Henry was the single child of Patrick Henry Hughes and Ann Margaret Doherty Hughes, raised in the Hilton area of Newport News. He graduated from St. Vincent High School (now Peninsula Catholic High School). He was a proud veteran, having served 6 years in the Airforce during the mid 60's. While stationed at Torrejon Air Force Base, Madrid, Spain, Henry played baseball and was an accomplished pitcher. Upon discharge from the Airforce, Henry studied at Christopher Newport College and went on to receive his MBA from Old Dominion University. Henry taught briefly as an adjunct professor of Economics at Christopher Newport College and also worked as a broker at Wheat First Securities.
A lifelong resident of Newport News, Henry was an avid golfer and an amateur writer of poems and short tales. He enjoyed dining out, playing cards and socializing with friends.