[1] The county was organized in 1874 during the Reconstruction era; the biracial legislature named it after Massachusetts statesman Daniel Webster.

In 2018 the legislature passed a bill allowing the transport of alcohol through even dry counties in the state.

This territory had been acquired in 1833 by the United States from the Choctaw in the Treaty of Dancing Rabbit Creek.

After Indian Removal, Choctaw County was inhabited primarily by European-American settlers from Alabama, Georgia, and South Carolina, and enslaved African Americans whom they brought with them or purchased as laborers.

In the early years Greensboro was thriving, with several types of stores and shops, as the county seat was a trading center for the agricultural district.

Part of the Mississippi frontier, Greensboro had the reputation of a rough and lawless town; many notorious criminals and murders were located there.

John A. Murell, a famed outlaw of the Natchez Trace, was tried and convicted of horse stealing.

[citation needed] As the county seat, Greensboro sometimes received political candidates running for office.

For instance, in 1851 the young Jefferson Davis came seeking voters to support him in his campaign for governor.

[citation needed] At the outbreak of the American Civil War, seven young men of Greensboro and Choctaw County rushed to enlist.

His older brother, physician John Ransom Brantley, had been killed in Gonzales, Texas in 1859.

Their younger brother Arnold Brantley was shot and killed near Greensboro on August 16, 1870; his murderers escaped.

Greensboro, which had already begun to decline after the first shift in the county seat, rapidly lost population after this change.

On July 1, 2018, the legislature passed Mississippi House Bill 192, legalizing transport of all alcohol, by persons 21 and older, through dry counties within the state, and ending such actions.