Born in Wellsboro, Pennsylvania, Bailey received an A.B. from Lafayette College in Pennsylvania in 1880, and was admitted to the Colorado Bar in 1882. Bailey married Lutie Wilkin in Denver in September 1888.[2] He was a judge of the Eleventh Judicial District of Colorado from 1892 to 1908.[2] Following Bailey's death, Governor Oliver Henry Shoup appointed former justice John C. Campbell to the seat.[3] The Fox News political commentator Jesse Watters is a descendant through his mother, Bailey's great-granddaughter, Anne Purvis Bailey.[4][5][6]