nature and origin of what I am calling Transgressive Realism, a middle path between realism and anti-realism which tries to combine their strengths while avoiding their weaknesses. Kierkegaard created the position by merging Hegel’s insistence that we must have some kind of contact with anything we can call real (thus rejecting noumena), with Kant’s belief that reality fundamentally exceeds our understanding; human reason should not be the criterion of the real. The result is the idea that (...) our most vivid encounters with reality come in experiences that shatter our categories, the way God’s commandment to kill Isaac irreconcilably clashes with the best understanding of ethics we are capable of. I explain the genesis of this idea, and then show it at work in Heidegger and Levinas’ thought. Understanding this position illuminates important aspects of the history of continental philosophy and offers a new perspective on realism. (shrink)