He was elected as a councillor for Sandwell Borough Council in 1991 and was its Deputy Leader from 1997 to 2000. At the time of the resignation of Commons Speaker, Betty Boothroyd in 2000, Bailey was the Secretary of the constituency Labour Party and Deputy Leader of the local council and seemed the obvious choice to fight what was then a safe Labour seat in the impending by-election. He was chosen to fight the seat and won fairly comfortably on 23 November 2000, entering the Commons 30 years after his first attempt. He is unusual in that he has contested two Parliamentary by-elections caused by the resignation of two different Speakers of the House of Commons.