Henry Willoughby was the grandson of Hugh Willoughby and Margaret de Freville. Margaret outlived Hugh
Willoughby and was married for a second time to Ralph Bingham, who like her first husband was descended from Ralph Bugge. In spite of this second marriage it was
decided that her estate should pass to Henry Willoughby.
The principal home of the Willoughbys was Wollaton, but Henry reacquired the whole of the Midleton estate and frequently
hunted there.
Henry was a very powerful man. He served as Knight Banneret - which meant that he took his own men to the battlefield under
his own banner - at the battle of Stoke Field, which was a postscript to the Wars of the Roses, thus serving and becoming a
confidant of Henry Tudor.
He also served Henry VIII and was Master of
Ordnance under Thomas Grey, Marquis of Dorset on the ill-fated expedition to Gascoyne and Guyen. He married four times. A
son of his third marriage was Hugh the Explorer.