In 2014 James Milford became the fourth Head of School at Maclay School, a co-ed school of about 1,000 students in Tallahassee, Florida. Prior to becoming the Head at Maclay James had a long tenure at Darlington School, a day and boarding school in Rome, Georgia where he served as Head of House, as an admission officer, he led the residential program, was the Director of Student Life in the Upper School, a teacher in the Upper School, and served as Associate Headmaster overseeing admissions, financial aid and communications.

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