As Loren Lomasky suggested in his fun and insightful essay on “Libertarianism at Twin Harvard,” it’s not hard to image Nozick’s entitlement theory leading to a “left-wing” conclusion and some version of Rawls’s justice as fairness leading to a “right-wing” conclusion, hence the attractiveness of Will Wilkinson’s “Rawleskian” synthesis and John Tomasi’s market democratic interpretation of justice as fairness.
Here is Lomasky on Twin Nozick:
Twin Nozick embarks from a (Twin?) Lockean foundation of basic rights to life, liberty, and property, arriving at what he dubs the “entitlement theory” (of justice in holdings). According to the entitlement theory, one has justifiable title to some item so long as one has come to possess it either through just original acquisition, just voluntary transfer, or just compensation by way of rectifying a prior injustice. No other criteria are needed. (See ASU, 150–53.) …
Twin Nozick begins and ends by espousing libertarianism—for a world of perfect compliance. That, most assuredly, is not our actual world. (Nor is the history of Twin Earth a much cheerier tale.) There can be no hope of unraveling the tangled skein of injustices so as to place things in the hands where they properly belong. Not only do we lack an adequate historical knowledge taking us back with no gaps to Adam and Eve/Lucy, but even if the record were complete we would not know what to do. Those who suffered wrongs in the distant past are beyond human ability to render whole; those who suffer contemporary rights violations would not even exist had their conception not been brought about through causal sequences involving yet other rights violations. In so convoluted a moral realm there is nothing for the entitlement theorist to do other than throw up her hands and admit that Humpty Dumpty is not to be put back together again. Instead, the best that can be achieved is to start over from a Day One in which people will be allowed to transact howsoever they choose from a starting point of equality. That requires in turn a Day Zero given over to radically equalizing holdings and other natural assets so that all will be equally placed on the social starting line.