By 1914 he becomes a sergeant in the First Richmond Howitzers, under Captain Jeb Stuart III. As part of the Army of Northern Virginia, Featherston fights on the Susquehanna River and then falls back towards Maryland. During this time he reports his suspicions to an intelligence officer about Pompey, Captain Stuart's manservant, being a Marxist rebel. Pompey is protected from investigation by his prominent master, however, and reveals himself as a real Marxist when the Negro uprisings break out. Featherston allows Negro workers to serve an artillery piece to repel a US attack. The Negroes themselves are even enthusiastic about serving with Featherston, commenting they would have helped him defend the position even if it came down to using pistols. Indeed, when first introduced, Featherston is in many ways a sympathetic character and his attitude towards Blacks is rather ambiguous - far from the fanatic, genocidal hatred he would develop towards them in later parts of his career.