#8 Paolo Di Canio - £1.5m (Sheffield Wednesday to West Ham, 1999)
By 1999, transfer fees hadn’t quite reached the heights they’ve done today, but a lot of money was still being spent on players, particularly in the Premier League.
At the time of Paolo Di Canio’s £1.5m move from Sheffield Wednesday to West Ham, the British transfer fee record stood at £15m – paid by Newcastle for Blackburn’s Alan Shearer in the summer of 1996.
Sure, Di Canio was 30 at the time of his move, but he was still a hugely talented forward who’d played for Italian giants Lazio, Juventus, Napoli and AC Milan, and his debut season in the Premier League saw him score 12 goals for the Owls and be named as their Player of the Year. So how did the Hammers sign him for a fee that in no way reflected his playing ability?
Well, for a simple reason; at the time of his move, Di Canio was considered damaged goods in the English game, as the first half of the 1998-99 season had seen him slapped with an 11-match ban after he was red carded and then shoved referee Paul Alcock to the ground during Wednesday’s game with Arsenal.
Despite his fiery reputation, Hammers boss Harry Redknapp clearly felt he was worth the risk – the cheap transfer fee probably helped – and he turned out to be right.
Di Canio went on to spend 4 and a half seasons at Upton Park, scoring 47 goals in the process and helping the club to make European competition for the first time in years – and never became embroiled in controversy throughout his time there.