The exit of Xabi Alonso to Real Madrid in the summer of 2009 was one of the biggest blows to Liverpool over the past decade. The brilliant Spaniard had become a legend at the club, and his influential displays in the centre of midfield would be missed dearly. Benitez needed to replace him with a world-class player, but instead he opted for Aquilani. The Italian was signed for £17.1m from Roma, and was seen as a silky, technical midfielder who could pick a pass and dictate a game. He arrived at Liverpool carrying an injury, which was an immediate issue, and the Reds' lack of depth in midfield saw their 2009/10 campaign get off to a terrible start without him. He didn't make his debut until the end of October, but when he did get a run in the side his performances were just nowhere the quality of Alonso's. Benitez's men failed to make it past the Champions League group stages, with Aquilani struggling in the pivotal loss to Fiorentina, and by the end of the season he had been limited to 26 mediocre displays. He would never play another competitive game for the club. He was sent on loan to Juventus and AC MIlan, in 2010/11 and 2011/12 respectively, and having been deemed surplus to requirements by new Reds boss Brendan Rodgers in the summer of 2012, he was sold to Fiorentina. It bought an end to one of the most disappointing Liverpool careers in recent memory.