Henry Carter Stuart was named after two of his famous ancestors, Patrick Henry, and “King” Carter. He was born in 1855 in Wytheville, Virginia where his father was working with the bank. Honoring the family affiliation with Emory and Henry College, Henry got his undergraduate degree there, and then moved on to the University of Virginia Law School. A financial depression hit the country in the 1870s and Henry's father, William Alexander Stewart, suffered significant financial losses. Henry quit law school to return home to help his family recover their financial position. 

           Henry's father died in 1893. The Stuart empire in Russell County grew greatly under Henry's leadership. As a child he had initially lived in the Thomas Price Mansion, but as an adult he moved to the old Thomas Hendrick’s mansion of 1806 at the Elk Garden Mill. After building West Rosedale he moved there.  Henry showed no great interest in politics, but in 1893 did serve on the Russell County Electoral Board. 

          The Stuart family connections got Henry involved in state politics. Fitzhugh Lee, the nephew of Robert E Lee, had been a General under the overall command of Henry's uncle, Jeb Stuart. Fitzhugh Lee had recaptured the governor's mansion from the reconstruction Republican Party, and was running for the national Senate. At this point in time Senators were elected by the General Assembly. A relatively unknown C&O Railroad attorney named Thomas Martin was able to capture the county courthouse political machinery traditional of the governing elite of Virginia, and with the aid of significant sums of railroad money, was elected Senator.  This greatly upset the former Confederate ruling class in the Commonwealth, and the state Democratic Party split into two factions. Thomas Martin rapidly converted his political organization into a very strong political machine, which controlled the electoral process in Virginia for many years.  Stuart started a drive in favor of the popular election of United States Senators, an effort that succeeded. 

           Henry had incorporated the family’s farming interests into the Stuart Land and Cattle Company, which was the largest cattle farm east of the Mississippi. This circumstance automatically made Henry popular with the farming class of the Commonwealth. The state Democratic Party further divided along lines with one faction supported the farmer’s interests, and the other those of the railroads. It is natural that the Martin machine ran interference for the railroad interests. In 1901 the Commonwealth undertook the rewriting of the state constitution, a process that was finished in 1902.