10 Most Expensive Transfer Flops In Premier League History

4. Alberto Aquilani

Liverpool have had a few transfer shockers down the years, and the signing of Aquilani in the summer of 2009 was easily one of the worst. With Xabi Alonso having departed for Real Madrid, much to the dismay of Reds fanatics everywhere, a truly top class playmaker was needed to come in and fill the void. Benitez opted for the Italian, signing him for £17.1m from Roma. His time on Merseyside was to be a complete disaster though. Aquilani arrived at Anfield carrying a relatively long-term injury, and he didn't make his debut until November 2009, in a League Cup clash with Arsenal. Despite the odd rare bit of quality here and there, it was clear to see that he was both nowhere near Alonso's level, or cut out for the Premier League. He lacked pace, power, tenacity and general influence. The Italian scored two goals in 26 appearances in 2009/10, and he spent the next two years on loan, firstly at Juventus then at AC Milan. He returned to Liverpool for pre-season in the summer of 2012, but Brendan Rodgers was clearly not impressed by him and he was swiftly sold to Fiorentina on a permanent deal. Aquilani has to go down as one of Liverpool's worst ever signings.