The article is devoted to the study of the problem of the doctrinal identification of freedom and inequality by classical liberalism and neoliberalism. Identifying the features of the naturalistic and theological approaches to the manifestation of inequality in human communities, the author notes the philosophical justification of the legal argumentation of inequality in the theories of natural law and the social contract of modern thinkers. The appeal to the value dynamics reflected in the slogans of the French revolution of the 18th century allows the author to reveal the gradual displacement of the priorities of “Equality” and “Brotherhood”, which were put forward by the revolutionary democracy, by the liberal movements. The final statement of Locke’s version of the orientation of classical liberalism on the triad “Freedom. Property. Life”, according to the author, logically determines the identification of freedom with inequality, and equality with slavery by representatives of liberal circles. The development of the concepts of “social solidarity” by the theorists of neoliberalism, according to the author’s proof, does not change the liberal attitude to “freedom in inequality”. The analysis of the categories of freedom and inequality allows the author to formulate the contradictions of this provision. The article concludes that with the aggravation of the derived contradiction to the maximum, the risk of self-denial of liberalism increases.