After reconstruction, the transitional period immediately following the Civil War, a slow and steady stream of African Americans began leaving the South for the North and the West. A bigger exodus, known as the "Great Migration," began with World War I. Increased mechanization in farming left sharecroppers with little to do. But with its booming cotton economy, the Mississippi Delta still attracted a steady influx of migrants from the rest of the South. At its inception, sharecropping in the Delta held the promise of a decent standard of living and independence. In theory, with a good harvest, everyone stood to make money.

In reality, planters exploited the system to their advantage, and sharecroppers often wound up in debt at the end of each year. With no income during the off season, croppers were forced to buy food, clothing and other necessary supplies on credit from the plantation commissaries. Prices were exorbitant, goods were shoddy and debt piled up. When harvest time came around, tenants were often forced to sell their share of the crop directly to the plantation at below market prices. After the harvest, the tenants often failed to earn enough to cover their debts. While Delta planters enjoyed great prosperity, their tenants were stuck in an endless cycle of debt. As plantations consolidated and centralized, what little opportunities for advancement the croppers once had slipped away. Entrenched in poverty, sharecroppers began heading north for industrial jobs.

Grinding poverty was not the only reason African Americans left the Delta. In the 1920s, the threat of racial violence loomed over the South. The law in the Delta had never offered much protection for African Americans. But with the rise of the Ku Klux Klan in the 1920s, the violence and intimidation only intensified. In fact, there were far fewer lynchings in the Delta than in the rest of the state, but this provided little solace for the Delta African American community, who still lived in fear of mob violence and lynchings.

Migration was also spurred on by the lack of educational opportunities in the Delta. While the Percy family had ensured that African Americans in Washington County had access to decent education, this wasn't the case in the rest of the Delta. White school boards seldom hired enough teachers for African American students, and the teachers they did bother to hire were almost never college graduates. In one county, there were only three teachers for a population of 350 students. During the harvest season matters only got worse. Across the Delta officials refused to open schools until every last bit of the harvest had been brought in. At times, schools didn't open for the year until mid-November.

After the Great Flood of 1927, there was less reason than ever to stay in the Delta. Homes were destroyed, possessions were gone and crops were ruined. One Greenville sharecropper put it succinctly when he explained that he had to "get my famaly out of this cursed South land..."

Leaving, however, was easier said than done. Delta planters' fortunes depended on African American labor, and they were determined to keep tenants on their plantations. While some offered better conditions to induce sharecroppers to stay, others resorted to intimidation and brute force to keep tenants from leaving. Tenants wishing to leave generally slipped away under the cover of darkness, not telling anyone of their plans, lest word spread to the plantation house. Train stations were guarded and African Americans found on trains were pulled off and sent back to their plantations. To escape, croppers fleeing the Delta often walked ten or more miles to board a train in another town.

For African Americans, the favored destination was Chicago. From 1920 to 1930, the African American population exploded in Chicago, increasing from 109,458 to 233,903 residents in just a decade. The Great Migration of people was accompanied by a musical migration; Delta blues music travelled to Chicago and put down new roots in the city. Although the North was no promised land, conditions were better for African Americans, and migrants who left seldom returned.