Bailey was first elected to the Bangor City Council at the age of 23 in 1897. He served on the City Council until 1900. A year later, he was elected President of the Bangor Common Council. In 1902 and 1903, Bailey served as Bangor City Solicitor. In 1912, Bailey was elected to his first term in the Maine Senate. He left the Senate again until his election in 1916, after which he was chosen as President of the Maine Senate by his colleagues. In 1919, he launched an unsuccessful bid for the office of Governor of Maine. He was again elected to the Senate in 1922, to his third and ultimately final term.
