Ruby Laffoon, born in a farming family with a political legacy, pursued a career in law and public service. After attending public schools and teaching at a young age, Laffoon studied law at Columbia Law School and Washington and Lee University. Laffoon's early career included roles as a city attorney, county attorney, and insurance executive. Laffoon served as a judge for the Fourth District Circuit Court and later as governor, during which time he organized the Honorable Order of Kentucky Colonels. Despite health challenges, Laffoon remained active in public life until his death.

Ruby Laffoon's political philosophy is marked by an intriguing blend of populist rhetoric and strategic pragmatism, as seen in his vigorous campaigning despite a physical disability. He combines religious undertones with political discourse, which adds a unique flavor to his public appearances. Laffoon's unexpected support for removing Republican officials highlights a calculated approach to governance, balancing ideological purity with practical governance needs. His creation of the Honorable Order of Kentucky Colonels demonstrates an innovative use of state symbols for political and social capital.