4) Alberto Aquilani
When Liverpool sold the brilliant Xabi Alonso to Real Madrid, they signed Italian Roma midfielder Aquilani to replace him. The problem was, Aquilani was crocked, and after signing for £18m, he didn’t play until halfway through his first season in 2009/10. Even more bizarrely, once he proved hits fitness, he was shipped out on loan to Italy – where he actually did pretty well. He was then permanently got rid of on a free in 2012. What a waste!