Ranking the 20 Worst Transfer Deadline Day Moves in History

Karl Matchett@@karlmatchettFeatured ColumnistJanuary 31, 2014

Ranking the 20 Worst Transfer Deadline Day Moves in History

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    Transfer deadline day is upon us and around the country, teams will be hoping to seal a late deal to add that vital component to their squad who might aid a title push, seal a European place or perhaps even avoid relegation.

    Unfortunately they don't always go quite to plan, especially when deals and decisions have to be rushed on deadline day—perhaps with a crucial detail or two overlooked or the odd few million (or more) spent too hurriedly.

    Here are the 20 worst deals completed by Premier League clubs on deadline days since the transfer window's introduction in 2002-03.

20. Wayne Bridge, Manchester City to Sunderland (loan), 2012

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    There's no doubting Wayne Bridge was a talented left-back, but a long succession of seasons playing second fiddle ruined his career, effectively leaving him to plod from club to club after all other targets had been blocked.

    City paid £11.5 million for him in 2009, but he only ended up playing 58 times for them in four years.

    Loan spells everywhere proved no particular success, but the deadline day move to Sunderland was particularly atrocious. Bridge played 10 times (half of those as substitute), committed bad errors with regularity and only completed one 90-minute game.

19. Owen Hargreaves, Free Agent to Manchester City, August 2011

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    Manchester United released Owen Hargreaves in the summer of 2011 after an injury-hit time, only for local rivals Manchester City to snap him up themselves.

    They were convinced after a rigorous medical that he could play a part in their squad—though they only gave him a one-year deal.

    The England international made a grand total of one Premier League appearance for them, was released on a free transfer again and retired.

18. Bryan Ruiz, FC Twente to Fulham, August 2011

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    Fulham broke their transfer record in 2011 to bring flamboyant forward Bryan Ruiz to the Premier League, paying around £12 million to FC Twente.

    The Costa Rican had scored 33 league goals in his last two seasons in Holland, but managed a paltry two in his debut campaign in England.

    Five last season wasn't much better. Despite showing flashes of his genius, he has never been consistent enough—and has been loaned out to PSV during this transfer window.

17. Hossam Ghaly, Feyenoord to Tottenham Hotspur, January 2006

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    Spurs looked to Holland to pluck Egyptian midfielder Hossam Ghaly from Feyenoord on deadline day of the January 2006 window, but it wasn't a long-lasting relationship.

    He managed only 34 league appearances for Tottenham before being released on a free to Derby County after throwing his shirt to the ground in a tantrum after being substituted, having come on as a sub himself earlier in the game.

16. Javier Mascherano, Corinthians to West Ham United, August 2006

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    To this day nobody seems quite sure how Carlos Tevez and Javier Mascherano ended up at West Ham United.

    The bizarre transfers themselves aside, while Tevez eventually got a run in the team, manager Alan Pardew seemingly had no notion of how to get Mascherano into his side. The midfielder made just seven league appearances for the Hammers before he lost his place in the side entirely.

    Then he was loaned to Liverpool in January and promptly went on to feature in the Champions League final.

    A year after that, the loan deal was made permanent and eventually the seven-time West Ham player went on to play for Barcelona too. Hmmm.

15. Asamoah Gyan, Rennes to Sunderland, August 2010

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    Who knows where this one went all wrong?

    Asamoah Gyan enjoyed a good debut season with Sunderland after joining in 2010, hitting 10 goals in 31 games and being a big part of the team.

    The next season, though, the Ghanian forward played three games, didn't score—then decided to leave the Premier League for the bright lights of...Al-Ain FC. He's been there since, having completed a big-money permanent deal.

14. Benni McCarthy, Blackburn Rovers to West Ham United, January 2010

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    West Ham needed a striker to help them try to avoid relegation in 2010, so it was perhaps reasonable to look to South African legend Benni McCarthy.

    The problem was, by the time he arrived at the Hammers he was overweight, out of shape and never looked like the answer to West Ham's problems.

    He lasted barely more than a year at Upton Park, played just 14 games and failed to score a single goal before being released on a free.

13. Andre Santos, Fenerbahce to Arsenal, August 2011

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    Arsenal spent most of deadline day in the summer of 2011 scrabbling about for new signings, but Andre Santos was not quite one of the better decisions made that day.

    The former Fenerbahce man cost a little over £6 million but lasted just 18 months at the club before being shipped back to Brazil with Gremio and then Flamengo.

    He rarely put in the sort of performances expected of him at the Emirates, making just 33 league appearances all told.

12. Eric Djemba-Djemba, Manchester United to Aston Villa, January 2005

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    It was easy to see why Aston Villa wanted to sign Eric Djemba-Djemba after his stunning success with Manchester United.

    Or, alternatively, it was easy to see why the Cameroonian midfielder played just 11 league games for the Villains after his £2 million move, was loaned out to Burnley and eventually sold on a free.

11. Robinho, Real Madrid to Manchester City, Summer 2008

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    Manchester City wanted to make their mark on the transfer market when they were taken over, and Brazilian forward Robinho was the £30 million-plus flagship signing on deadline day in 2008.

    He had a good first season and scored 14 goals, but form and attitude both seemed to take a steep nosedive thereafter, with the former Real Madrid man failing to score in 10 league games the next season before being loaned back to Brazil.

    The following summer Robinho was off to Italy, sold to AC Milan for a massive loss.

10. Djibril Cisse, Lazio to Queens Park Rangers, January 2012

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    "Explosive" might best describe Djibril Cisse's time at QPR.

    He joined on deadline day in 2011 to try and keep Rangers up, for around £4.5 million.

