Career
Bailey was a lawyer who represented timber and railroad companies before he was elected judge, then a part-time position. He presided over the trials of the coal miners involved in the Battle of Matewan, the events of which are depicted in the movie Matewan. His diaries and notes formed the basis for the movie script.
In 1944 and 1952, he ran for governor but lost the primary election on both occasions.
He died in 1963. Rural Delivery Bailey Lake is named for him.