He was born in 1451 in Wollaton (Nottinghamshire), the eldest son of Robert Willoughby by his wife Margaret Griffith.

They were either the original inhabitants of the town of Wollaton, or settled in it about the time of King John, rising to considerable eminence.

In the second subsequent generation Sir Hugh married Margaret Freville and started a Barony named after the estates.

[3] At the beginning of his reiving and cavalry days, Henry and his brother Richard were remained and tried for the abduction of Jane Statham.

As a consequence, the Willoughbys had to pay large sums in compensation to the victim and affected family members, the marriage having also been annulled.

He was Master-General of the Ordnance to Henry VIII in 1512 and raised a retinue of more than 800 men to campaign in Spain, during the conquest of Iberian Navarre.

He had much influence in the Midlands thanks to his great wealth, based mostly on coal from the Wollaton pits, which he exploited with fresh vigour.

He was buried in St Leonard's Church, Wollaton where he rests today in his canopied tomb, with effigies to all his wives.