Jacob S. Coxey Sr. began his career in manual labor at a young age, starting as a water boy in an iron mill. He later transitioned into entrepreneurship, partnering with his uncle in a scrap-iron business and eventually purchasing a farm and establishing a quarry in Ohio. Coxey's professional expertise evolved from industrial labor to business ownership, reflecting a capacity for adapting to various economic environments. His commitment to public welfare was evident in his advocacy for public works to combat economic depression, leading to his notable "Coxey's Army" march on Washington, D.C.

Jacob S. Coxey Sr.'s political philosophy is marked by a radical approach to economic recovery through direct action and monetary expansion. His advocacy for issuing paper money to fund public works projects reveals an unconventional belief in increasing the money supply as a solution to unemployment. Coxey's strategy of mobilizing "Coxey's Army" to march on Washington highlights a penchant for dramatic, grassroots activism. Despite his earnest commitment to the plight of the unemployed, his methods and policy suggestions often drew criticism, revealing a tension between his populist ideals and the political establishment's norms.