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#3 Alberto Aquilani - £17.1 million, 2009
In hindsight, Alberto Aquilani's Liverpool career was a summation of the club itself during their "banter years", when the Reds suffered their worst spell of football in recent memory.
Signed from Roma, Aquilani arrived at Anfield in 2009 with some promise and was expected to take over from the departing Xabi Alonso.
Not only did he spectacularly fail at filling the Spaniard's shoes, but his performances also left the Anfield faithful dismayed more often than not. Three years (and not one great performance) later, the Italian was sold to Fiorentina for just €790,000 in 2012.
The former Roma player made 18 Premier League appearances for the club over three years. To give this some context, each league appearance cost Liverpool over £1M in terms of transfer fees and salary. The Italian was plagued with injuries and did not have a single memorable game at Anfield, and the fans were more than happy to see his departure.
