Freedom's tally: An African American business in the Jim Crow South
With Taylor gone, Cotton joined the Great Migration of millions of African Americans leaving the South after World War II for better opportunities in the North. With an eye toward opening his own store in Chicago, he enrolled in the Chicago School of Shoe Rebuilding in 1950, earning his degree in hat cleaning and repair. Soon afterwards, Cotton received a long-distance phone call from North Carolina. The man who had bought Bob’s Hat Shop was gravely ill and his sister needed someone familiar with the business who could also clean and repair hats. Eventually, the sister let Cotton take over the payments, and by 1953, Cotton had taken possession of the business free and clear.

While the protests targeting the Woolworth’s down the street were escalating, an African American Marine walked into Bob’s Hat Shop and asked for a shine. In that moment, with history being made up the street, Cotton made the decision to desegregate his store. He told the soldier to have a seat—in one of the chairs reserved for white customers only. After his customer paid the bill and left, Cotton turned to an understandably stunned friend and announced that “from now on anybody that comes in here can get on the stand. I don’t care whether they close us up or not.” To desegregate his store in 1960, when the successes of the civil rights movement were still uncertain, took considerable courage. The landscape of the past is studded with the graves of men and women who had similarly challenged Jim Crow.
The bedrock of the local economy of African American communities in towns like Greensboro comprised of small business owners and entrepreneurs like Robert Taylor and Harold Cotton. The overlooked and unseen labor of the black proprietors of hat shops, beauty salons, funeral parlors, photography studios, barbershops, and other businesses performed the yeoman’s work of sustaining the African American community through the decades of Jim Crow.
Harold Cotton's story is one of two biographies featured in Black Main Street: Funding Civil Rights in Jim Crow America, a temporary display within the American Enterprise exhibition's "New Perspectives" case, on view from September 16, 2016 through March 8, 2017.
Jay Driskell is a historian of the urbanizing, segregating South. He is the author of Schooling Jim Crow: the Fight for Atlanta’s Booker T. Washington High School and the Roots of Black Protest Politics.