Whitefield, a cloth merchant by trade, was one of the 25 men of Hereford nominated by the Crown on 20 July 1377 to act as keepers of the city, with full powers to array the inhabitants, and it was in the following year that he was first chosen to represent Hereford in Parliament. From then onwards for some 25 years he was frequently required to witness local deeds. That he stood high in the estimation of his fellow citizens is indicated by his being selected, in the winter of 1383, as Hereford’s first mayor ever, and by his re-appointment for two consecutive annual terms during the last decade of the century.
In June 1404 Whitefield was recorded in possession of property near the north gate of Hereford, but the whereabouts of his other holdings has not been discovered. Some three years later he attested the parliamentary election indenture at the guildhall, but nothing is heard of him thereafter.
