Many myths and assumptions have been woven around his privations in prison as a supporter of the Tudor party's opposition to Richard III in the years 1483–85, and are still to be found recounted as facts.

The Wyatt family papers in the British Library[1] contain material which provides the nearest that can be found to an authentic account of this period of his life.

The aim was to play up the glory days of Henry's adherence to the Tudor cause, describing him inter alia as "his Country's martyr".

He appears to have had contacts among those close to the Scots king James III and may have been an intermediary in attempts to secure Scottish support for Henry Tudor's invasion.

Possibly he fell into the hands of "some Scottish baron with Yorkist sympathies, only to be released when Henry VII was securely on the throne, after a considerable period of cruel imprisonment, and on the promise of a huge ransom.

His possibly apocryphal exploits in the Wyatt family papers included being "imprisoned often, once in a cold and narrow Tower", where he would have starved but for the ministrations of a kindly cat who befriended him and brought him food.

[2] The myth and claim that he was imprisoned in the Tower of London finds its first appearance in 1702 on a stone tablet in Boxley church erected by Edwin Wyatt, Henry's great-great-great-grandson.

His close connections with Scotland came to the fore in his later career as Henry VII's agent in that country,[9] for which there is ample evidence of his employment on secret and sensitive missions.

In 1511 he was made, jointly with Sir Thomas Boleyn, constable of Norwich Castle and on 29 July of the same year granted the estate of Maidencote, in Berkshire.

With a contingent of some 100 men he took part in the king's campaign in France in 1513, and was made knight banneret after the Battle of the Spurs, where he had served in the vanguard.