Born in Old Town, Maine on April 5, 1874, the son of a prominent Maine lawyer who served in the Maine Legislature in 1870, Taber Davis Bailey graduated from Bangor High School in 1892 and Bowdoin College in 1896.
After leaving Bowdoin he studied law in the firm of Davis & Bailey, the former partner being ex-Governor, Daniel F. Davis.
In August, 1898 he was admitted to the bar and by age thirty-five had established a large law practice as well as extensive interests in Maine timberlands.
A member of the Bangor City Council from 1897 to 1900 he was President of the Common Council in 1901. From 1902 to 1903 he was City Solicitor for Bangor and in 1913 he was elected to the Maine State Senate.
Reelected in 1915 and 1917 he served as President of the Maine Senate in 1917 and 1918.