10 Most Expensive Transfer Flops In Liverpool History

2. Alberto Aquilani

It is well-known by now that the summer of 2009 was a critical one at Liverpool. They had come second in 2008/09, and many people felt they could win the Premier League in 2009/10. Xabi Alonso, one of the most influential players at the club, had left for Real Madrid, and Benitez had to replace his playmaker with someone of similar ability. He bought in Alberto Aquilani for £17.1m, but the fact that he had been carrying an ankle injury for several months was not exactly ideal by any means. He didn't make his Reds debut until October 2009, in a League Cup clash with Arsenal, and when he did play the chasm in class between himself and Alonso was alarming. He couldn't dictate games, he was often very unnoticed and just two goals in 26 appearances was a very poor return for a relatively attacking midfielder. He was shipped out on loan to Juventus and AC Milan, in 2010/11 and 2011/12 respectively, before returning to Liverpool for pre-season training. Rodgers clearly didn't see him as part of his plans, however, and the Italian made a permanent move to Fiorentina in time for the 2012/13 campaign. To say his time on Merseyside was a disaster would be the understatement of the century.