Within the liberal tradition, the principle of equality of opportunity stands among the most deeply rooted. Emerging in the wake of the French Revolution, it marked the shift from the ascriptive logic that dominated ancient régime societies to the acquisitive logic of the market based on merit and individual abilities. As an egalitarian model, it confines its application exclusively to the realm of ex-ante conditions, thereby accepting inequality in ex-post outcomes and endorsing the market as a mechanism of social regulation. However, the universality of this principle is merely apparent. It represents one of the most contentious antinomies within liberal thought. The case discussed here is undoubtedly among the most significant. In numerous writings, particularly his 1901 essay, Maffeo Pantaleoni explicitly addressed the interplay between “equality of opportunity”, “initial conditions”, and the inherited wealth of economic agents, engaging in a discourse that intertwines ethical, political, and theoretical dimensions. This paper elucidates why Pantaleoni regarded any demand for greater equality of opportunity as inconsistent with the liberal and market-oriented framework.