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

Gary is married to Carla Pepperman, a Lake County judge, with whom he has three children, Tyler, a Marine Corps Captain and paramedic, Jourdan, a medical doctor specializing in obstetrics and gynecology and who is the mother of his two grandsons, and Madison, a Florida lawyer who is the mother of his two granddaughters.

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.

Before becoming clerk in 2018, Gary was the Chief Deputy Clerk in Lake County for seven years. Prior to that, Gary spent the majority of his career as a municipal attorney.