Of the questions concerning the many great minds of the European Enlightenment, the question of what constitutes right and proper government perhaps had the most enduring influence on the world stage. Both Thomas Jefferson and Immanuel Kant attempted to answer the question of what constitutes right government, in particular by basing the system upon the idea of human freedom as an inalienable right. This project is an attempt to compare the systems proposed by these two authors, as well as to critique each on its ability to protect and foster individual freedom. It is my opinion that neither manages to do what it is constructed to do, as each fails to fully protect individual freedom, and each has as part of it a component which conflicts with individual freedom.