Prior to their arrival in Chicago, blacks experienced legally enforced de jure segregation. In the Jim Crow South, laws mandated such things as separate seating for blacks on streetcars and separate schools for black children. These formal laws did not exist in Chicago as they did in the South. But informal laws and invisible habits encouraged the de facto separation of blacks from whites. Most notably, The Chicago Real Estate Board perpetuated segregation by encouraging white Chicagoans to employ racially restrictive covenants. The covenants were privately enforced legal agreements among property owners that prohibited the sale of real estate to black buyers. At one point, nearly eighty-percent of Chicago real estate was under restrictive covenant.
Despite formidable obstacles, blacks still believed life would improve once they established roots in the segregated neighborhood known as the “Black Belt.” By 1919, the Black Belt comprised about thirty contiguous blocks on the South Side. As the black population expanded, tensions increased with whites in neighborhoods adjacent to the Black Belt that resisted integration. With the Black Belt, the inability to expand caused severe problems. The poorest migrants lived in uninhabitable, dangerous, and severely overcrowded houses that lacked modern plumbing and heating. More prosperous residents of the Black Belt, known as “the old settlers,” resented their inability to escape “ghetto” conditions created by the new arrivals. The “old settlers” considered the migrant’s southern ways an embarrassment to the race. To improve behavior among the migrants, the editor of the Chicago Defender considered Robert Abbott published rules and regulations for proper conduct in public places. For all their prim and proper recommendations, Abbott and the old settlers could not inhibit the conduct of newly arrived migrants who delighted in their freedom from supervision by whites.
“Old settlers” especially could not deny the appeal of “The Stroll.” Located on State Street between 26th and 39th Streets, The Stroll was among the most vibrant entertainment districts in the United States. To many migrants, The Stroll presented opportunities to reconstruct black culture in a new urban environment where the New Negro could live free from white supervision.