A member of the Boston Brahmin Crowninshield family, Bradlee was born in Boston, Massachusetts, on August 26, 1921. His father was Frederick Josiah Bradlee, Jr. (1892–1970), a direct descendant of Nathan Bradley—the first American Bradley, born in the colony of Massachusetts in 1631. His mother, Josephine de Gersdorff (1896–1975), was awarded the French Legion of Honour for starting an orphanage that sheltered children from Nazi Germany during World War II. Bradlee's maternal grandfather, Carl August de Gersdorff (1865–1944), the son of a German immigrant, was a wealthy New York Lawyer. Bradlee's maternal grandmother was Helen Suzette Crowninshield (1868–1941), daughter of Artist Frederic Crowninshield (1845–1918), another member of the Crowninshield family. His great-great-uncle was U.S. Lawyer Joseph Hodges Choate, 34th U.S. ambassador to Britain, and his great uncle was Francis Welch "Frank" Crowninshield, the creator and Editor of Vanity Fair, and a roommate of Condé Nast. He had a brother named Frederick Bradlee (1919–2003), a Writer and Broadway stage actor.