He graduated from Southwest Missouri State University, where he was a member of Tau Kappa Epsilon fraternity, with a degree in Business Administration and owned an automobile dealership in Willow Springs.

[6] After serving as mayor of his native Willow Springs, Bailey was elected to the Missouri House of Representatives in 1972 and re-elected in 1974, 1976, and 1978.

In 1992 Bailey made an unsuccessful bid for Governor of Missouri, finishing third in the Republican primary behind then-Attorney General William L. Webster (who won the nomination) and then-Secretary of State Roy Blunt.

Bailey cast himself as the only pro-choice candidate in the 1992 GOP governor's primary, whereas Webster and Blunt were both clearly anti-abortion.

In 2006, the St. Louis Post-Dispatch reported that Bailey was working in the Kansas City, Missouri office of the Small Business Administration as a regional advocate representing Missouri and neighboring states Iowa, Kansas, and Nebraska.