In 1940 Atlanta, the color line between black and white citizens was clearly drawn. This color line not only kept blacks and whites apart physically, but it also prevented blacks from attaining educational opportunities, economic equality, healthcare services, and many other public amenities readily available to white citizens. Most people, black or white, did not cross the proverbial color line. Yet, in 1940, in the heart of the segregated South, one black citizen did reach across the color line, and found a white fellow citizen willing to do the same. In 1940, Benjamin E. Mays became president of the historically black, all male, Morehouse College, and was faced with the difficult task of saving the institution from financial ruin. Mays went to work soliciting monetary donations from the wealthy black and white residents of Atlanta. One particular resident, Margaret Mitchell, had recently acquired fame and fortune. The correspondence between Mays and Mitchell presented in this article highlights an association between two people who went against the expectations of their group in society-crossing racial barriers-for moral reasons that had far-reaching and long-lasting impact. The letters and their significance in the Jim Crow era, will bring home for students the impact that individual actions can have in creating change. The letters reveal specific challenges of segregation, such as medical care, educational opportunity, and the role of women.