The inspiration for this essay originally came from an article in the New York Times that focused largely on the conservative youth movement in America. Though the article was not generally philosophically focused, it suggested a broader question: Given the vast spectrum of conservative belief is there anything in present conservative theory that capable of capturing this new millennial conservatism? To begin by way of apology, I realize that the term millennial conservatism is not a familiar one. Though Americans may understand what it means to be Republican, neoconservative, libertarian or member of the Christian right, the concept of millennial conservatism is most certainly unfamiliar. Indeed, as far as I am aware the term is not one currently used in popular discourse-or any discourse to my knowledge. Yet I have selected it for a single purpose, as a reflection of the convergence of a youth conservative movement with a variety of varying conservatisms. Conservatism in America today has become a remarkably young movement, and yet, “conservatism in American politics is less an ideology than a coalition. It has many different flavors and strands, and there is no sense in pretending that they do not occasionally conflict with another, or tug at the fabric of the whole” (McClay 19). There is certainly a young conservative movement, but what is the force behind it, or perhaps more important, what should be? How ought we think of conservatism philosophically in looking to the next generation of conservatives? As such there is some value in looking for a conservatism capable of encompassing the intuitions of this emerging millennial movement. We would do well to accept that no one doctrine could be capable of meeting all the demands of each group. It is doubtful that young evangelicals will ever be reconciled with the Future Business Leaders of America. Yet wit this project in mind it seems prudent to look to two of the most influential conservatives of the last half-century. I have little doubt that some will dispute the relative importance of either Strauss or Oakeshott. To be sure Hayek, Kirk, Chambers, Goldwater, Buckley and Jaffa are all worthy theorists. Yet there are few theorists who have received as much attention as attention as philosophers in their own right-separate from their conservatism-as Strauss and Oakeshott.There may be others who will dispute that Strauss is conservative at all, and a number of well-respected intellectuals have presented several compelling arguments disavowing-or at least moderating-Strauss’s perceived conservatism. Although this is an objection I will address briefly in part one, it may be useful, at the outset, to offer two counterarguments. First these works often functions more as Straussian apologies than legitimate refutations of his conservatism. Second, given Strauss’s widely recognized conservative influence, it is only sensible to presume that not everyone has gotten it wrong. That is, that the consistency with which Strauss has been associated with conservatism is not mere coincidence. Thus the following essay will constitute an attempt to understand two competing conservatisms, and the contributions they stand to make to the millennial conservative movement. In looking both to Strauss and Oakeshott I will attempt to discern what we can take from their philosophies, and eventually which we have reason to prefer. As such the essay will be organized in three parts: Part one will examine Strauss and his conservatism of Natural Right. I will then proceed, in part two, with a discussion of Oakeshott’s dispositional (as well as traditional and libertarian) conservatism. Finally, and by way of conclusion, I will briefly discuss the relative merits of each conservatism in part three.