The Dooleys of Richmond is the biography of two generations of a dynamic and philanthropic immigrant family in the urban South. While most Irish Catholic immigrants who poured into the region in the nineteenth century were poor and illiterate, John and Sarah Dooley were affluent and well educated. They brought sophistication and capital to Virginia, where John established one of the largest hat manufacturing companies in the United States. Noted for their business acumen and community service, the Dooleys became leaders in business, education, culture, and politics in Virginia. A bellwether of the South during these tumultuous times, the Dooleys' fortunes would rise and fall and rise again.

Mary Lynn Bayliss recounts the family’s history during their prosperous antebellum years, John and his sons’ service in the Confederate army, John’s exploits as leader of the Richmond Ambulance Committee, and the loss of the entire Dooley retail and manufacturing operations during the final days of the Civil War. After the war the Dooleys’ son James, a leading Richmond lawyer and philanthropist, devoted half a century to developing railroad networks across the United States, and became a key figure in the industrialization of the New South. He and his wife, Sallie, built Maymont, the famed Gilded Age estate that remains a major attraction in Richmond. The story of the Dooleys is a fascinating window on southern society and the people who shaped its grand and turbulent history.