Bennett was educated at the Royal Grammar School, Guildford, Southend High School for Boys and the University of Cambridge. He became an ordained priest, a published historian, a Fellow in Modern History at New College, Oxford and College chaplain, a Canon of Chichester Cathedral and a member of the Church of England General Synod and its powerful standing committee. He was a well known figure in ecclesiastical politics in England, latterly rather definedly on the conservative wing of the Anglo-Catholic movement, being a noted figure in the opposition to the ordination of women.
Crockford's Clerical Directory is a "who's who" of the Church of England, published annually by the Church itself and containing brief biographical details of every cleric in Britain and Ireland. It was traditional for the preface to the Directory to be written anonymously and to take a slightly waspish, if detached and amused, look at events in the Church over the past year. Bennett was asked to pen the preface for the 1988 edition of the Directory, which was published on December 3, 1987.
Bennett consciously took a different tack on the article and wrote a carefully constructed demolition of the hierarchy of the church of England from a conservative viewpoint, which he himself described as "wicked". In it Bennett excoriated what he perceived as an intolerant liberal elite in the Church of England, headed by then Archbishop of Canterbury Robert Runcie, a process which he felt would follow a trail already blazed by the Episcopal Church of the United States of America and would lead inexorably to a steep decline in the fortunes of the Church. Specifically, he argued that Runcie was guilty of cronyism, appointing only those to high office who he had known through Westcott House or Ripon College Cuddesdon theological colleges or else the Dioceses of Canterbury and St. Alban’s.
While the explosive nature of the article in ecclesiastical circles might well have been predicted, it was more surprising that the secular press turned the issue into front page news. After a number of days of fevered speculation, it emerged that Bennett was the anonymous author and the last entries in his diary make clear that he was finding the attentions of the tabloid press increasingly difficult to cope with.
On December 7, Bennett killed himself. His death and the events which led up to it continue to divide those who take an interest in church matters. Conservative Anglo-Catholics and many others opposed to the ordination of women view Bennett as a martyr, hounded to his death by the machinations of the Church of England spin machine for saying something that everyone knew to be true. Liberals and moderates, while agreeing that his death was a tragedy, point to the fact that Bennett was not without his problems – a lonely man who never came to terms with a homosexuality that was obvious to most, who had recently lost a mother to whom he was particularly close and who was bitter at his lack of advancement under Robert Runcie, who had been a personal friend.