In the summer of 2014, James Milford became the fourth Head of School at Maclay School, a coeducational college preparatory day school enrolling nearly 1,000 students in Tallahassee, Florida. He brought broad experience in all aspects of independent schools as a teacher, parent, and administrator. Before joining Maclay School, Mr. Milford had a long tenure at Darlington School, a day and boarding school in Rome, Georgia. He joined Darlington as a Head of House and Admission Officer. During his time at Darlington, 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. 

Mr. Milford has served for four years on the Florida Council of Independent Schools (FCIS) Board.  He is the Chair of the Finance committee and an Executive Officer of the Board.  In his words, “My mentors are the only reason I am here today, and I will spend the rest of my career paying that kindness and generosity back to those I am able to invest in.”  He does this through his involvement in FCIS, serving as a faculty member for the past four years for the FCIS Prospective Heads Institute as well as the FCIS New Heads Institute and is a frequent presenter at FCIS conventions.  Milford serves on the Commission for Accreditation and leads both FCIS and Southern Association of Independent Schools (SAIS) Accreditations across the Southeast. 

Mr. Milford has worked in numerous areas of independent school life, including admission, retention, and communications, expanding the scope and reach of how the school connects and partners with parents. His work focuses on the cultural stability and the resulting health of the school and his passion revolves around empowering faculty, staff, and students to reach their highest potential. He states, "Good people want to get better, and it is my goal to make sure the culture of the school supports this for all members of the school community--faculty, staff, parents, and students." 

Mr. Milford received his Master's in Business Administration with a concentration in Entrepreneurship from the Campbell School of Business at Berry College and his Bachelor's of Business Administration with a concentration in Accounting from Shorter University.   

He and his wife Angie, Maclay's Cross Country and Track & Field Coach who led the girls track to a state championship in 2023, have three sons: Clayburn (graduate of West Point), Kennan (Maclay '21) and James David (Maclay '23).  The Milford family lives in Northeast Tallahassee and spends their free time training, racing, making memories with the boys, and entertaining friends. Though you may find Mr. Milford in his office or around campus, it is not uncommon to see him leading cheers at pep rallies, on the Junior Ski Trip and Sophomore Safari, or wearing one of his many "colorful" suits.  Be sure to follow the hashtag #manyfacesofmrmilford on Instagram!