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Called from St. Mark's, where he had been Senior Master, after a brief faculty-led interim by Pomfret's Mr. Boulton in the weeks following Peck's death. Peck reportedly consulted the older boys before naming his successor and chose Olmsted to continue the founding work. Olmsted formalized the school's name as "Pomfret School" in 1899. Under his thirty-two-year tenure, architect Ernest Flagg designed a campus master plan (1905) and the school grew to include Clark Memorial Chapel, a gymnasium, dormitories, and other facilities. He died on December 10, 1929, after a brief illness.

Born April 4, 1894 in New York City to Louis E. and Hellan Gibson Lefferts, Lefferts graduated Yale's Sheffield Scientific School in 1914 in engineering. His WWI service as a Captain of Artillery — where he tutored a "group of his command" — pivoted him from engineering to education; he returned to Yale for a graduate degree in education and joined the Thacher School (Ojai, California), eventually serving as Assistant Headmaster. Selected by Pomfret's Board on March 5, 1930, Lefferts was at thirty-five the youngest Pomfret headmaster to that date. On the opening day of his first term he ended the dormitory segregation of new boys and added biology, chemistry, and drawing to the curriculum. He led Pomfret through the depression-era enrollment trough (~87 students in spring 1934), founded the Faculty Adviser program (1935-36), authorized the school's first paid alumni-and-development position in 1934 (its first holder was future successor Dexter Strong), and shepherded the community through the Great New England Hurricane of September 21, 1938. He resigned in 1942 to enlist in the U.S. Army's Morale and Education Division. After Pomfret he served as headmaster of Sewickley Academy in Pennsylvania. He died on October 16, 1979.

A Portland, Oregon native, Strong graduated Phi Beta Kappa from Williams College and joined the Thacher School (California) faculty under his future predecessor Hal Lefferts. Strong then arrived at Pomfret a full decade before assuming the headmastership: Lefferts had recruited him to the Pomfret faculty in 1932 as a lower-form teacher, and from 1934 he served as Pomfret's first paid alumni-and-development officer — the foundation of the modern Development Office. Lefferts then promoted Strong to Assistant Headmaster in 1941 — a small additional stipend, but the position that placed him directly in line for the headmastership the following year. Theodore "Tad" Sizer '49 (later Dean of the Harvard Graduate School of Education) described him as "the antithesis of 1940s independent Episcopal boarding school traditions — more humane, less concerned about appearances." Under his nine-year tenure as Headmaster, the Board adopted a regional scholarship plan with the explicit mission to "broaden the geographical base"; by 1948 enrollment peaked at 151 students drawn from 11 states, DC, one U.S. territory, and four foreign countries. After Pomfret, he led Lakeside School in Seattle, Washington. He died in 1985.

A New Yorker who earned his A.B. (high honors) and Ph.D. in economics at Harvard and taught there as Assistant Professor of Economics before being recruited to Pomfret. Deitch arrived to lead the school through a near-existential financial crisis: enrollment had been declining since the early 1960s and Pomfret carried roughly $500,000 in operating deficits. He launched an emergency fundraising drive — anchored by trustee Henry "Hank" Strong '41's $450,000 pledge in 1975 — that bought the school time to survive. He also oversaw Pomfret's first official institutional financial aid package (1975), broadening accessibility. Faculty resistance to his curriculum reforms led to his resignation in April 1976.

Launched the "Promise to Posterity" capital campaign in 1977, a $2.5 million effort to eliminate debts and grow the endowment. The campaign helped stabilize the institution after the school's worst financial crisis in eight decades.

A Yale graduate (B.A. American Studies 1961, M.A.T. 1965) and former English teacher at Iolani School in Honolulu — where he was deputy to his future Pomfret predecessor Burton MacLean — Keator came to Pomfret from Chestnut Hill Academy in Philadelphia, where he had been headmaster since 1972. His grandfather Austin Roche '24 had graduated from Pomfret during Olmsted's tenure, and his three sons all graduated during his own (Classes of '82, '84, and '89). Under Keator, Pomfret launched the Schwartz Visiting Fellows program in 1988, with Shirley Chisholm as its first fellow, and completed The Campaign for Pomfret, which raised $4.75 million toward the endowment recovery begun under Deitch.

A Williams College graduate (1969) who came to Pomfret from Woodberry Forest School in Virginia, Bassett completed a Kellogg National Fellowship studying gender equity in education before his appointment. He named coeducational leadership his explicit mission — "to become a leader in the coeducational world" — and commissioned the 1989-90 "T-Study," a year-long internal review of how Pomfret was serving its female students. Acting on the findings, he appointed Stoney Reed Leonard as the school's first Dean of Women, authorized a campus chapter of the Council for Women in Independent Schools (co-chaired by Margie Hueppl and Caroline Twomey), launched the 1991-92 Multicultural Awareness Program under the theme "Unity amidst diversity," and recruited Michael Gary '82 to return as Director of Multicultural Affairs. After Pomfret he served as president of the Independent Schools Association of the Central States (ISACS) and later of the National Association of Independent Schools (NAIS).

Born July 1, 1950 in Concord, Massachusetts, and a Pomfret graduate himself (Class of 1968), Hastings was named on December 12, 1992 to succeed Bassett, taking office July 1, 1993. As a young teacher he coached the earliest girls' ice hockey team (1973) and presented the first Pomfret Bowl to a female recipient, Jessica Birdsall '77. As Headmaster he oversaw the school's 1994 centenary, expanded the DEI infrastructure begun under Bassett — including the 1995 hire of Michael Gary '82 as Director of Multicultural Affairs — and dramatically expanded international programs and financial aid across his eighteen-year tenure.