He graduated from Harvard College with a Bachelor of Arts in ancient Greek history and literature.
He then received a BA and MA from the University of Oxford in English language and literature.
[1] Ragle began his career in education teaching English at Exeter Academy.
[4][5] From 1981 to 1983, Ragle was a visiting fellow and administrative assistant to the president at the University of Vermont.
He then was a visiting fellow and administrative assistant to the president of Trinity College in Burlington, Vermont.