By confirming Stewart Downing's move to West Ham United this week, Liverpool accepted a £14 million loss on the winger, just two years after signing him from Aston Villa.
Along with Andy Carroll and Jordan Henderson, the Anfield giants have made some significant losses in the transfer market in recent times, with Downing, Carroll and Henderson considered to be three of the worst transfers in Liverpool's history - though in fairness, the latter has started to perform on a more consistent basis.
So, with thanks to talkSPORT, here we run down some of Liverpool's other expensive flops - and believe me there has been a few!
Disagree with any of the choices? Think someone else is more deserving of the title? Have your say in the comments box provided!