The article examines the paradoxical nature of G.W.F. Hegel’s biography and philosophical ideology. The essence of paradoxicality is substantiated by several factors – biographical, historical-philosophical, hermeneutical, and concrete-historical. The purpose of the work is to identify insufficiently known aspects of the personality and philosophical ideology of the thinker. Methodologically, the study is constructed using dialectical and historical-logical methods. The results of the study are to reveal the voluminous inconsistency of Hegel’s biography and thought; to clarify both the positive and negative aspects of his philosophical ideology. The author shows a number of paradoxes of Hegel’s philosophy: first, the understanding of development as a ‘hard’ war against itself and inattention to the multifactorial and non-linear nature of many processes; secondly, focusing on a logical idea belittles or denies the value of everything else, including living and human beings; thirdly, the desire to raise a person to ‘the highest’ position and at the same time enslave him as a universal creature and a state citizen; fourth, Hegel’s essentialism is frankly anti-existential and merciless to everything private and subjective; fifth, Hegel’s seemingly flawless scientific system suffers from inattention to the complexity and unpredictability of reality; sixth, the Lutheran religiosity of the philosopher turns out to be almost anti-Christian – with the non-recognition of the Most Holy Trinity, without the desire to become a ‘servant’ of another, etc.; seventh, Hegel’s decency and philistine ‘kindness’ are radically different from his pejorative attitude towards the female sex, other peoples, races, and civilizations. Colonialism is justified. Hence, it was quite natural for the German Nazis to turn to Hegel’s ideas. Eighth, the great dialectic has too much belittled the reality of static things, unambiguity and invariance. The novelty of the research lies in the recognition of the true causes and tasks of the thinker’s life and work; in the explanation of his main values, including his understanding of Christianity; in the clarification of the Hegel-German and Hegel-citizen positions. The conclusions of the study are related to the antithetical comparison of the ideology and philosophy of Hegel and Hesse, Hegel and Shestov. The author highlights anti-existential and racial-nationalist motives of the philosopher’s work.