3=. Andy Carroll
Bought for: £35m in January 2011
Sold for: £15m to West Ham United in 2013
Liverpool manager Kenny Dalglish's capture of Andy Carroll still draws a wry smile from rival opposition to this day, with the Reds boss backing the young England international to the tune of £35m.
Carroll never came close to justifying a hefty price tag that weighed heavy at Anfield, joining West Ham on loan last season with new Reds boss Brendan Rodgers deciding to favour other forwards.
The 25-year-old completed a permanent £15m move to Upton Park last summer, ending an ill-fated Liverpool spell before spending six months on the sidelines with a persistent heel injury as the Reds were left to ponder a £20m loss.