Concentrating on G.W.F. Hegel’s controversial Naturphilosophie (1830), Part I ventures the following thesis: Hegelian nature is characterized by a “constitutive lack.” Insofar as the natural register lacks the precision and necessity immanent within the dialectical developments of conceptual thought it is capable of radical novelty—the unexpected. This is important: it offers a sense of how the natural register is open to thought and yet, simultaneously, a source of that which has the perpetual possibility of undermining conceptual distinctions and anticipations. The remainder of the project systematically maps what such a conception of nature must mean in terms of Hegel’s concept of spirit (Geist). Consequently, Part II analyzes Hegel’s bizarre account of psychopathology. The central thesis in this context claims that what Hegel’s speculative analysis of ‘madness’ shows us are the ways in which subjectivity might be dominated by its material-instinctual dimension as it unfolds within the unconscious depths of concrete subjectivity. Subjectivity retains the perpetual possibility of regression insofar as it reverts to being materially (maternally) determined strictly by way of externality. Questioning the presupposition of nature’s complete sublation, Part III focuses on Hegel’s political writings. Hegel’s analysis of criminality and punishment allows for the possibility of what we will call “surplus repressive punishment.” A surplus repressive punishment, a brute form of natural external pressure, would constitute spirit’s, i.e. freedom’s, “regressive de-actualization” at both the individual (subjective) and intersubjective (objective, communal) levels. Therefore, surplus repressive punishment, as an expression of spirit’s naturality, serves to undermine spirit’s objective actualization in its entirety. The problem of nature remains very much an active dimension of spirit’s concrete actualization at the socio-political level. The project offers a precise indication of how Hegel’s philosophy of spirit, i.e. his philosophy of freedom, is one intertwined with the problem instantiated by the matrices of nature. Sensitivity to this problem, that there is a problem here, and that Hegel’s system can be pursued to address it is one of the not always recognized merits of his thought. Simultaneously, Hegel’s system becomes surprisingly relevant for our contemporary world insofar as nature remains a problem for our living present.