The covid-19 pandemic and the increasingly polarized political situation in many countries today have highlighted the significance of various humanly natural intellectual mistakes, cognitive biases, and widespread inferential errors. This essay examines, at a philosophical meta-level, the relation between our natural epistemic errors and the kind of humanly unavoidable transcendental illusion analyzed by Immanuel Kant in the Transcendental Dialectic of the First Critique. While both kinds of illusion are usually primarily discussed in an epistemological context, my approach is not exclusively (...) epistemic. Rather, my main argument extends the broadly Kantian critique of reason – as a critical via negativa focusing on what is epistemically “wrong” about us, as the kind of cognitive agents we human beings naturally are – into a pragmatically enriched investigation of “the negative” as constitutive of the human condition, that is, our lack of sufficiently critical epistemic and ethical capacities, including our propensity to both cognitive error and moral evil. Our being inescapably inclined to manifest such negativities in our epistemic and ethical lives, and our insufficient awareness of doing so, are, arguably, “transcendental facts” about us, to be critically examined in terms of a Kantian-cum-pragmatist philosophical anthropology. This significantly enriches our picture of transcendental philosophy. (shrink)