There is consensus among historians that Oxford held sway over East Anglia during Henry VII'S reign. Dairmaid MacCulloch argues that ‘there was no one to challenge him in his control of the region’. Christine Carpenter comments that ‘Oxford may have been given regional authority in East Anglia, and especially in Essex.’ Roger Virgoe states that ‘From 1485, John, 13th earl of Oxford, was the dominant figure in Norfolk and Suffolk, as well as in the neighbouring counties.’ Such historiographical agreement demands acceptance. Yet, given that no previous earl of Oxford had ever been the foremost magnate in the region, how did John de Vere gain such ascendancy, by what means did he maintain it, and what did his role in the region entail?

East Anglia was one of the wealthiest areas of England in the later Middle Ages. The wool trade had brought substantial prosperity to the region, and with few upland areas, it had little marginal land. Its prosperity can be seen by a comparative assessment of the wealth of English counties in 1515. Essex was, in terms of lay wealth, the third richest county, Suffolk the seventh, Hertfordshire the eighth, Norfolk the twelfth, and the small county of Cambridgeshire the twenty-first. For all its productivity and commercial prosperity East Anglia was not a place for the politically timorous in the later Middle Ages.