This paper argues that the diversity of conflicting comprehensive doctrines in liberal pluralist societies raises a problem of estrangement between citizens and the basic structure of society that Rawls' version of political liberalism does not successfully solve. 'Political estrangement' occurs when someone refuses to accept a political outcome that favors a comprehensive doctrine she rejects, based on what she imagines, correctly or incorrectly, to be true of her fellow citizens' comprehensive doctrines and their effect on political outcomes. Rawls argues that (...) the political conception of justice and the use of public reason ensure the incompatibility of our comprehensive doctrines will not undermine our willingness to to accept political decisions contrary to our own values. However, public reason does not guarantee this result. Imagination can allow us to see that the influence of some reasonable comprehensive doctrines can lead to oppressive political outcomes and public reason restricts us from addressing this fact. Yet, widening public reason to account for this problem is likely to increase the conditions that cause estrangement. The paper concludes that the political conception of justice and public reason may sometimes fail to adequately justify political outcomes in the sense Rawls hopes. (shrink)