The editors conjectured the date from the letter’s content and Lincoln’s delivery address. Ray is writing Lincoln during the Lincoln-Douglas Debates. Lincoln was the Republican candidate from Illinois for U.S. Senate in 1858. In the summer and fall of that year, Lincoln and his Democratic opponent, the incumbent Stephen A. Douglas, held a series of seven debates throughout the state. During the first debate in Ottawa, Illinois, on August 21, Douglas challenged Lincoln to answer a series of questions, including if Lincoln would vote to abolish slavery in the District of Columbia if elected. On August 23, Lincoln wrote Ebenezer Peck and Norman B. Judd asking them to meet him in Freeport, Illinois, the site of the second debate, to discuss how to cope with Douglas’s tactics introduced at Ottawa. The fact that Ray wrote this letter in response to Douglas’s questions at Ottawa and addressed it to Lincoln at Freeport suggests that he intended for Lincoln to consider these talking points ahead of the second debate at Freeport on August 27. See the 1858 Illinois Republican Convention; 1858 Federal Election.

While Lincoln answered Douglas’s earlier question about slavery in the District of Columbia during his speech at Freeport, he made no use of Ray’s suggested “Real Popular Sovereignty” rhetoric. Instead, Lincoln indicated that while he personally favored abolishing slavery in the district, he would only vote for it if three conditions were met: that the abolition be gradual; that a majority of voters approve it; and that “unwilling owners” be compensated for the loss of enslaved persons. Lincoln did, however, take an opportunity to question Douglas’s commitment to popular sovereignty. He posed four questions concerning the admission of Kansas to the Union and the expansion of slavery. In his second question, Lincoln asked Douglas whether the people of a territory could, in light of the Dred Scott decision, “exclude slavery from its limits prior to the formation of a state constitution?” Douglas responded by establishing what became called his “Freeport Doctrine.” Douglas answered yes, citizens could exclude slavery by local legislation. “Slavery cannot exist a day or an hour anywhere,” Douglas famously retorted, “unless it is supported by local police regulations, furnishing remedies and means of enforcing the right to hold slaves.” Douglas’s Freeport Doctrine resolved the inconsistency between popular sovereignty and the Dred Scott decision on a practical level, thereby satisfying his Illinois supporters, assuring his reelection to the Senate, but denting his chances in the American South in the presidential election of 1860.