There's really only one place to start here, and that's with Ade Akinbiyi. The powerful striker had a growing reputation in the late 90's - and Leicester fell for it. 70 goals in 161 games during spells with Gillingham, Bristol City and Wolverhampton Wanderers led to a whopping £5.5m move to Filbert Street in what proved to be one of the most catastrophic Premier League transfers of all time.
In 18 months with the Foxes, Akinbiyi scored just 13 goals in 67 games before being sold to Crystal Palace for £2.2m. Akinbiyi will forever go down as one of the biggest wastes of money in Premier League history.
Eadie was a talented player but his career was cut short by injuries at the age of 28. Martin O'Neill forked out around £3.5m to sign the midfielder from Norwich in 1999, but played just 40 games in four years with the club before hanging up his boots in 2003. For the amount of money paid, Leicester just didn't get the most out of Eadie's short stay with the club.
A highly rated youngster at Leeds, Matt Jones made the move to Leicester at the age of just 20, with the Foxes paying £3m to land him. Jones had been brought in to replace Neil Lennon in the Leicester midfield, but much like Eadie, just couldn't stay fit and was forced to retire at just 23. Whilst he made a brief comeback with Llanelli in 2007, the Welshman's career is a story of what could have been.
After 40 goals in two seasons for Cambridge United, Trevor Benjamin was tipped for big things, and Leicester believed it too when they paid £1.3m to sign him in July 2000. Yet in four-and-a-half years with the Foxes, Benjamin scored just 12 goals, and has gone on to lead the most nomadic of careers. With 25 clubs since leaving Filbert Street in 2005, Benjamin never lived up to his potential.
Midfielder Lewis may have only cost £150,000, but how manager Peter Taylor thought Lewis was good enough for the Premier League is a mystery. Signed from Taylor's former club Gillingham, Lewis played just 30 games for the Foxes, and is considered by fans to be one of the worst players to play for the club having struggled to adapt to top flight football.