He was born in 1451 in Wollaton (Nottinghamshire), the eldest son of Robert Willoughby by his wife Margaret Griffith. His father's parents were Hugh Willoughby and his second wife Margaret Willoughby.[2]
His mother married Peter Leigh of Nottingham after his father's death. Robert inherited the Wollaton and Middleton estates from his half brother Richard in 1471. It took a further two decades for him to take full possession, since his mother Margaret Leigh had an interest in Wollaton, while his grandmother Margaret Bingham spent her life in the Middleton estate, the Dunsby and Wigtoft estates in Lincolnshire, and the manors of Gunthorpe and Lowdham in Nottinghamshire.[3]
At the origin of the Willoughby (Willuby) surname there is record of the Bugge family. 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. From them sprung the Willoughbies of Wollaton.[1]
Radulphus Bugge was an ancestor of diverse good families as observed in Willoughby-on-the-Wolds. He was a wealthy merchant and purchased the lands in 1240–41. Probably buried at St.Peter's church (Nottingham). He had two sons, Richard and Radulphus, the latter having been the father of Richard de Bingham. Richard's son, Richard de Willoughby was Knighted by King Edward II in 1325, and increased their patrimony exceedingly as a very rich lawyer.
Richard's son was Richard de Willoughby, a Justice of the Common Pleas for 28 years in the days of Edward III, who also appears to have had a few higher appointments in his career.
From his second wife, Joana (Matilda) he had a son, Sir Edmund Willoughby, who inherited the bulk of the property. In the second subsequent generation Sir Hugh married Margaret Freville and started a Barony named after the estates.
Sir Henry was their grandson and a distinguished man in his day.[1]
The Field of the Cloth of Gold, oil painting of c.1545. Henry VIII on horseback approaches at bottom left. Sir Henry could be the figure looking over the Queen, in front of what appears to be an Herald.
At the beginning of his reiving and cavalry days, Henry and his brother Richard were remained and tried for the abduction of Jane Statham. This happened after the latter become widowed at the outcome of the battle of Bosworth in 1485. The heiress of the House of York was also forcibly married to Richard and taken from her family. 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. The incident seems to have hardly affected their prosperity.
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 became a justice of the peace in Nottinghamshire from 1492 for the remainder of his life. He held the same position in Lincolnshire and Warwickshire, and served as Sheriff for all three counties.
He was buried in St Leonard's Church, Wollaton where he rests today in his canopied tomb, with effigies to all his wives.[3]
Family
He married firstly Margaret c.1470, daughter of Sir Robert Markham (d. 1490). They had the following children:
