For almost four decades preceding the 1787‐88 ratification debates — during which American Federalists drew severe criticism from the Anti‐Federalists — Enlightenment politics in Europe had been undergoing equally severe criticism from Jean‐Jacques Rousseau. Though largely unaware of each other, both of these critics advanced distinctive republican theories based on civic virtue and individual liberty. Rousseau argued for a republic which would require the near‐total alienation of retained natural rights, abstention from bourgeois commerce, and complete conformity to the general will. The Anti‐Federalists, by contrast, envisioned a republic based on retained natural rights, one that would reconcile the communitarian spirit of antiquity with the commercial values and individual rights of modernity. By comparing and contrasting the most salient features of these contending visions, whose theoretical trajectories are — I argue — crucially opposed, we can glimpse the inherent conflicting requisites of republican government and therewith some of the enduring dilemmas of republican theory.