Willoughby’s great-grandfather, Sir Thomas Willoughby, was a younger son of Christopher, 10th Lord Willoughby of Eresby. The family had held land in Lincolnshire since the end of the twelfth century and represented the county in 1325 before being raised to the peerage. Sir Thomas Willoughby was chief justice of the Common Pleas from 1537 to 1545 and acquired Bore Place in Kent by marriage. His son Robert married the daughter of Sir Edward Willoughby of Wollaton, three miles west of Nottingham.
Willoughby himself married the eldest of the six daughters of Sir Francis Willoughby, Sir Edward’s grandson. As Sir Francis had no sons, Willoughby was recognized as heir-presumptive, and on returning from his travels abroad in 1582 he settled at his father-in-law’s subsidiary seat at Middleton, five miles from Tamworth. However Sir Francis had spent lavishly on the rebuilding of Wollaton Hall, running up substantial debts,
Willoughby’s father-in-law died in the same year as his father and, despite substantial land sales, the liabilities on the estate totalled over £35,000, whereas the net income was less than £600. In addition, after her husband’s death Lady Willoughby reputedly gained possession of £8,000 worth of plate, jewels and cash belonging to Sir Francis. There was subsequently prolonged litigation between Willoughby and his wife’s step-mother, who remarried the 3rd Lord Wharton, which can only have further undermined his finances.
Willoughby was knighted at Worksop as James I journeyed south to take up possession of his new kingdom, and two months later he entertained Anne of Denmark and the royal children at Wollaton.
By November 1606 Willoughby was in the Fleet for debt.
a man after my own heart, sweetly natured, sure of word and deed, delightsome in conversation, respective of his friend, loving and faithful to his worthy lady, zealously careful of his son’s good, every way and generally learned, wise, and well experienced.
Ridgeway, treasurer of Ireland, obtained for him the grant of 6,000 acres in Ulster, which Willoughby sold a few years later.
There is no evidence that Willoughby sought re-election for Nottinghamshire in 1614, but he was again returned at Tamworth. He left no trace on the records of the Addled Parliament, but may have used the occasion to improve his acquaintanceship with Sir Robert Mansell*, who sat for Carmarthenshire and was granted the glass monopoly in the following year. Willoughby contracted to set up an experimental glassworks at Wollaton, supplying all the fuel and most of the raw materials; but hopes of vast profits proved illusory, and it closed down after a couple of years.
Willoughby was outlawed for debt in London on 29 Apr. 1622, and again in 1623 and 1624.
