Rousseau’s political thought has been accredited with major influence upon subsequent radical democratic thinking, but in fact its contradictions and obscurities render the real import of its legacy deeply ambiguous. This article aims to identify its central message through clarification of the Social Contract’s presuppositions and prescriptions, interpreted in the light of his other writings. Although the modernity of his thought is evident in the priority he gives to individual freedom, Rousseau’s disturbing novelty lies in his belief that this can only be reconciled with the interests of political community when people are, by contemporary standards, severely underdeveloped in their individuality. For him, modern socialization irreversibly blocks this reconciliation and compounds the oppression of individuals by distorting their authentic identities. Thus, Rousseau ought to be seen as offering nothing but a critique of any aspiration to salvage genuine liberty in society now. The article urges a redefinition of his contribution to political thought and depicts him as an early articulator of powerful challenges to the main aims of contractarian and democratic theory, which the latter is still unwisely apt to ignore.