American political theorist Judith Shklar's idea that "cruelty is the first vice" had a direct impact on Richard Rorty, a philosopher of Neo-pragmatism who applied it to literary criticism and made an illuminating interpretation on Nabokov's and Orwell's novels. Based on this, an in-depth study of the ideological connection between Shklar and Rorty as liberals will help us not only grasp Rorty's Neo-pragmatism in terms of philosophical logic, political concerns and the strategy of discourse, but also launch a new discussion on the eternal topic of the relationship between literature and morality.