The year before the king’s death, the situation surrounding Prince Henry and Katherine’s engagement was still not reconciled with Ferdinand still reluctant to pay the remaining dowry. This financial conflict aside, England was in a reasonably comfortable place economically and this has fed into Henry VII’s image as a miser, and ‘cheap skate’, compounded by the monetary restrictions he put on Katherine of Aragon after the death of Arthur.
Towards the end of his life, Henry became more persistent in his collection of debts, perhaps becoming more focused on money after the death of his son and wife in quick succession. Two men in particular aid him in collecting payments due: Richard Empson and Edmund Dudley. These two were essentially tax collectors, but they were very good at their job.They were forceful and feared, and thoroughly disliked. As such, they were promptly gotten rid of when young Henry came to the throne in 1509, much to the pleasure of his nobles.
Henry VII became ill (not for the first time) in 1508, with what has been described as an unknown, recurrent illness though there have been suggestions that it was tuberculosis. By March of 1509, his physicians had decided that he would not recover. He passed away on 21 April, 1509. His son Henry, however, was not told until 2 days later.