Owing to its history of Yankee anti-slavery settlement in “Bleeding Kansas” days, Riley County became rock-ribbed Republican following Kansas statehood, except when over half of its voters supported Progressive Theodore Roosevelt in 1912 who himself was a Republican who had broken away from the party in that election cycle. Being relatively resistant to the Democratic populism of William Jennings Bryan, Woodrow Wilson and Franklin D. Roosevelt, Riley County stood as the westernmost of thirty-eight US counties to have never voted Democratic for President since the Civil War. However, it was the only one whose status as “never Democratic” stood significantly threatened in 2016 and 2020: Hillary Clinton’s losing margin of only 3.5 percent was the second-closest any Democrat has come to claiming the county behind her husband in the divided 1992 election.