    Cisse did score, six times in fact, but also managed to get himself sent off twice, missing seven of 16 games through suspension as a result. The next season he started 12 games but scored just three in the first half of the season and was deemed surplus to requirements. He headed off to Al-Gharafa on loan and QPR were relegated. 

9. Paul Konchesky, Fulham to Liverpool, August 2010

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    Former Liverpool boss Roy Hodgson opted to bring his old left-back from Fulham with him in 2010, signing Paul Konchesky for the Reds.

    For the left-back's services he paid more than a few million, plus two young academy talents in Alex Kacaniklic and Lauri Dalla Valle.

    Konchesky played half a season, was shipped out on loan when Hodgson was sacked and now plays in the Championship for Leicester. Kacaniklic is a Sweden international.

8. Benjani Mwaruwari, Portsmouth to Manchester City, January 2008

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    A few months before Robinho signed, Manchester City were apparently desperate for any kind of a forward with some sort of goalscoring pedigree.

    For whatever reason, they therefore paid close to £5 million to Portsmouth for their forward Benjani Mwaruwari, who had hit 12 goals for Pompey that season.

    Benjani scored on his debut in the derby, but managed just two more all season. In total he played only 31 games (scoring seven) for City in the Premier League before spells at Sunderland and Blackburn ensued.

7. Andy Van Der Meyde, Inter Milan to Everton, August 2005

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    Everton handed former Ajax winger Andy van der Meyde a four-year deal when they signed him in 2005, but during that time he made a meagre 22 appearances.

    He was suspended and fined by the club multiple times for missing training or other disciplinary issues, was sent off in his first Merseyside derby and failed to score a single competitive goal.

    Van der Meyde was released on a free transfer, without a club at the time, in 2009.

6. Xisco, Deportivo La Coruña to Newcastle United, August 2008

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    Former Newcastle United striker Xisco is, would you believe, still only 27 years old. He currently plays for Segunda Division side Cordoba, having finally ended his long, nightmarish stay at St. James' Park a year ago.

    The Magpies paid £5 million for him from Depor in 2008, but signed him seemingly without then-manager Kevin Keegan knowing about it or being happy about it.

    In four-and-a-half years Xisco played just 11 times for Newcastle, scoring one goal, with three loan spells spent back in Spain in between. His contract was finally cancelled in January 2013, after which he returned to Spain permanently.

5. Christopher Samba, Anzhi Makhachkala to Queens Park Rangers, January 2013

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    QPR, battling relegation in 2012-13, spent big in the January window to try and aid their survival.

    Harry Redknapp identified Chris Samba as the man to shore up the defence and provide the organisation and leadership his team needed, and he sanctioned a £12 million move with wages of £100,000 per week going to the giant centre-back.

    He played 10 games in a row, with the team conceding 19 goals in that period, and was so disappointing he was dropped for the final four vital matches. QPR were still relegated.

    Samba moved back to Anzhi for the same fee in the summer, before immediately being sold to Dinamo Moscow as the Anzhi exodus began.

4. Afonso Alves, Heerenveen to Middlesbrough, January 2008

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    In 49 games, Afonso Alves scored 13 goals for Middlesbrough. Ten of them came in the Premier League over the course of a season and a half. That's what Boro got for their £14 million, and his four-goal return in the whole of the 2008-09 season was nowhere near enough to keep his team up.

    Boro were relegated and their big-money signing was off to Al-Sadd the following summer.

3. Andy Carroll, Newcastle to Liverpool, January 2011

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    Liverpool broke their transfer record twice in a few hours on deadline day in January 2011, the second of which was the £35 million signing of Newcastle striker Andy Carroll.

    Fitness issues blighted his year-and-a-half on Merseyside, when he was unable to find anything like his early Premier League form for the Reds. He managed just 11 goals in 58 games before being loaned out to West Ham United for a season.

    Carroll completed a permanent move to the Hammers in the summer, allowing Liverpool to recoup only about £15 million of their initial investment.

2. Michael Owen, Real Madrid to Newcastle United, August 2005

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    Newcastle United thought they might have the perfect front pair when they signed Michael Owen to play alongside Alan Shearer in 2005.

    The England striker got handed a four-year deal to come back to the Premier League from Real Madrid on massive wages and a £17 million transfer fee.

    Injury after injury followed, including a broken foot, a ruptured ACL, a double hernia and myriad leg muscle strains.

    All told, Owen made only 79 appearances for the Magpies—an average of less than 20 a season—and scored just 30 goals, averaging less than eight per season. He left on a free transfer when his contract expired, and Newcastle were left relegated, with Owen scoring only once in the second half of the campaign.

    All told, wages and transfer fee included, Owen cost Newcastle around £40 million or £1.3 million per goal.

1. Fernando Torres, Liverpool to Chelsea, January 2011

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    Earlier in the same day that Carroll moved to Liverpool, Fernando Torres vacated his place as the Reds' striker to move south to Chelsea for a British transfer record £50 million.

    Three years on, Torres has managed just 42 goals for the Blues in 154 matches—not even a goal every three-and-a-half games.

    Despite countless "he's back" storylines and half-hoped ideas, Torres has never shown anything like the form or consistency in blue that he managed in red and, now rapidly approaching his 30th birthday, is all but certain to fail to be the striker Chelsea thought they were signing.

    His best league tally for Chelsea in a season so far is a paltry eight goals—he actually managed nine in the half-season at Liverpool before leaving for his present team.

    Even after three years at Stamford Bridge, Torres has still cost his club an average of just about £1.2 million per goal, making him the worst deadline day Premier League signing since the transfer windows were introduced.