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The top 12 biggest Liverpool transfer disappointments

Russell Hughes
Russell Hughes

Rush The Kop

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
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

Football fans the world over are used to transfer disappointments and Liverpool is no different.

The club has had a few over the years, but this list look at 12 that hurt supporters the most. Not because they were the worst, but because they just didn’t work quite as they wanted.

That could have been for a number of reasons – perhaps they never bedded in properly or hit the heights that were expected. Maybe they were played out of position, or sold too early.

Whatever the reason, fans invest a lot of emotional energy in football and in new arrivals and it can hurt when it doesn’t work out.

And it’s for that reason that you’ll find players who had an okay career at Anfield on this list, but perhaps never played to the best of their talent.

So scroll down through this list to read about 12 of the biggest Liverpool transfer disappointments and read about the justification via this Reddit feed.

EINDHOVEN, NETHERLANDS – DECEMBER 09: Robbie Keane of Liverpool looks on during the UEFA Champions League Group D match between PSV Eindhoven and Liverpool at the Philips Stadium on December 9, 2008 in Eindhoven, Netherlands. (Photo by Ryan Pierse/Getty Images)
EINDHOVEN, NETHERLANDS – DECEMBER 09: Robbie Keane of Liverpool looks on during the UEFA Champions League Group D match between PSV Eindhoven and Liverpool at the Philips Stadium on December 9, 2008 in Eindhoven, Netherlands. (Photo by Ryan Pierse/Getty Images)

Robbie Keane

Irish striker Robbie Keane was only given six months at Liverpool before being sold back to Tottenham Hotspur.

There is an air of mystery around the signing and why it didn’t last very long, but one thing is for sure: fans never ever saw the best version of Keane.

With 19 league appearances and five goals, things never really clicked for the Republic of Ireland international.

Keane blamed manager at the time Rafa Benitez for his failure. “He [Benitez] wanted to change me to a left winger and I mean I am clearly not a left winger, and that is obviously clear for everyone to see,” the Daily Star reported that the striker complained.

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.”

HULL, ENGLAND – MAY 9: Alberto Aquilani of Liverpool during the Barclays Premier League match between Hull City and Liverpool at the KC Stadium on May 9, 2010 in Hull, England. (Photo by Jed Leicester/Getty Images)
HULL, ENGLAND – MAY 9: Alberto Aquilani of Liverpool during the Barclays Premier League match between Hull City and Liverpool at the KC Stadium on May 9, 2010 in Hull, England. (Photo by Jed Leicester/Getty Images)

Alberto Aquilani

Italian midfielder Alberto Aquilani was supposed to be the answer to Liverpool’s midfield problems after Xabi Alonso left, but Aquilani failed miserably and will be forever remembered as a flop.

Injuries were probably the main reason the Roma man never took off at Anfield. He somehow passed a medical despite not playing for months due to an ankle problem.

After making a brief debut in November, Aquilani finally made his full debut in December and went on to register six assist for the campaign. Not a bad return given how little he played.

But his time on Merseyside didn’t last long and the Italian returned to him homeland with AC Milan and Juventus – leaving a giant pile of ‘what ifs’ behind him.

LIVERPOOL, UNITED KINGDOM – MARCH 08: Fernando Morientes of Liverpool looks dejectedly at the turf during the last 16 2nd leg UEFA Champions League match between Liverpool and Benfica at Anfield on March 8, 2006 in Liverpool, England. (Photo by Alex Livesey/Getty Images)
LIVERPOOL, UNITED KINGDOM – MARCH 08: Fernando Morientes of Liverpool looks dejectedly at the turf during the last 16 2nd leg UEFA Champions League match between Liverpool and Benfica at Anfield on March 8, 2006 in Liverpool, England. (Photo by Alex Livesey/Getty Images)

Fernando Morientes

Former Real Madrid striker Fernando Moreintes joined Liverpool as Michael Owen was making the opposite trip, but never hit the heights that were expected of him.

With 112 La Liga goals in less than 300 appearances, the Spanish international looked to be a high-class player who could make an impact, but in 41 Premier League games he only scored eight goals and never established himself as a key first team member.

Everyone was excited when Morientes arrived and could see his quality, but he never took off in England and that will forever be a huge disappointment for fans.

