Yesterday, Tyler Cowen asked "Which 20th century classic of American conservative political thought has held up best?" Ezra Klein decided to turn it around on the liberals, noting that "Rawls would seem an obvious contender, as would Susan Moller Okin." As it happens, I finished Samuel Freedman's excellent newish book Rawls -- an extended explication of the man's body of work -- recently and among other things it served to me as a reminder of how dated A Theory of Justice seems some respects.
Now don't get me wrong, I think it "holds up" perfectly well in the sense of continuing to be a vital work of political philosophy. But in another sense of "holding up" it has pretty little to say about our contemporary political debates. The main antagonist of Rawls' egalitarian liberalism is, in the book, some form of utilitarianism which just isn't at all the structure of our political arguments at all. That's not really a failing on Rawls' part as his project is his project, and not some other thing, but it is a noteworthy aspect of the situation.
Okin's Justice, Gender, and the Family by contrast seems to me to have a much more clear and direct relevance to things people argue about today. The premise that women and men deserve political and social equality is something few people would disagree with these days, but Okin shows that some surprisingly radical conclusions about the status quo can follow from that in a way that's relevant in some obvious ways to arguments that you see in the cut-and-thrust of contemporary practical political debates. Rawls has created something vastly more theoretically ambitious, but in part in virtue of that ambition it's much less clear what the actual implications are. Arguments about what sorts of policies do or do not maximize the well-being of the worst-off turn out to be extremely controversial in ways that make it extremely difficult to say what a Rawlsian take on this or that would be.