I argue that Tomasi’s most fundamental “bleeding heart libertarian” insights are not adequately served by Rawls’s lexical framework and his idealized theory of institutional choice. Perhaps paradoxically, using Rawls’s lexical framework to articulate Tomasi’s declared concerns for both economic liberty and “social justice” gives the latter concern very little weight. For that reason, Tomasi’s own objections against classical liberalism would ultimately apply to his own positive contribution as well: the satisfaction of a distributional adequacy condition is secured on purely contingent (...) grounds. Furthermore, Tomasi’s endorsement of Rawls’ conception of the first tasks of political philosophy might render his case for laissez-faire forms of capitalism immaterial. This is because Rawls fails to appreciate the very narrow theoretical relevance of identifying institutional arrangements purely as a matter of “ideal theory”. Feasibility concerns have always been an important element in the classical liberal critique of interventionist and redistributive politics. Yet they have invariably failed to be featured, in any theoretically prominent way, within the most philosophically oriented defenses of the classical liberal order. A formulation of bleeding heart libertarianism along Rawlsian lines would be equally wanting in this regard. (shrink)