Although Knapp did not include the year of this letter in the dateline, from the context of the letter the editors determined that Knapp wrote it in 1858.

Lincoln traveled to Winchester on September 28, and delivered an address on September 29. For the first part of the election campaign of 1858, Lincoln often followed Douglas on the trail, delivering speeches either later in the evening after Douglas finished, or the next day. On July 24, however, Lincoln challenged Douglas to a series of formal debates. In an August 2 letter to Joseph Eccles, Lincoln noted that he believed one of Douglas’ replies indicated that “my presence, on the days or evenings of his meetings would be considered an intrusion.” This is most likely one of the reasons why Lincoln waited until September to speak in Winchester rather than speaking immediately after Douglas on August 7, as Knapp suggests above. Douglas eventually agreed to debate Lincoln, resulting in the famous Lincoln-Douglas Debates.

At the time, members of the Illinois General Assembly voted for and elected the state’s representatives in the U.S. Senate; hence, the outcome of races for the Illinois House of Representatives and Illinois Senate would decide the senatorial contest. In the local elections of 1858, Republicans won a majority of all votes cast in Illinois, yet pro-Douglas Democrats retained control of the General Assembly and Douglas ultimately won reelection. Through the campaign, however, and in particular through his participation in the Lincoln-Douglas Debates, Lincoln gained recognition as well as standing within the national Republican Party.