10. Paolo Di Canio – Sheffield Wednesday to West Ham United: £1.5m
The enigmatic Paolo Di Canio had already turned out for the likes of Lazio, Juventus, Napoli and AC Milan before he eventually upped sticks and left his homeland for Celtic in 1996.
The Italian enjoyed instant success in Scotland, winning the SPFL Player of the Year having banged in 15 goals during his debut season – attracting interest from a number of Premier League clubs, including eventual suitors Sheffield Wednesday.
Owls Manager David Pleat flew to Glasgow to see the Celtic number 7 in action before preparing a bid. Di Canio turned out to be injured on the day, but conversations that the Sheffield Wednesday Manager had with three different Glaswegian taxi drivers during his trip convinced Pleat to advise his Chairman to part with £4.2m to secure the Italian’s services.
Once more, Di Canio thrived at his latest club. Top scorer for Wednesday in his debut season, he was an instant hit with the Hillsborough faithful. Until that fateful day he decided to push referee Paul Alcock to the ground during a home game against Arsenal. An inevitable red card followed, then a £10,000 fine and a 10-match ban.
Di Canio didn’t kick a ball from that August Alcock altercation until the following January, when West Ham United boss Harry Redknapp took a £1.5m gamble on the Italian.
His time at Upton Park was not without controversy. However, Di Canio will always be remembered fondly in East London for a number of iconic moments. That winning goal against Fabian Barthez at Old Trafford, the scissor-volley against Wimbledon, catching the ball when presented with an open goal at Goodison Park.
In previous seasons, the Hammers had signed players such as Richard Hall and Joey Beauchamp for similar fees. With almost £3m taken off the price that Sheffield Wednesday had spent on Di Canio just eighteen months prior to his arrival in London, the charismatic number 10 has to go down as West Ham’s best Premier League signing and will be remembered as one of the greatest players to have turned out for the club.