(#9 Paolo Di Canio (West Ham))
At £1.5 million, Di Canio was not exactly a costly acquisition but the fiery Italian did pose some risk. After all, he had just completed an 11 game ban for pushing over referee Paul Alcock during a Premier League game between Sheffield Wednesday and Arsenal. Joining the Hammers at the age of 31 in 1999, he instantly became a fan favourite. During his first season with the club, he was named Player of the Year and his flying volley against Wimbledon in March 2000 is still considered one of the greatest Premier League goals of all time. He stayed at Upton Park for four years scoring 47 goals in 118 games but was not able to steer the club clear of relegation at the end of the 2002/03 season. He later joined Charlton Athletic on a free transfer but his time with the claret and blues will always be remembered fondly.