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Choctaw County was once part of the Choctaw Nation. There were Choctaw settlements in the vicinity of Pushmataha before the Trail of Tears.
Choctaw County's early European American pioneers were largely farmers from North and South Carolina. The Alabama, Tennessee, and Northern Railroad, which ran from the north to the south through the county, connected the area with the Port of Mobile and northern Alabama in 1912. It caused a shift in population from the Tombigbee River area to the central portion of the county.
The 1920s saw a boom in the county's population, with such companies as the E. E. Jackson Lumber Company or the Choctaw Lumber Company creating jobs. During the Great Depression, the sawmill industry was destroyed. In 1944, the first oil well in Alabama was successfully drilled at Gilbertown. Oil and gas became the most important industry in the county. The 1970s saw the industry decline as well as its profitability.