Heads of School and Foundation
- Headmistresses of Rosemary Hall: Caroline Ruutz-Rees 1890–1938; Eugenia Baker Jessup '10, 1938–53, 1957–58; Helen MacKissick Williamson 1953–57; Alice McBee 1958–71; Elizabeth Winslow Loomis 1971–73.
- Headmasters of The Choate School: Mark Pitman 1896–1905; Sumner Blakemore 1906–08; George C. St. John 1908–47; Seymour St. John '31, 1947–73.
- Headmasters of Choate Rosemary Hall: Charles F. Dey 1973–91 (initially president and principal of The Choate School and Rosemary Hall); Edward J. Shanahan 1991-2011; Dr. Alex Curtis 2011-.
- Presidents of The Choate School Foundation: George C. St. John 1911–47 (The Choate School, Incorporated 1911–37; The Choate School Chapel Foundation 1924–29; The Choate School Chapel and Library Foundation 1929–37; The Choate School Foundation 1937–47); Richard R. Higgins 1947–58; Donald McK. Blodget '13, 1958–61; Craig D. Munson '16, 1961–66; Daniel G. Tenney, Jr. '31, 1967–74.
- Presidents of Rosemary Hall Foundation: Caroline Ruutz-Rees 1890–1938 (headmistress and owner); Catherine B. Blanke '25, 1950–55; Franklin E. Parker, Jr. 1950–54 (chair); Elizabeth B. MacDonald '21, 1956–60; H. Chandler Turner, Jr. 1960–62; Julian M. Avery 1962–65; Gerrish H. Milliken 1965–74.
- Chairs of Choate Rosemary Hall Foundation: Elizabeth Hyde Brownell '21, 1974–77; Peter C. Goldmark, Jr. '58, 1977–79; Larry A. Hart '32, 1979–82; Bruce S. Gelb '45, 1982–85; William G. Spears '56, 1985–90; Stephen J. Schulte '56, 1990–95; Edwin A. Goodman '58, 1995–2000; Cary L. Neiman '64, 2000–05; Herbert V. Kohler, Jr. '57, 2005–10; Michael J. Carr '76, 2010–present.
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—Margaret Mitchell (1900–1949)
“In a large university, there are as many deans and executive heads as there are schools and departments. Their relations to one another are intricate and periodic; in fact, “galaxy” is too loose a term: it is a planetarium of deans with the President of the University as a central sun. One can see eclipses, inner systems, and oppositions.”
—Jacques Barzun (b. 1907)
“True it is that she who escapeth safe and unpolluted from out the school of freedom, giveth more confidence of herself than she who cometh sound out of the school of severity and restraint.”
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—John Locke (1632–1704)