Chaplain Bailey earned the Master of Divinity degree from the Regent University. He is ordained and endorsed to serve as a chaplain by the Spirit-Filled-Coalition of Chaplains. He completed Clinical Pastoral Education at the Memphis VA Hospital in Memphis, TN and the Methodist LeBonheur Hospital. Chaplain Bailey is a Board Certified Chaplain with the National Association of Veterans Affairs Chaplains. Chaplain Bailey serves as the Wing Chaplain for the 187 Fighter Wing in Montgomery, Alabama, where he provides leadership for two officers and three enlisted airmen. Chaplain Bailey has served over 30 years to include the following combat tours; Operation Iraqi Freedom (2009), Operation Enduring Freedom (2012), and Operation Inherent Resolve (2018)