Bailey was probably from an Oxford family,
Two years later, Bailey became mayor of Oxford for the first time. He must have enjoyed the respect of his fellow burgesses, since he served three consecutive terms in the office and was re-elected to a fourth shortly before his death. Late in his first term, he and the Oxford university authorities confronted a serious outbreak of disorder, for on 29 Aug. 1441 rioting broke out between northern and southern members of the university. In spite of the efforts of the university’s chancellor William Gray, assisted by Bailey, to restore order, the disturbances extended into the following day.
