Reuben May's background is marked by a blend of military service, political involvement, and leadership in various capacities. He began his career in the Kentucky Militia, rising to lieutenant colonel during the Mexican–American War. May transitioned to the Union Army during the Civil War, where he organized and commanded infantry regiments, demonstrating significant leadership in key battles. After the war, he pursued a political career, holding various positions in state assemblies and running for higher offices, including governor, under different party affiliations. May's professional expertise spans military leadership, public service, and advocacy for economic policies, particularly those favoring expanded money supply and opposing the gold standard.

Reuben May's political journey reveals a complex ideological fluidity, oscillating between Democratic and Republican affiliations while advocating for the Greenback and Union Labor parties. His military leadership during the Civil War underscores a steadfast commitment to Union loyalty, yet his economic policy positions, particularly his support for expanding the money supply and opposing the gold standard, reflect a non-traditional alignment. May's rhetorical style seems to embrace calculated policy convergences, as seen in his support for compulsory education without English language requirements, hinting at a nuanced approach to regional interests.