James Henry Dooley (January 17, 1841 – November 16, 1922) was a Virginia lawyer, business leader, politician, and philanthropist based in Richmond during Reconstruction and the Gilded Age.

Soon after, James and his brother John enlisted in the Confederate Army, joining their father's unit, the First Virginia Infantry.

After the war, Dooley completed a Master of Arts degree at Georgetown, then returned to Richmond.

Dooley also invested in real estate and became involved in railroads, insurance,[3] steel, and banking.

In 1880, Dooley joined the board of directors of the Richmond and Danville Railroad, which soon expanded into a multi-state system of over 8,000 miles.

[4] During this period of expansion Dooley served on the board of directors of the Richmond and West Point Terminal Railway and Warehouse Company.

His father (the original Major) had supported St. Joseph's Orphanage; his brother John attended Georgetown Seminary but died in 1873 before ordination; and his sister Sarah entered the Visitation monastery in Richmond.

Today, Maymont is a major Richmond attraction on the James River, with a museum, formal gardens, native wildlife exhibits, nature center, carriage collection, and children's farm and petting zoo.