Henry L. Hess spent several years in the Oregon State Senate, representing Union and Wallowa counties as a Democrat. He later pursued the governorship, winning the Democratic primary in 1938 but losing the general election. Hess then dedicated nearly a decade to public service as the U.S. Attorney for the United States District Court for the District of Oregon. His professional background is complemented by his personal life, having married Madeline Mae Owsley in 1964.

Henry L. Hess's political career reveals a strategic blend of progressive economic advocacy with an unexpected alignment on certain conservative governance issues. His support for New Deal policies juxtaposed with his state-level legislative efforts hints at a nuanced approach to federalism. Despite his Democratic roots, Hess's legal tenure as U.S. Attorney suggests a pragmatic yet principled stance on law enforcement. His political maneuvers, especially in the 1938 gubernatorial race, demonstrate a calculated effort to balance regional interests with broader ideological commitments.