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.
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Bailey narrowly lost the Republican primary for a seat in the Missouri Senate in 1996, but in 2000 Bailey captured the Republican nomination for Lieutenant Governor, although he was defeated by Democrat Joe Maxwell in the general election.
Benton was director of the Missouri Department of Revenue in the administration of then-Governor John Ashcroft from 1989 to 1991, and served as an administrative aide to a United States Congressman Wendell Bailey from 1981 to 1982.
In 1992 Webster was the Republican nominee for Governor of Missouri, after defeating Roy Blunt and Wendell Bailey in the Republican Primary.
Oliver Wendell Holmes, Jr. | Oliver Wendell Holmes, Sr. | Bill Bailey | Ringling Bros. and Barnum & Bailey Circus | Oliver Wendell Holmes | Pearl Bailey | Kay Bailey Hutchison | Derek Bailey (guitarist) | Derek Bailey | Wendell Berry | Old Bailey | Wendell Phillips | Wendell Willkie | Rumpole of the Bailey | David Bailey | Bailey | F. Lee Bailey | David Bailey (photographer) | Wendell Anderson | Corinne Bailey Rae | Bailey Road | The Wendell Baker Story | Richard W. Bailey | Gary Bailey | Barnum and Bailey | Bailey Road, Patna | Bailey bridge | Wendell Downswell | Randall Bailey | John Bailey |