#4 Javier Mascherano (West Ham to Liverpool - £20 million - February 2007)

Exactly what the deal was between West Ham and Liverpool for the transfer of Mascherano is still unclear. There is no doubt, though, as to how great a signing Mascherano proved to be for Liverpool.
He progressed from a highly rated player to a star defensive midfielder in his time at Liverpool which finally lead to his move to Barcelona in the summer window of 2010.
Mascherano may not have won titles at Liverpool (he did well for himself at Barcelona though, obviously) but he was a stellar signing and Liverpool midfield has never been the same since the departure of Mascherano and Xabi Alonso.
Best season at Liverpool - 2008/09 (27 goals conceded and Liverpool finished 2nd in the Premier League)
Liverpool of 2008/09 were an incredibly fun team to watch with Fernando Torres and Steven Gerrard in their prime. They lost only 2 games throughout the PL campaign but were done in by 11 draws conceding only 27 goals.
They finished the campaign in the 2nd position at 86 points behind Manchester United's 90 points. This was the closest Liverpool had come to the title in many years and while the attacking flair of Gerrard and Torres are remembered best, the role of Mascherano and Alonso was more critical to their success as the departure of the duo proved to be the undoing of the club.