Bailey is a Tidewater, Virginia native and graduate of Washington & Lee University, George Washington University, and Honor Graduate and Thesis with Honors from Southwestern Graduate School of Banking at Southern Methodist University.  He also graduated with honors from the Virginia Bankers Association School or Bank Management. 

He is married to Susan Heflin Bailey, they have one daughter, and the family resides in King George County.  As an active member of the community, Bailey participates in many volunteer activities.  He served on the Monte Carlo Committee for the Germanna Community College Education Foundation, was a speaker for the United Way and served as Chairman of the Board for the Children's Home Society of Virginia, a statewide agency involved in pregnancy counseling, foster care and adoption services, and as the President of the King George Chamber of Commerce.  He and Mrs. Bailey are historical interpreters, leading a youth group which has donated over 3,500 hours to George Washington's Fredericksburg Foundation in each of the last three years.  Mr. Bailey is pictured to above with one of his many character costumes.