Reuben May was born in 1815 in Robinson Creek, Pike County, Kentucky. He spent his early years in Kentucky before relocating to Clay County and eventually Wisconsin. May's career began with a stint as a postmaster and later transitioned into military service, where he distinguished himself during the Civil War. Post-war, May entered the political arena, initially serving in the Wisconsin State Assembly and later making unsuccessful bids for higher offices. His professional expertise lies in military leadership and public service, with a notable focus on economic policy reform through his involvement with the Greenback and Union Labor parties.

Reuben May's political identity is marked by his advocacy for the Greenback Party, which sought monetary policy reform through the issuance of unbacked paper currency. His support for compulsory education standards, while opposing the English language requirements in the Bennett Education Law, reveals a nuanced stance on educational policy. May's legislative history shows an unexpected convergence with opposing factions on environmental regulations, suggesting a highly calculated approach to protecting regional industrial interests. His varied political affiliations and candidacies, from the Greenback to the Union Labor party, illustrate an ideologically agile approach, constantly recalibrating to align with evolving economic and social issues.