He received his BA degree in 1938 from Rice University, after which he attended law school at the University of Texas and then the Virginia Theological Seminary, obtaining his Master in Divinity degree in 1942.

He married Evelyn Louise Williams in 1943 and entered the navy as a chaplain that same year, serving in the South Pacific Theater.

He was called to serve as rector of All Saints' Church in Austin in 1951[2] and Director of Episcopal Student Activities at the University of Texas.

In 1961, Bailey was designated canon to the ordinary and moved to the diocesan headquarters in Houston.

[4] He served there until 1975 when he was named on the sixth ballot as bishop coadjutor for the Episcopal Diocese of West Texas on September 3, 1975, during a special council meeting which took place in Christ Church in San Antonio, Texas.