Andy Carroll (Liverpool £35m)
Everyone was surprised to see the former Newcastle striker – with a fairly average record at best, for his former club – move to Anfield for a fee of £35m. Carroll struggled to make the step up to Liverpool, and only returned six league goals in over 4o appearances, before a loan move to West Ham in 2012. The deal was made permanent a year later, with the Reds making a loss of £20m.