Lincoln arrived in Freeport for the second of seven Lincoln-Douglas Debates at nine a.m. on the morning of Friday, August 27 via the Illinois Central train. He arrived from Amboy, approximately fifty miles south of Freeport.

Lincoln was the Republican candidate from Illinois for the U.S. Senate. He ran against, and lost to, Democrat Stephen A. Douglas, the incumbent. See 1858 Illinois Republican Convention; 1858 Federal Election.

Republicans, including Lincoln, opposed the decision in the Dred Scott case, which effectively barred any current or future emancipated slave from the right of United States citizenship and solidified the right of American citizens to transport their property wherever they wished—including taking an enslaved individual into a free state—without feared loss of that property. The outcome essentially invalidated the concept of popular sovereignty, which Stephen A. Douglas argued allowed territorial and state governments to either allow or prohibit slavery as they saw fit. Lincoln’s main concern with popular sovereignty had been its power to “allow the people of a Territory to have Slavery if they want to, but does not allow them not to have it if they do not want it.” The Scott decision proved Lincoln’s assertion, to which he remarked, “as I understand the Dred Scott decision, if any one man wants slaves, all the rest have no way of keeping that one man from holding them.”