A Graduate Once... An Alumni Forever

Douglass F. Wiles

A 1970 graduate of St Augustine High School, Doug Wiles is President of Herbie Wiles Insurance. Doug has served in the U.S. Army (1975-1980) achieving rank of 2nd Lieutenant as well as served in the Florida National Guard (1980-2000) achieving the rank of Lieutenant Colonel.

Doug was born in Andalusia, Alabama while his parents Herbert (Herbie) and Annette Wiles were students at Florida State University.  When his father had an opportunity to work in broadcasting at a small radio station the family moved to DeFuniak Springs in 1958.  However family returned to St. Augustine in 1961, when his father opened his own agency, Herbie Wiles Insurance.

In his early years, Doug attended Fullerwood Elementary School, where he learned to play trumpet, and Ketterlinus Junior High School.  At SAHS, he was in the band his first two years and then tried out for the football team.  Doug joined the Key Club and was selected for Boy’s State between his junior and senior year.  By the time he was a senior, Doug caught the eye of his English teacher, John Mantalas, who recommended him for a debate scholarship at St. Johns River Junior College. During training in the Army ROTC he earned a scholarship at the University of Florida and where he met his later wife Doris (Klein).

During his time in high school and college, Doug lived his dream as he worked as an announcer at WFOY.  In 1975 Doug graduate as a Distinguished Military Graduate of the University of Florida (UF) with a Bachelor of Science Degree in Journalism. Within 6 months of graduation, he and Doris were married, then were off to West Germany for a 3-year tour along the iron curtain along the East German Border where he served as platoon leader, executive officer, and public affairs officer in the 11th Armored Cavalry Regiment.  On January 1, 1979, a new career in insurance began when he joined his father at Herbie Wiles Insurance.  As a member of the Florida Army National Guard, he was selected to command Troop E, 153rd Armored Cavalry.  Doug was ordered to state active duty 16 times during his 25 years in uniform, responding to hurricanes, humanitarian efforts, riots, and providing assistance to law enforcement.

Doug has served on several insurance company agent advisory councils and earning two professional designations – Accredited Advisor in Insurance and Chartered Property as well as Casualty Underwriter.  His is a member of the Florida Association of Insurance Agents and served as chairman from 2017 to 2018.  Doug was elected to the Florida House of Representatives in 1996 and reelected three times until term-limited in 2004, representing four counties and more than 130,000 residents in Northeast Florida. He served as House Minority Leader and served on key committees during his final term, 2002-2004.

Doug is very active in the community in various organizations such as serving as the Kiwanis Club of Historic St. Augustine, the YMCA, SA/KHS Alumni Association and member/elder of Memorial Presbyterian Church.  Doug has also served as a trustee for Flagler Hospital, University of Florida Historic St. Augustine, Inc. and UF Whitney Laboratory for Marine Bioscience.

Doug has two daughters Lindsay and Ashley as well as 6 grandchildren whom you will find Doug and Doris enjoying their family time by walking, playing games and heading up picnics.