He had a famous name but it is not clear whether he was related to the Digby Willoughby (1769 – 1856) who was 7th Baron Middleton. His father was Richard Willoughby, and he was born in London in 1853. He came to Hull and married Clara Kellington in 1875. It was later said that he was a tailor who had served his apprenticeship in Jermyn St, London, but by 1881 he was a perfumer employing three people at the Golden Cup, 64 Brook St, Hull. He then switched to selling toys and fancy goods and in 1891 the family lived at 44 Prospect St.
He became a Conservative member of the City Council in 1914, was Sheriff in 1919 and Lord Mayor in 1924/25. He was a member of every council committee going and Chair of several, including the Tramways Committee. When the General Strike came in 1926 he thought that he alone could save Hull from the red revolution which he believed was imminent. He interfered with the management of the tram workers, and came to blows with the manager, Rayner, in the Guildhall. The Council congratulated him on his heroic performance as supremo during the emergency, but the people hated him and for six months he needed police protection. He lost his council seat, but was so highly regarded by his party that a vacancy was immediately created for him. He caused a storm when he chaired a committee entrusted with the arrangements for the Banqueting Chamber in the Guildhall. He commissioned a large, stained-glass window depicting scenes from the Willoughby family history.
Willoughby became Chair of the Housing and Town Planning Committee and was one of the visionaries behind the scheme to redevelop the area which is now Ferensway. This never saw completion, as it was overtaken by scandals which centred around Willoughby. In 1932 he faced trial for demanding money with menaces from a firm of Hull tailors; he had extorted payments in return for contracts for tramway uniforms. At the same time an enquiry was initiated into the purchase of land for housing estates. The Thorpe enquiry was set up on March 3rd 1932. On the same day Willoughby went to Scotland, booked into a hotel in Helensburgh, Glasgow and was found on March 4th having committed suicide by gas. When the enquiry reported, on April 18th 1932, it was shown that Willoughy had been using his insider's knowledge of what land the council wished to buy to approach the owners himself and offer to find a buyer for a 4% commission. He would deny that it had anything to do with the Corporation. In one of the four cases examined he had taken a fee for finding a buyer for land on Endike Lane; the buyer was Alderman Francis Finn. A complicated bit of dealing that involved a builder, Robert Tarran, ended with the land being sold on to the Corporation at a profit for the three men involved. The report said, “The system of turning information into money had become a business pursued almost to recklessness. In less than a month he had made over £1100, and it should have occurred to him that discovery was inevitable.”