The top 12 biggest Liverpool transfer disappointments

19 Mar 2002: Jari Litmanen of Liverpool celebrates after scoring the first goal with a penalty during the Liverpool v AS Roma UEFA Champions League, Group B match at Anfield, Liverpool. DIGITAL IMAGE. Mandatory Credit: Shaun Botterill/Getty Images
19 Mar 2002: Jari Litmanen of Liverpool celebrates after scoring the first goal with a penalty during the Liverpool v AS Roma UEFA Champions League, Group B match at Anfield, Liverpool. DIGITAL IMAGE. Mandatory Credit: Shaun Botterill/Getty Images /
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LIVERPOOL, ENGLAND – DECEMBER 15: Joe Cole of Liverpool in action during the Barclays Premier League match between Liverpool and Aston Villa at Anfield on December 15, 2012 in Liverpool, England. (Photo by Clive Brunskill/Getty Images)
LIVERPOOL, ENGLAND – DECEMBER 15: Joe Cole of Liverpool in action during the Barclays Premier League match between Liverpool and Aston Villa at Anfield on December 15, 2012 in Liverpool, England. (Photo by Clive Brunskill/Getty Images) /

Joe Cole

Former Chelsea winger Joe Cole arrived on a free transfer and is another big ‘what if’. Despite possessing bags of talent, it never worked out at Anfield and Cole was probably past it by then anyway.

His first ever game for Liverpool ended in disaster when the winger was sent off against Arsenal and things never really got better for him from there.

Cole only started a small percentage of competitive games in his first reason on Merseyside, and as Aygers said on that Reddit thread ‘never seemed to be bothered to play for us. Didn’t help that Woy was the manager, the whole club was in disarray at that time.’

After leaving Liverpool, Cole went on to blast the club. “I can only play for teams that I’m passionate about and I think that’s what went wrong for me at Liverpool,” ESPN reported that he said. “I didn’t feel a connection with the club or the place that I had at Chelsea and West Ham.”