The fundamental issue of freedom came down to the idea of convictions and beliefs in the Lincoln- Douglas Debates. Douglas advocated the practical idea that popular sovereignty was best suited to express the issue of freedom. Douglas made the argument that the idea of freedom is embodied by citizens of a particular region being able to determine their own notion of freedom and their own ideas of how their government should be constructed. This was a politically expedient viewpoint in which convictions and beliefs can essentially be bargained away through popular sovereignty. For Douglas, it was completely consistent with principles and ideas of freedom if Illinois was not a slave territory and Missouri was. This is consistent with Douglas' definition of freedom if popular sovereignty determined both states' realities.
For Lincoln, the issue appeared more complex and simultaneously more simple. Lincoln believed that the issue of slavery existed antithetical to the premises of democracy. Popular sovereignty, he argued, is not going to solve the problem because the problem will never be resolved as long as the nation remains "half slave" and "half free." Freedom for Lincoln was being able to have the nation represent the promises of its own democratic charter set forth in the Constitution. Lincoln argued that there cannot be freedom in the current set up because the definition of "slave" and "free" as being defined from state to state negated some element of the Constitution. Lincoln was mindful not to move towards an abolitionist point of view and did not embrace the idea of political and social equality for people of color, but he did view the issue of slavery and the idea of popular sovereignty solving it as fundamentally challenging to freedom because, as an absolute, it was being negotiated and practically viewed as opposed to being revered as an absolutist principle.
Throughout the debates, this basic difference was revealed. Armed with popular sovereignty, Douglas advocated freedom as being an issue of statehood choice. Lincoln argued that freedom is transcendent and cannot exist with a system that is contingent across state borders. This becomes their fundamental point of views towards freedom brought out in the debates, where Douglas voiced practicality and Lincoln a transcendent idea. Douglas gained short term political benefit, while Lincoln became the more historically revered figure for his belief system.