Henry Tudor’s victory at Bosworth saw a change in fortune for the House of Lancaster and its supporters. Henry Clifford emerged from skulking in the shadows and in a matter of weeks was established as one of Henry VII’s great lords possibly because the good folk of Yorkshire had a soft spot for Richard III so didn’t take too kindly to the man who’d usurped his throne. As for the Earl of Northumberland, he was doing a shift in the chokey for not arriving to support Henry in time at Bosworth. Consequently there were few people for Henry Tudor to trust so Henry Clifford with his family history and the role that his brother had played on the continent was in the right place at the right time.
Clifford swiftly took on a series of administrative roles as well as touring the countryside punishing Yorkists. Eventually the role the king allotted to him became more representative of the traditional role of sheriff – administering the law and collecting taxes. It was a job that was to keep Henry out of mischief for the rest of his life along with showing his loyalty to the king every time a pretender to the crown showed his head and attacking the scots as deemed appropriate by the rules of border warfare.
In 1487 Henry got married. Anne was a distant relation of his own as well as being related to Henry VII ( a cousin of some kind) which just goes to show that medieval family trees are complicated things. Henry acquired more lands in the north, acted on behalf of the king and developed an interest in astronomy and alchemy. According to legend he was illiterate which is possible but unlikely. The one thing we can be sure of is that he valued learning. He supported scholars in Oxford and also provided places for children at Giggleswick. He also supported the monasteries at Shap, at Bolton and at Gisborough.
To all intents and purposes Henry seems to have been very pious – presumably he made confession about the number of mistresses he is supposed to have kept at various times. Lady Anne complained about the number of baseborn children he’d fathered. Gossip was ratcheted up a gear after the death of his first wife and his marriage to Lady Florence, Marchioness Pudsey who was considerably younger than him. He also seems to have conducted pretty unneighbourly warfare with his neighbour who responded in kind.
The next time wider history clapped eyes on Henry Clifford was in 1513 at the Battle of Flodden. He even made an appearance in a ballad of the same name in which he is portrayed as a heroic captain. At home things were less of a story and more of a nightmare. He was almost estranged from his son whom he kept on such short pursestrings it caused Henry VIII to tell Henry Clifford to be more generous. He also seems to have had a bit of a tempestuous relationship with his second wife Lady Florence who brought a lawsuit against her spouse for not letting her live with him. On the other hand Henry publicly accused Florence of having an affair with one of his household servants Roger Wharton – presumably Florence felt that what was good for the gander was also good for the goose! It was definitely not a happy family.
When Henry Clifford died in 1523 and was buried in Bolton Abbey the Cliffords had survived the medieval period and were rising ever further in the Tudor world but who would have thought that less than twenty years later Henry Cliffords final resting place would be dissolved along with all the other monasteries in England and Wales. Times were changing in more ways than one.