His grandfather, Joseph C. Hutcheson, was one of the county's largest landowners and a justice of the peace, although he lost his one attempt at election to the Virginia House of Delegates (in 1855).
Young Sterling was named for a great-uncle, Col. Charles Sterling Hutcheson, a plantation owner who served one term as a Whig in the Virginia House of Delegates, then became the county's circuit judge and raised a regiment for the Confederate States Army during the American Civil War, and after receiving a pardon from President Andrew Johnson, remained in Mecklenburg county to care for a disabled son (also C.S.
Congressman and leading citizen in Houston, although his eldest son, lawyer and CSA Captain John William Hutcheson, died of wounds received defending Richmond at the Battle of Cold Harbor.
Shortly before Judge Way's final illness, he had ruled against a black fireman working for the Norfolk Southern Railroad, and who had sued the Brotherhood of Locomotive Firemen & Enginemen for excluding blacks from their union, but the Fourth Circuit remanded the case for further consideration of jurisdictional questions and the federal Railway Labor Act.
He also decided cases brought by black parents against the King George County and Gloucester County school boards,[7] which failed to meet the "separate but equal" standard set forth in Plessy v. Ferguson, and two years later found the board and superintendent guilty of contempt of court for failing to comply with his orders and imposed $250 individual fines, which future Justice Thurgood Marshall believed encouraging.
However, some local leaders (including his state senator brother) continued to inflame controversy for several years, which Hutcheson avoided by retiring.