Sans Bois County was part of the Moshulatubbee District, one of three administrative super-regions comprising the Choctaw Nation.

[3] Underground coal mining was undertaken here in the early 20th century, creating jobs and attracting railroad construction to southern Haskell County.

In 1912 a large, underground explosion rocked the Number Two mine at McCurtain, killing 73 (seventy-three) miners and bankrupting the San Bois Company.

The Lone Star Steel Company became the county's leading coal producer.

The collapse of cotton prices and the Great Depression caused a drop in population as well as farm acreage.

In 1934 the Federal Emergency Relief Administration helped over 85 percent of Haskell County's population.

[3] The relatively large water area results from the presence of Eufaula Lake and the Robert S. Kerr Reservoir.

Stigler is home to the Haskell County Courthouse, which has become notable for erecting marble statues of the Ten Commandments and the Mayflower Compact on the front lawn (see Separation of church and state in the United States).

The decision by the U.S. Tenth Circuit Court of Appeals comes in a challenge filed by the American Civil Liberties Union and the ACLU of Oklahoma on behalf of a local resident.

After the court decision, the marble statue was moved approximately 600 feet east to private property.

The following sites in Haskell County are listed on the National Register of Historic Places: