A self-made millionaire, he previously built up a free local newspaper business, making his fortune primarily from the advertising revenue it generated.
[citation needed] In January 1992, with Arthur Cox's low budget team just in touch with the leading pack, Pickering embarked on a spending increase, the biggest in the club's history, with the £1million signing of Marco Gabbiadini from Crystal Palace.
Derby were relegated from the old First Division the year Pickering bought the club, and suffered two playoff defeats over the next three seasons which saw them miss out on a place in the new FA Premier League.
With a string of new signings and the hiring of future England and Derby County head coach, Steve McClaren as assistant manager, Smith took the club to the promotion in his first season.
As the club's fortunes levelled off and subsequently began to slump in the early 2000s, there was a moderate amount of disquiet amongst fans.