Gayle was born in Jamaica to parents who both worked in medicine. After the family moved to Jacksonville, Florida in 1992, his mother worked as a nurse at the Mayo Clinic Florida and his father, a pediatric intensive care specialist, worked at the Wolfson Children's Hospital. 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. He also was a member of the cross-country and track teams, and won state championships as a member of the 2003 cross-country and 2005 4x800 relay teams.