This essay aims to criticize contemporary European liberalism in terms of Rawls’s hypothetical contractualism. It argues that contractualism is unable to justify legitimacy due to the irreconcilable contradiction between the individuals’ plural wills and the sovereign single will. This contradiction lies in Rawls’s hypothetical contractualism and turns his view from a Kantian comprehensive conception into an overlapping consensus. In his earlier works Rawls fails to justify legitimacy for the reason of holding a moral dualist view, but later Rawls fails again by ignoring the fragility of an overlapping consensus when the constitutional essentials are at stake. In fact, Rawls’s failures are rooted in the idea of contractualism that he shares with Hobbes and Rousseau who also entangle themselves in the same contradiction.