10 Most Expensive Transfer Flops In Liverpool History

4. Stewart Downing

If signing Adam was one of Dalglish's biggest errors during his second spell as Liverpool manager between 2011 and 2012, his decision to sign Stewart Downing for a whopping £18.5m in July 2011 was equally baffling. The winger had clearly always had talent, but to spend that much on a player who had always flattered to deceive was a huge risk that, ultimately, backfired. Downing's debut season was very unproductive, with the then 27-year-old astonishingly not registering one goal or assist in his 36 Premier League appearances. He often looked very low on confidence, and there was just no imagination to his game whatsoever. Although the 2012/13 campaign was slightly better- new manager Brendan Rodgers gave him the chance to prove himself- he still only scored five and created nine goals in his 45 matches. Rodgers had seen enough, and he sold Downing to West Ham in the summer of 2013. Now 30, he is playing very well at Upton Park. The reason for that is because he is a mid-table Premier League player, not someone who is capable of shining at a club with top four aspirations.