On the 18th of May, 1756, Dr Gregory succeeded Dr Conybeare as Dean of Christ Church. He was in appearance, as in charm and dignity of manner, well suited for such an office. Kind, courtly and genial, it was his pleasure as well as his duty to attend the functions of the university, and in his day he was unsurpassed in Oxford society. He was not very learned, but he was a man of the world, and the Earl of Shelburne, who thought it worth while to write some memories of the sleepy Oxford, in which Dean Gregory took so important a part, describes the dean as the kind soul that he was. ‘Dr Gregory succeeded Dr Conybeare and was very kind to me, conversed familiarly and frequently with me, had kept good company, was a gentleman though not a scholar, and gave me notions of people and things, which were afterwards useful to me.’ Such a characterisation might have astonished the dean himself, who would have regretted with mild wrath his kindness to this young malapert, and would no doubt also have gone for the assurance of his learning to those Latin hexameters, which he as a self-made laureate had written at moments of public interest. One set was upon the death of George I. and the accession of George II., while another poem touched on the death of George II. and the accession of his grandson; they were both considered very scholarly, but, at the best, Oxford in Dean Gregory’s days was not so very learned. Of all the heads of colleges, who are put into the guide book to Oxford, used by the tourists of 1760, there is not one, whose name is familiar, unless we count that of Dean Gregory, who also might have passed into oblivion had it not been for his greater father.