A factor in Lewington's managerial life was the presence of a high-profile chairman, Jimmy Hill, who, despite his protestations to the contrary, was assumed to have some involvement in team affairs.
Certainly, when the team was sliding towards the Fourth Division in 1989-90, the arrival at the Cottage of Alan Dicks as a 'consultant' with half a dozen games to go was at the chairman's instigation.
Hill and Dicks (a half back with Chelsea, Southend and Coventry in the 1950s and early 1960s) had been manager and coach respectively at Coventry in the 1960s, after which Dicks as manager had taken Bristol City into Division One. When the slide back down the divisions, and towards bankruptcy, started at Ashton Gate, Dicks went off to work in Greece, Cyprus, Qatar and the United States. His appearance at the Cottage in the spring of 1990 was his first involvement in British football for a decade, and it showed.
By the start of the 1990-1 season, Dicks was manager and Lewington his assistant, but the club's fortunes sank even lower. Behind the scenes, the battle to save the Cottage took a new twist, and a consequence was the injection of money to buy new players.
The fees that were paid and the contracts that were negotiated showed how out of touch Dicks had become. This was even more apparent in his relationship with the players.
Simon Morgan has revealed that whilst Dicks was liked as a person, few players had any respect for his managerial abilities or tactical knowledge. There was no discipline, team talks were incomprehensible, preparations were negligible and tactically the players were left to improvise.
Morale was at rock bottom and the humiliation of a Cup defeat by non-League spelt the end for Dicks in November 1991.