This article will explore whether a classical conservative should favor radical tax reform, or should instead favor a continuation (perhaps with some moderate reform) of the current progressive federal income tax system in place since 1913. Part II of this article will begin the discussion with an overview of classical conservative thought. Part III will then briefly examine both the current progressive federal income tax system and the alternatives put forth by radical reform groups. Part IV will then analyze the differences between the current system and the radical reforms through the prism of classical conservative thought. Part V provides concluding thoughts.