Cyril Norwood, to all appearances, was the quintessential insider of English education in the first half of the 20th century. An outstanding classical scholar, Oxford educated, a successful headmaster before returning to Oxford as president of his college, St John's, knighted for his services to education in 1938, he was also prominent in national education policy well before his career culminated in 1943 in the Norwood Report on the secondary school curriculum and examinations. Yet he was also an outsider, insecure because of the circumstances of his childhood and upbringing, never fully accepted in the public schools over which he presided, not fully trusted by the officials at the Board of Education or by many of his colleagues despite his decades of public service. This study investigates the paradoxical nature of Norwood's contribution to and significance in English education, a victim of social class anxieties and insecurities even at the same time that he became the most famous celebrant of the so-called "English tradition" of education.