| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | R | 1,114 | 5,091 | 6,290 | |
| 2020 | R | 1,355 | 5,100 | 6,540 | |
| 2016 | R | 1,108 | 4,236 | 5,545 | |
| 2012 | R | 1,356 | 3,749 | 5,184 | |
| 2008 | R | 1,555 | 3,685 | 5,314 | |
| 2004 | R | 1,907 | 3,633 | 5,575 | |
| 2000 | R | 1,591 | 3,033 | 4,710 | |
| 1996 | R | 1,724 | 2,220 | 4,450 | |
| 1992 | R | 1,837 | 2,453 | 5,039 | |
| 1988 | R | 1,692 | 3,077 | 4,794 | |
| 1984 | R | 1,593 | 3,512 | 5,122 | |
| 1980 | R | 1,965 | 2,818 | 4,861 | |
| 1976 | R | 2,034 | 2,250 | 4,314 | |
| 1972 | R | 1,322 | 3,054 | 4,399 | |
| 1968 | R | 1,261 | 2,236 | 4,174 | |
| 1964 | D | 2,105 | 1,996 | 4,102 | |
| 1960 | R | 1,755 | 3,238 | 4,993 | |
| 1956 | R | 1,912 | 2,946 | 4,868 | |
| 1952 | R | 1,900 | 2,630 | 4,550 | |
| 1948 | R | 1,937 | 2,056 | 4,045 | |
| 1944 | R | 2,000 | 2,493 | 4,517 | |
| 1940 | R | 2,587 | 2,889 | 5,486 | |
| 1936 | R | 2,646 | 2,931 | 5,590 | |
| 1932 | D | 3,150 | 2,963 | 6,136 | |
| 1928 | R | 1,886 | 3,641 | 5,532 | |
| 1924 | R | 2,052 | 2,152 | 4,424 | |
| 1920 | R | 1,823 | 2,552 | 4,387 | |
| 1916 | R | 1,180 | 1,524 | 2,725 | |
| 1912 | D | 875 | 869 | 2,115 | |
| 1908 | R | 996 | 1,503 | 2,542 | |
| 1904 | R | 850 | 1,280 | 2,188 | |
| 1900 | R | 1,000 | 1,329 | 2,377 | |
| 1896 | R | 929 | 1,153 | 2,095 | |
| 1892 | R | 690 | 752 | 1,635 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Estill County, nestled in the foothills of the Cumberland Plateau, recorded an R+63.2 presidential margin in 2024, reflecting a decades-long partisan realignment that has made this former swing territory among the most reliably one-sided in the state.
The Democratic margin in Estill County peaked at three points in 1932. By 1968 the county had flipped, voting Republican for the first time in many years. The 2024 margin was sixty-three points, the most Republican-leaning result in the county's modern history.
The economic context is the key. Estill County's median household income of $46,051 sits well below state and national norms, and 21% of residents live below the federal poverty line. The shift here is part of a broader realignment of working-class places across the country. The county's voting pattern over the last decade is most similar to that of Wayne County and Tipton County.