A 1967 graduate of St. Augustine High School, Dennis was born in St. Augustine to James A. Hollingsworth and Myrtle Moore Hollingsworth. He was the fifth of six children, all of whom were graduates of St. Augustine High School and attended Ancient City Baptist Church. His parents started, owned and operated Harley-Davidson St. Augustine for sixty-five years before they sold the franchise. The family today still owns the original property and building where they restore and race the antique vintage circuit motorcycle races. His father and brothers would hit the circuit proudly placing Harley-Davidson in the leading pack from Daytona Speedway, throughout the country.
Dennis attended Fullerwood Elementary School and Ketterlinus Junior High School. At SAHS he was class president his freshman year, band for two years, a member of the Future Teachers of America. After graduating from high school, Dennis went to St. Johns River Jr. College in Palatka graduating with his AA degree and continued his college at Florida State University. Dennis finished his Bachelor’s degree at Stetson University, returning to St. Augustine and continued working in the family business.
Dennis found great joy in serving the community teaching 9 years at St. Augustine Technical Center teaching adult education at night as while as serving the City of St. Augustine as an auxiliary policeman. Dennis attended University of North Florida for his MBA but graduated from Jacksonville University. Dennis is also an adjunct professor at Flagler College and still teaches in the public administration program.
Dennis is currently serving the citizens of St. Johns County for his tenth four-year term as an elected Florida Constitutional Officer. He was elected Tax Collector in 1984 and has not had any opposition since the first election. As Tax Collector he was instrumental in the process of having Florida tax collection agencies serve under the Department of Highway Safety and Motor Vehicle for computerization of all vessel titles & registrations and driver license issuance. He has also served as president of the Florida Tax Collectors Association and taught for the Department of Revenue for certification of Certified Florida Collector Assistance courses. Dennis is currently one of the longest continuous serving tax collectors in the State of Florida.
In the community he has served on the board of directors for the YMCA, the City of St. Augustine Police and Fireman’s Pension Trust Fund, the St. Johns County self-insured insurance plan, Learn to Read of St. Johns County, Presidio de San Agustin Commission, St. Johns County Education Foundation and the American Cancer Society. He has also been a member of Historic Kiwanis Club of St. Augustine earning the distinguished president award. In his capacity as Tax Collector for St. Johns County he currently serves as chairman of the Department of Vital Statistics for the Tax Collector’s Association, committee member for the Department of Revenue Education Committee, State Director for the National Association of Finance Directors and Tax Collectors Association, and the National Association of Counties.
As Tax Collector, he spearheaded the challenge by the Federal Bankruptcy Court to disallow local governments from the allocated interest rate on delinquent taxes after a large developer filed bankruptcy in St. Johns County. After winning the court case, Florida Tax Collectors were asked by Congress to assist in the rewrite of the Federal Bankruptcy Code in the 90’s pertaining to local governments being secured. He also worked as liaison between President George W. Bush’s administration and the local governments finance and tax collectors and comptrollers’ offices during the 2008 economic slowdown.
Dennis enjoys the opportunity to help someone each day. He has averaged earning all taxing authorities an average of 3-4 million dollars in unused or earned revenue each year which off sets his offices budget. He is the only tax collector in the State with an inter-local government agreement with the School Board to operate the driver’s education curriculum. Since he has been in office, he makes sure no one has lost their homestead property due to delinquent taxes.
The wisest and best decision of his life was when he married Jan Feltner. They are the proud parents of twin boys, Shelby and Colby.