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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—Laurent A. Daloz (20th century)
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—Barbara Tuchman (1912–1989)