This paper proposes a retro-modernist interpretation of Pollock’s painting “Number 5” (1948). The paper rejects the view that abstraction forms a simple dichotomy with figurative representation; instead, abstraction is seen as an inherently ambiguous quality, inviting contradictory interpretations that form an antinomy of abstraction. Here, the paper employs the notion “antinomy” in a sense loosely based on Kant’s theory of transcendental illusions in the Critique of Pure Reason. The antinomy concerns sensibility. The thesis maintains that the canvas presents raw sensory intuitions without or prior to their discursive mediation in terms of concepts, principles, or categories. The painting, on this view, explores the forms of sensibility, in particular the non-representational significance of undetermined flat surfaces. The anti-thesis states that raw sensuous intuitions are always already prefigured by multiple layers of effective history. Accordingly, the painting signifies through its implicit dialogue with the inherited tradition. This antinomy of abstraction cannot be resolved or integrated into a higher synthesis; yet, it provides a hermeneutic grid for a retro-modernist interpretation of Pollock’s “Number 5.”