Despite libertarianism’s political popularity, tax scholarship is largely silent about the interaction between libertarian principles and the structure of our tax system. To fill that gap, this Article mines the nuances of libertarian theory for insights into one feature of our tax system—the charitable tax subsidies—and finds some surprising insights. Although one strand of libertarianism suggests that charitable tax subsidies are in and of themselves illegitimate, several other understandings of libertarianism see a role for the state to engage in a varying amount of redistribution or to provide varying amounts of public goods. Surprisingly, some readings even lend weight to the common criticism that the charitable tax subsidies do not do enough to assist the poor and disadvantaged. Only a lenient interpretation of classical liberalism that conceives of a vibrant non-profit sector as a public good in and of itself and an expansive reading of left-libertarianism support something akin to our current structure, in which elite cultural institutions such as the opera are subsidized even if they provide no free or discounted services to the poor. In addressing these questions, this Article rounds out a series on the interaction of distributive justice and the charitable tax subsidies.