Pseudo-Dionysius the Areopagite should be celebrated as the Doctor of Darkness (Doctor Tenebrarum). In a Gothic style that reflects the depth of his many masks, his enduring achievement has been to have conceived of a theological grammar to speak of God beyond the haunting spectre of both ancient and modern nihilism. His Christian theological grammar is distinguished by speaking in the sense of a hyperbola (ὑπερβολή) or excess of signification, which signifies beyond yet within the world: first in the positive or cataphatic grammar, a positive judgment speaks of God; second in the negative or apophatic grammar, a higher or hyper-negative judgment annuls the positive, even as it speaks of God ‘beyond being’, and ‘beyond intellect’, as the absolutely originary source of any such positive judgment; and, third in the proportionate or analogical grammar, this procession of divine Power reciprocally annuls the infinite repetition of all such negative judgments, even as, from the centre of this cycle, it constitutes the absolutely higher ground from which alone speech of God is warranted. At the centre of this cycle, Christ can be acknowledged by faith to descend into the depths of the negative so as to shine from within the essentially proportioned and hyperbolic grammar of analogy. The elements of the Latin Scholastic analogy of being can, as this commentary will show, be reconstructed from Pseudo-Dionysius’s hyperbolic grammar. In these hyperbolic arcs, the infinite repetition of hyper-negative judgments is annulled, and yet, in a reciprocal determination, equally constituted to virtually proceed from a higher ground in the essential proportions of analogy. Like fireflies that carry the torch of the Sun before the doors of night, the theological grammar of Pseudo-Dionysius the Areopagite can be shown to be radically shaped by a Christian and Trinitarian theology, in which Christ the Logos is the originary ground and source, not only of the hyper-negative, but of the essential proportions of the analogia entis.