The Industrial Revolution witnessed an increase in wealthy entrepreneurs who were also philanthropists. During this era, James Buchanan (Buck) Duke and Richard Joshua (R.J.) Reynolds led the tobacco production industry in North Carolina. These industrialists and their families became active agents in defining southern Progressivism and modern philanthropy during the twentieth century. Southern philanthropy differed from the North. Northern philanthropists donated their wealth at home and abroad, while southern philanthropists contributed to the social welfare of their communities and regions. In addition, politics in the South created a unique opportunity for these industrialists to become paternalistic leaders in their respective communities. Legal segregation in the South also limited the impact of the industrialists’ philanthropy. However, unlike some of their fellow southern industrialists, the Duke and Reynolds families contributed to African American causes. This study demonstrates the key role that the Duke and Reynolds families played in the development of their respective cities and the Piedmont region, as well as their role in improving social welfare. Examining these cities and the region through the intersection of business, politics, and philanthropy explains the relationship between company growth and urban development. The legacies of these families are evident today through their former companies, as well as universities and organizations they established.