After legal training and before he came into his inheritance, he represented Nottinghamshire in the Parliament of February 1324. Later that year he was appointed a serjeant-at-law, becoming in 1328 a Justice of the Common Pleas and in 1330 was promoted to the Court of the King's Bench. In 1332, while serving on a judicial commission in the East Midlands, he was kidnapped by the infamous Folville gang and their Coterel allies, who wanted 1300 marks for his release. Willoughby was notoriously corrupt—the royal yearbooks would later report Willoughby as selling the laws of the land "as if they were cattle or oxen"—and according to the near-contemporary Knighton's Chronicon, the Coterel associates had much to feel aggrieved about. He was able to raise the money and was compensated by the government with an annual payment of 100 marks. On three occasions he served briefly as Lord Chief Justice during the absence of Geoffrey Scrope. Controversy again surrounded him when on judicial business in 1340 he was besieged for two days at Thurcaston in Leicestershire by another criminal gang. Later that year, as part of King Edward III's purge of the administration, he was demoted to puisne rank, transferred back to the lower court of common pleas and then imprisoned in Corfe Castle in Dorset on charges of corruption. On trial the next year he eventually pleaded guilty and paid a 1200 mark fine, followed by a humiliating circuit round the county courts to answer any local accusations. Whatever faults caused his downfall, he seemed to be forgiven by 1343 when he was reappointed to the common pleas bench, where he served until his retirement in 1357. In parallel with his judicial career, he actively added to the not inadequate lands his father had left him, primarily in his native Nottinghamshire. In addition, he benefited from lands brought to him in his three marriages, particularly the last. By his death he had increased his annual income in rents, coming out of nineteen counties, from about 140 pounds in 1325 to over 500 pounds, a massive amount at the time. He died on 14 March 1362 and was buried in the church of Willoughby on the Wolds in Nottinghamshire, where his monument can still be seen.
Family
In 1310, when he was about 20, he married his first wife Isabel, daughter of Sir Roger Mortein, of Dunsby in Lincolnshire, and his wife Isabel, daughter of William Touchet. After her death, in 1333 he married Joan, widow of Sir Bertram Monboucher and daughter and sole heiress of Sir Guiscard Charron, of Beamish in County Durham. His third wife was Elizabeth, widow of Sir Richard Champernowne, of Modbury in Devon. His daughter and heiress was Lucy, who married first Sir Thomas Huscarle, of Purley Magna in Berkshire, and secondly Nicholas Carew, of Beddington in Surrey.