After 18 frustrating months, he was moved on back to his homeland, leaving Liverpool fans to scratch their heads and try to work out what went wrong.

Lazar Markovic

When Brendan Rodgers signed Serbian Lazar Markovic from Benfica, he tried to convince the world that Liverpool had just landed someone with world-class potential.

A lack of opportunities seem to have stunted his progress, something that Reddit users agree with. “Early on he kept showing flashes of talent, the kind which usually suggest a bright figure, then so few opportunities he just didn’t progress,” said Every_Geth.

After a range of loan moves that never seemed to work out, Markovic is back in the first team squad but it looks like he won’t play for the first team.

With plenty of options out wide, this looks like it will go down in the record books as another giant missed opportunity.

8 Aug 2001: Markus Babbel of Liverpool is challenged by Ilro Aalto of FC Haka during the UEFA Champions League Third Qualifying Round, First Leg game between FC Haka and Liverpool at the Olympic Stadium in Helsinki, Finland. DIGITAL IMAGE. Mandatory Credit: Ross Kinnaird/ALLSPORT
8 Aug 2001: Markus Babbel of Liverpool is challenged by Ilro Aalto of FC Haka during the UEFA Champions League Third Qualifying Round, First Leg game between FC Haka and Liverpool at the Olympic Stadium in Helsinki, Finland. DIGITAL IMAGE. Mandatory Credit: Ross Kinnaird/ALLSPORT

Markus Babbel

This looked like it could have been one of the best free transfers in Liverpool history, but then fate swooped in and robbed the club of an excellent player.

A highly successful time in Germany with Bayern Munich culminated in Real Madrid making an approach for the German, which he rejected in favour of coming to Anfield. What a legend!

But then Guillan-Barre syndrome struck down Babbel. After being left in a wheelchair, it took the defender 15 months to complete rehabilitation and return to football.

However, his return was not a happy one and the German struggled with discipline and fitness issues – understandably so. Eventually he was moved on to Blackburn Rovers and then back to the Bundesliga with Stuttgart.

MANCHESTER, UNITED KINGDOM – DECEMBER 30: Dietmar Hamann of Manchester City is challenged by Harry Kewell of Liverpool during the Barclays Premier League match between Manchester City and Liverpool at The City of Manchester Stadium on December 30, 2007 in Manchester, England. (Photo by Alex Livesey/Getty Images)
MANCHESTER, UNITED KINGDOM – DECEMBER 30: Dietmar Hamann of Manchester City is challenged by Harry Kewell of Liverpool during the Barclays Premier League match between Manchester City and Liverpool at The City of Manchester Stadium on December 30, 2007 in Manchester, England. (Photo by Alex Livesey/Getty Images)

Harry Kewell

Australian winger Harry Kewell could have been so much more. After being voted Premier League Young Player of the Year for 99/00, Liverpool snapped him up for £5 million after Leeds United suffered financial ruin.

After a good debut season, injuries began to take their toll on the player – who would fluctuate between being able to play and sitting on the sidelines.

The list of ailments that Kewell suffered where lengthy, including septic arthritis – and the Aussie only played 93 times in the league five seasons. Tellingly, 62 of those appearances came in two campaigns.

A tricky winger who could terrorise defences as well as possessing a good eye for goal, the former Leeds man never achieved what he was capable at Liverpool and that will forever be a great shame.

SWANSEA, WALES – MAY 01: Christian Benteke of Liverpool celebrates scoring his team’s opening goal during the Barclays Premier League match between Swansea City and Liverpool at The Liberty Stadium on May 1, 2016 in Swansea, Wales. (Photo by Stu Forster/Getty Images)
SWANSEA, WALES – MAY 01: Christian Benteke of Liverpool celebrates scoring his team’s opening goal during the Barclays Premier League match between Swansea City and Liverpool at The Liberty Stadium on May 1, 2016 in Swansea, Wales. (Photo by Stu Forster/Getty Images)

Christian Benteke

Another striker who came to the club with a good record is Belgian Christian Benteke, but he was never going to fit in with the club’s style and failed to flourish at Anfield.

Benteke got everyone’s hopes up after some excellent years at Aston Villa, but he looked like a square peg in a round hole and was swiftly jettisoned under Jurgen Klopp.

His strengths were not suited to the way the Reds played and despite a strong start to his career, the goals dried up along with his confidence.

