He is currently a member of the Canadian Alliance in the Canadian House of Commons, representing the riding of Souris--Moose Mountain since 1997 (He was a member of the Reform Party of Canada until 2000). Bailey has been an educational administrator, a farmer, and a teacher. Bailey is the Veterans Affairs critic for the Alliance.
Other political experience Bailey was a trustee in Borderland, Saskatchewan from 1984 to 1993, and was a Progressive Conservative Party of Saskatchewan member of the Legislative Assembly from 1975 to 1978.