The earliest notice of these Indians is found in the Hernando de Soto's narratives in 1540. Though this encounter would end in a bloody battle, as the brutalities of the expedition became known,  the Choctaw would come to embrace European traders nearly two centuries later.

When the French, in the beginning of the 18th century, began to settle colonies at Mobile, Alabama; Biloxi, Mississippi; and New Orleans, Louisiana, they befriended the Choctaw, who became their allies in wars against other Indian tribes. Though the Choctaw were closely related to the Chickasaw tribe in language and customs, they were constantly at war with them.

Later, English traders succeeded in drawing over to the English interest, some of the eastern Choctaw towns, which brought on a war within the Choctaw, with those who were still loyal to the French. This animosity continued until the French and Indian War was over in 1763. After the French had surrendered their American possessions to Great Britain, and to some extent previously thereto, members of the tribe began to move across the Mississippi River.

During the American Revolution, most Choctaw supported the Thirteen Colonies' bid for independence from the British Crown. By the time President George Washington initiated a program to integrate Southeastern Indians into European American culture following the American Revolution, many Choctaw had already intermarried, converted to Christianity and adopted other white customs.

Over the next several years, the Choctaw would enter into nine treaties with the U.S. Government, the last three of which were designed to move the Choctaw west of the Mississippi River. During the Indian Removal Period, President Andrew Jackson made the Choctaw exile a model of Indian removal. In 1831, nearly 17,000 Choctaw became the first Native Americans to walk the Trail of Tears to Indian Territory (Oklahoma.)  Nearly 2,500 members perished along the way.

The last treaty; however, also provided that Choctaw members could choose to stay in Mississippi and become U.S. Citizens, subject to the laws of the country and the state. Approximately 5,000-6,000 chose to remain, but would suffer legal conflict, harassment, and intimidation at the hands of the white settlers.

The Choctaw in Mississippi were later reformed as the Mississippi Band of Choctaw Indians and the removed Choctaw became the Choctaw Nation of Oklahoma.

The Choctaw were removed west of the Mississippi River starting in

 1831, painting by Alfred Boisseau, 1846.

Despite the many lives lost on the Trail of Tears, the Oklahoma Choctaw remained a hopeful and generous people. The first order of business upon arriving in their new homeland was to start a school and a church and drafted a new constitution.

During the Civil War, the Choctaw in both Oklahoma and Mississippi mostly sided with the Confederate States of America. At the beginning of the war, Albert Pike was appointed as the Confederate envoy to Native Americans. In this capacity he negotiated several treaties, including the Treaty with Choctaw and Chickasaw in July 1861.

Some Choctaw identified with the Southern cause and a few owned slaves. In addition, they well remembered and resented the Indian removals from thirty years earlier and poor service they received from the federal government.