Crystal Palace soon came calling for the bruiser, and who knows what would have happened had he moved to a team whose style was more suited to his play.

28 Dec 1998: Karl-Heinz Riedle of Liverpool celebrates his goal with Michael Owen during the FA Carling Premiership match against Newcastle United played at Anfield in Liverpool, England. The match finished in a 4-2 victory for Liverpool. \ Mandatory Credit: Clive Brunskill /Allsport
28 Dec 1998: Karl-Heinz Riedle of Liverpool celebrates his goal with Michael Owen during the FA Carling Premiership match against Newcastle United played at Anfield in Liverpool, England. The match finished in a 4-2 victory for Liverpool. \ Mandatory Credit: Clive Brunskill /Allsport

Karl-Heinz Riedle

What is the deal with strikers and disappointing those around them? There seems to be so much guesswork around the science of bringing in players to score goals, and Karl-Heinz Riedle is another that didn’t work out.

“I hadn’t heard that name in a long time. I thought that he would be an excellent Premiership centre forward. Such disappointment,” summed up C_stat.

76 appearances across three seasons and 15 goals was the sum of Riedle’s stay on Merseyside as he made the trip to London to play for Fulham.

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

Jari Litmanen

Finnish striker Jari Litmanen emerged out of the Netherlands as one of the best players in the world, yet when he left Liverpool he was a shadow of his former self.

Litmanen moved to Barcelona on a free transfer before the Reds finally signed him at the third time of asking, but an ankle injury meant Gerard Houllier was reluctant to play the Finn.

After just two seasons at the club, he moved back to Ajax after played 43 times across both campaigns. Strangely, Houllier had praised him to the hilt upon signing Litmanen, but then hardly played him.

This one could have turned out so differently had the forward been managed a bit better, but we’l never know.

HULL, ENGLAND – APRIL 28: Tom Huddlestone of Hull City and Mario Balotelli of Liverpool clash during the Barclays Premier League match between Hull City and Liverpool at KC Stadium on April 28, 2015 in Hull, England. (Photo by Laurence Griffiths/Getty Images)
HULL, ENGLAND – APRIL 28: Tom Huddlestone of Hull City and Mario Balotelli of Liverpool clash during the Barclays Premier League match between Hull City and Liverpool at KC Stadium on April 28, 2015 in Hull, England. (Photo by Laurence Griffiths/Getty Images)

Mario Balotelli

Should Mario Balotelli have made this list? His potential was definitely there, and in that respect his failure was certainly a disappointment to fans. However, all the signs that we wouldn’t were there – so can we really class it as a disappointment rather than a poor buy?

Well to some fans it should be. The Italian had shown extraordinary flashes of quality during his time with the national side and Manchester City and Brendan Rodgers was well within his rights to roll the dice.

But this is a deal that never looked good. Balotelli hardly played, hardly scored and was an all round waste of money and talent.

LIVERPOOL, ENGLAND – OCTOBER 07: Steven N’ Zonzi of Stoke City challenges Nuri Sahin of Liverpool during the Barclays Premier League match between Liverpool and Stoke City at Anfield on October 7, 2012 in Liverpool, England. (Photo by Clive Brunskill/Getty Images)
LIVERPOOL, ENGLAND – OCTOBER 07: Steven N’ Zonzi of Stoke City challenges Nuri Sahin of Liverpool during the Barclays Premier League match between Liverpool and Stoke City at Anfield on October 7, 2012 in Liverpool, England. (Photo by Clive Brunskill/Getty Images)

Nuri Sahin

Was this one Rodger’s fault or Nur Sahin’s? The Borussia Dortmund man is definitely a good player, so was he just unlucky and horribly played out of position?

“Amazing loan that fell in our lap, but Brendan played him out of position and they kind of fell out. Loan cancelled by January. I was pretty bummed about that,” said konja04.

The playmaker certainly could have made Liverpool a better team, but he was played in the wrong role over and over again.

Next: Liverpool’s 32 Best Signings Under Brendan Rodgers

Sahin then proved his quality by going to Germany and turning it on for Klopp at Dortmund. Brendan, this one is on you.

Russell Hughes

Russell Hughes

South Africa born, England raised and New Zealand living but my writing is less confusing than my residency status.