Holly Hill Academy hires former Chapin school as head of school

By Thomas Grant Jr.

Former Chapin head football coach Justin Gentry has a new job title at a different school.

On Tuesday, he was introduced as the new head of school at his alma mater Holly Hill Academy starting this fall. He and his family most recently moved to Eutawville.

Located in Orangeburg County, Gentry graduated in 1990 where he played in four different sports (football, basketball, baseball, and track).

“Some of my fondest memories were growing up here and attending HHA for all 12 years of my schooling,” Gentry said in the announcement. “I met lifelong friends, and I had tremendous teachers who dedicated their hearts and souls to helping me become the person I am today.”

A graduate of Francis Marion University, Gentry has 28 years of teaching experience in third, sixth, seventh and eighth grade language arts and reading.

He also spent over three decades coaching athletics. Gentry won 146 games with stints at Williston-Elko and Lake City before retiring last year as the second longest tenured coach at Chapin.

In 2022, Gentry served as South head coach at the Touchstone Energy Cooperatives All-Star Game in Myrtle Beach.

Along with the victories, Gentry guided the football team through three classifications. He also oversaw numerous players into the college ranks, most recently his son Thornton.

Photo by Edward Walker