7) Stewart Downing – £18.5 million (Failure)
Bought off the back of impressive spells with Middlesbrough and Aston Villa, Downing had a fairly miserable two years at Anfield, despite playing almost 100 games. Brendan Rodgers deployed Downing as a left-back after taking over the manager’s reigns from Kenny Dalglish, before eventually allowing him to leave for £5 million to West Ham United in 2013.