The authors analyze in a comparative context some aspects in the evolution of political, educational and legal values in Greek antiquity, the Hellenistic period and in the contemporary world. Are highlighted the similarities and differences in the historical context of these values. The contradictory character in the evolution of values is examined, i.e. the fact that positive values (democracy, freedom, justice, truth, morality, faith, etc.) coexist with their antipodes (tyranny, slavery, inequity, falsehood, amorality, arrogance). This creates multiple confusions and difficulties in the sphere of social life. Thus, in conclusion - the contradictory evolution of the mentioned values represents a dialectical relationship between perennial (truth, beautiful, good) and what is variable depending on the era (behavior, political structures, legislative content, aesthetic tastes, educational methodologies, etc.).