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The school was founded two years after the death of William Dummer, who funded it in his will. Dummer had been lieutenant governor and acting governor of Massachusetts for many years and led the colony through a difficult period in the earlier 18th Century fighting off forays by "French & Indians" during what became known as "Dummer's War" in the 1720s. He also served as an early Overseer of Harvard College.

Over the years, the school's name has been entwined with those of many famous people. Paul Revere created the first seal for the school; John Quincy Adams served as secretary to the Board of Trustees; Theophilus Parsons, a Chief Justice of Massachusetts and author of the Massachusetts Constitution of 1780, attended the Academy ; Samuel Phillips, Jr., founder of Phillips Academy, Andover graduated in 1771; Captain Edward Preble, commander of the USS Constitution and a hero of the Barbary Wars, studied there; Booker T. Washington Jr. (son of Booker T. Washington) starred on the football team in the early 1900s; Yu Gil-jun, a famous social reformer and the first Korean to study in the West, attended the school. Henry Durant, a founder of the University of California and its first president, and later an early mayor of Oakland, served as headmaster of the Dummer Academy from 1849-1852.