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Milton Academy's ten most recent Headmasters. Unfortunately, the Milton Academy archives do not include a picture of Milton's first head, Samuel Thurber
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Samuel Thurber, Principal 1885–1887
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Harrison Otis Apthorp, Principal and Headmaster 1887–1904
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Richard Cobb,
Headmaster 1904–1910
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Frank Edwin Lane, Headmaster 1910–1917
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William Lusk
Webster Field '94,
Headmaster 1917–1942
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Cyril Hamlen Jones, Headmaster 1942–1947
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Arthur Bliss Perry, Headmaster 1947–1963
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David Douglas Wicks, Headmaster 1963–1973
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Jerome A. Pieh,
Headmaster 1973–1991
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Edwin P. Fredie,
Headmaster 1991–1999
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Robin Robertson,
Head of School 1999–2007
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Theodorick B. Bland,
Head of School 2009–Present
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