Henry M. Mathews holds an academic background from prestigious institutions, including the University of Virginia and Lexington Law School. He began his career in the military, serving in the Confederate States Army, where he held various roles culminating in a chief of department position during the Vicksburg Campaign. Following his military service, Mathews transitioned to a leadership role in the private sector, serving as president of the White Sulfur Springs Company. His career demonstrates a progression from military leadership to executive management in the private sector.

Henry M. Mathews's political identity is marked by an intriguing blend of progressive economic policies and a pragmatic approach to governance. He championed industrial growth and infrastructure improvements while simultaneously appointing Republicans to key positions, showcasing an ideologically flexible stance. Mathews's early advocacy for a state immigration bureau and state geological surveys indicates a forward-thinking economic strategy. His decision to call on federal troops during the Great Railroad Strike of 1877 reveals a calculated approach to civil defense, balancing state interests with federal authority. Despite mixed historical assessments, Mathews's political maneuvers suggest a nuanced, non-partisan strategy.