Bailey was the first Christian scholar to re-evaluate the traditional understanding of the Biblical prohibitions regarding homosexuality. He was an Anglican clergyman and Canon Residentiary of Wells Cathedral. Although not a full-time academic theologian or biblical scholar, after World War II he led a small group of Anglican clergymen and physicians to study homosexuality. Their findings were published in a 1954 Report entitled The Problem of Homosexuality produced for the Church of England, and were influential in moderating the church's subsequent stance on the moral issues raised by homosexuality. The work of Bailey and his colleagues also paved the way for the progressive Wolfenden Report (1957), which was followed a decade later by the decriminalization of homosexual conduct between consenting adults in England and Wales.
As a separate project arising from this work, he undertook a separate historical study, which led to the publication of his groundbreaking book, Homosexuality and the Western Christian Tradition. Although this monograph has been criticized, it was a landmark in the history of the subject, combining scrutiny of the Biblical evidence with a survey of subsequent history. Bailey's book drew attention to a number of neglected subjects, including the intertestamental literature, the legislation of the Christian emperors, the penitentials, and the link between heresy and sodomy. Since then, his work has been overtaken by more extensive analyses by specialist biblical scholars, but it was an important influence on the early work that followed by historians (for example, John Boswell's "Christianity, Social Tolerance, and Homosexuality", and Mark D Jordan's "The Invention of Sodomy in Christian Theology ") and by biblical scholars (William Countryman's "Dirt, Greed, and Sex").
It was also important for influencing the findings of the British Wolfenden Report, which led to the decriminalisation of homosexuality in the UK, and on the later deliberations of the Anglican Church on the subject.
Bailey died in Wells in Somerset.