Andy Carroll (£35m):
The biggest blemish for a club of Liverpool’s stature is the fact that their most expensive signings remains their most ineffective high profile signings to date. After a fruitful time at Newcastle United and Preston, Liverpool decided to break the club record to add him to their squad but the international was just not able to get his career off the tracks at Anfield. He scored just 6 goals in 44 league appearances in his two years at the club and remains one of the worst transfer decisions by England’s most decorated team.