Gary is a multi-generational native Floridian, originally from Lynn Haven, and a resident of Mount Dora since 1984.

Gary and his wife of 39 years, Carla Pepperman, have three children: Tyler, a Marine Corps officer, paramedic, and resident of Charleston, South Carolina; Jourdan, a medical doctor specializing in obstetrics and gynecology, and resident of Pittsburgh, Pennsylvania; and, Madison, a Florida attorney, residing temporarily in San Antonio, Texas. They also have four grandchildren.

Gary has been a practicing attorney since 1986, having earned his Juris Doctorate from the University of Florida. He also holds a degree in accounting having earned a Bachelor of Business Administration from Stetson University.