3=. Alberto Aquilani
Bought for: £20m by Liverpool in 2009
Sold for: Nominal fee to Fiorentina in 2012
Liverpool quickly feature again in a double effort of despair at number three, with Italian playmaker Alberto Aquilani's expensive switch to Anfield effectively a disaster from the word go.
Aquilani started just nine Premier League games for the Reds and was never given a proper run of matches to show the talent that regularly gives him a starting berth for the Italian national side, before being allowed to join Juventus and then Fiorentina in short-term loan spells.
The Reds eventually took a massive hit on the midfielder when he joined Fiorentina permanently for a nominal fee in 2012, with a reactionary transfer policy at Anfield in the recent past once again understandably called into question.