Windbreaker for Sharecroppers touches on a recurrent interest in agrarian life that Brown would revisit throughout his career. "Windbreaker" in the title refers to the lines of trees, planted in dense lines to protect farms from turbulent wind, here dividing the plots of several family farms. Sharecropping is the practice of a landowner leasing land to farmers in exchange for a share of the farm's products- an arrangement which can be more detrimental than beneficial for the farmers, who may struggle to meet quotas in bad years. Sharecropping has a long history in the American South, where it was especially widespread following the end of the Civil War, often under terms that would abuse and prey upon Black farmers. A massive, monolithic building on the horizon overlooking the barren plots of land indicates Brown's concern for the system's abuses, a theme he would later revisit in a number of 1980s pieces comparing aspects of contemporary American life to feudal European systems with nobility and serfs.