The phenomenon of the aesthetics of pure negativity arose as a result of the loss or deliberate ignoring by humans of the postmodern objective basis and the defining contradictions of the historical process. “Desertion from history” (Ortega y Gasset), through the artificial formation of a time-space of subjectivity, provoked a particular situation of regressive phenomenological semantics with equally regressive aesthetics. The narrowing of life’s meanings as “diminishment of man” (C. Noica) led to the degradation of the subject of history and the limitation of his existential aspirations by societal functionality for the sake of vitality per se. “Non-correspondence to one’s own concept” (Hegel) among all social strata in the context of their place and significance in the historical process, the regression of historical reason, and the degradation of humanity’s theoretical self-awareness generated the effect of shagreen skin of subjectivity. This last is accompanied by a mismatch of simplified thinking to the highly complex contradictions of objective reality, simulations of subjective realities acting as fragmentary abstractions, artificial stagnations of mediations granted autonomous status, and the impossibility of realizing subjective desires in a disintegrating world. Ultimately, it results in essential non-realizability. This deregulation of subjectivity is “rooted” in the deregulation of both its internal and external forms and its no less deregulated relationship with the equally deregulated historical reality. This reversed system of deregulated subsystems is accompanied not only by the chaos of mismatches between subjectivities and objective reality—due to irrationality and absurdity, it moves towards semantic emptiness and real exhaustion. This highlights the necessity to return to understanding the law of the fundamental basis of history and the reproduction of its essential contradiction in the mode of resolving the universal-historical contradictions of the present.