The family owned thousands of acres of ranch land in southwest Virginia, built over generations, including through marriage alliances.

Congressman, had several sons, one of whom (Henry's uncle) became Confederate Civil War Cavalry Commander Jeb Stuart.

He organizing a statewide referendum for popular election of senators because his favorite candidate, Fitzhugh Lee (former governor and a nephew of Robert E. Lee) had not been selected for U.S. Senate from Virginia by the Virginia General Assembly, which instead elevated an obscure railroad attorney, Thomas Staples Martin.

However the new 1902 Constitution also instituted poll taxes and other requirements which disenfranchised many African Americans and poor whites, but facilitated the growth of the Martin political machine, which later became the Byrd Organization.

[5] Although Stuart wanted to run for governor in 1909, he acceded to Martin's advice and instead ran for U.S. Congress, but lost to six-term Republican Campbell Bascom Slemp.

He also appointed a commission that in 1919 revised the Virginia Code (for the first time in 1887), as well as enacted legislation which rationalized taxation, so local counties could tax real estate and the state other forms of property.

The bond-financed highway construction of the Virginia Turnpike System in the area before the Civil War had been disastrous, and led to many bankruptcies.