He was a member of the Victorian Legislative Assembly from 1914 to 1932 and from 1935 to 1950, representing the electorates of Port Fairy (1914–27) and Warrnambool (1927–32, 1935–50).
He became a law clerk at Ballarat, but enlisted to fight in the Second Boer War in South Africa as a lieutenant with the Australian Commonwealth Horse 4th Battalion during 1902; in 1903, he moved to Port Fairy and continued his former business.
[8][9] Immediately following the party's disastrous result, the state executive required Bailey to show cause why he should not be expelled, and carried out that penalty later in the year.
[10][11] Bailey applied for reinstatement at the party's January 1933 state conference, during which he pledged not to challenge an endorsed Labor candidate if rejected, but met with strong union resistance and was unsuccessful by a vote of 117–62.
He was being touted as a potential candidate for federal politics in 1948, but was badly defeated at the 1950 election, finishing third.