John de Vere, thirteenth earl of Oxford, was the last great medieval nobleman. Earl of Oxford for fifty years, subject of no fewer than six kings of England during one of the most turbulent periods of English history, de Vere's career included more changes of fortune than almost any other. His life might be used as an exemplar for the widespread medieval idea of a wheel of fortune: ‘Fortune is like a turning wheel – one moment she suddenly lifts a man up, the next she throws him down, and conversely she raises the man who is prostrate and trodden in the dust more generously than he could have hoped.’ He suffered personal tragedy as a teenager, with the execution of his father and brother, and a decade in prison in Hammes castle, yet enjoyed twenty-five years as perhaps the ‘foremost man of the kingdom’. It is this latter period after 1485 that is perhaps the most important to the historian. None of the salient features of his public career are necessarily associated with the nobility of the reign of Henry VII. Semi-independent ruler of a large region of England, whose regional position was not solely dependent on royal favour, though he maintained good relations with the first Tudor king, he possessed one of the highest incomes in England, which, though boosted by royal patronage, was based mainly on a huge private estate; equally he was a trusted military lieutenant, who put his life at risk for his king at three major battles.