Gayle's father, a pediatric intensive care specialist, who worked at the Wolfson Children's Hospital, and Gayle's mother, a nurse, who worked at the Mayo Clinic Florida, are from Jamaica and moved to Jacksonville, Florida in 1992. Gayle grew up in Jacksonville and attended high school at the Episcopal School of Jacksonville. He contributed to his high school's newspaper and interned at WJXT and The Florida Times-Union. Gayle graduated from Clemson University with a bachelor's degree in communication studies in 2010. Gayle initially planned to pursue a journalism career, but "had an itch to pursue politics" during his junior year at Clemson University. He moved to Washington, D. C. after graduating.