Bailey ran for the leadership of the Saskatchewan PC Party in 1973, placing second to Dick Collver.
He was elected to the Legislative Assembly of Saskatchewan in the 1975 provincial election as the Progressive Conservative Member of the Legislative Assembly for Rosetown-Elrose, and served until 1978.
He was elected to the House of Commons in 1997, representing the riding of Souris—Moose Mountain for the Reform Party of Canada and its successor, the Canadian Alliance, until 2004.
He served as the Veterans Affairs critic for the Alliance.
Bailey was also variously an educational administrator, a farmer, and a teacher.