English Premier League: 40 of the Biggest Flops in Premiership History

Lee ThorpeContributor IIIMay 22, 2011

English Premier League: 40 of the Biggest Flops in Premiership History

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    As this season has now come to a close and teams go off on their holidays for a few weeks, the excitement starts to build again in fans as to just who their club will be buying in the summer. All the rumours and gossip in the papers gets fans drooling at the prospect of seeing Europe’s finest pull on their beloved team’s shirt.

    However, not all transfers work out like a beautiful marriage. You may have been excited when it happened, but what about at the end of the season? How about when your manager decides to splash all his cash on an ageing striker from Peru who hasn’t scored in two years? Let’s face it, there have been some bad ones!

    Now fans always have a debate and argue about how to define a "flop," but I’ve gone off players who have either failed to improve their club, cost their club too much money in the long run or players who are simply just not good enough for that team. It’s irrelevant how good they’ve become since moving on, I’m looking at them at that stage of their careers.  Also, players who suffered career ending injuries weren’t included.

    If you think I’ve missed any big players out, let me know!

40. Per Kroldrup. Udinese to Everton. £5 Million

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    This was a strange one. Everton aren’t known for splashing a lot of cash about, often making shrewd, cheaper deals to bring players in, so when they opened their wallets to bring Kroldrup in and then showed absolutely no desire to play him baffled many.

    Apparently, in training he didn’t look quite like the player Everton had thought they had bought and then realised he actually couldn’t head the ball, so he was soon sent packing after only one game for the club.

39. Ade Akinbiyi. Wolves to Leicester City. £5.5 Million

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    After breaking his long scoring duck
    After breaking his long scoring duck

    Never looked of Premiership standard and it was amazing Leicester actually paid that much money for him.

    Always looked out of place, clumsy with the ball and ridiculed by supporters, he was lampooned by fans across the country for his desperate misses

38. Diego Forlan. Independiente to Manchester United. £6.9 Million

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    An unknown when Manchester United hijacked his deal from Independiente to Middlesbrough for £6.9 million. Although the United fans took him to their hearts, his spell there was recognised as a flop, only managing to score 17 goals at a ratio of one in every 5.5 games.

    However, he went onto find the grass was greener when he left Manchester, He has  gone on to become one of the best strikers in the world playing for Villarreal and Atletico Madrid and even winning the Golden Ball at the World Cup 2010 for being voted the tournament's best player.

37. Harry Kewell. Leeds United to Liverpool. £5 Million.

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    Kewell’s performances at Leeds had attracted the eyes of most of Europe’s biggest clubs, and after a lot interest, the Aussie international chose to join Liverpool. He was expected to bring the glory days back to Anfield, but he looked a shadow of the player who had terrorized Premiership defences.

    With a serious lack of form and injuries galore, he ended up costing Liverpool nearly £160,000 ($331,000) a game. Liverpool cut their losses and didn’t renew his contract.

36. Michael Owen. Real Madrid to Newcastle United. £16 Million

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    Still looked a quality signing in the beginning of his Newcastle career but unfortunatly, an injury derailed him. His form never regained over four years, and injuries kept on creeping into his game.

    In 2007, Newcastle chairman Freddy Shepherd reacted angrily to reports that Owen could move on to another club at the end of the 2006–07 season, due to a release clause in his contract. A report in The Times newspaper suggested Owen could be available for a smaller fee than what he joined the club for and could be a target for one of the bigger clubs.

    Despite these reports, Shepherd warned Owen "to show some loyalty" and warned him that, "None of the big four clubs want him." However, in a video posted on YouTube, a group of Liverpool fans asked Shepherd if they could re-sign Owen, he responded by saying that he would "carry Owen back to Liverpool" himself.

    He only managed 71 games in four years at the club and then left on a free transfer after refusing a new contract at the club. This upset everyone at the club considering how much they spent on bringing him there and the considerable amount he picked up in wages considering how much he had been injured and his lack of form over the years.

35. Tore Andre Flo. Glasgow Rangers to Sunderland. £6.75 Million

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    Sunderland was after a big name for the new year, so in came Flo as Sunderland’s second highest transfer signing, after enjoying success with Chelsea in the league just a few seasons before everyone knew he could score goals at this level.

    What followed was a very disappointing season with Flo only managing four league goals all year, a couple of falling outs with management and a free transfer at the end of the season as a disappointing Sunderland side got relegated.

34. Hugo Viana. Sporting Lisbon to Newcastle United. £8 Million

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    Cost Newcastle United (a recurring club on these kind of lists) a whopping £8 million and never settled in the North East. Only made 39 games in his two years there mostly as a sub, and he found his previous form after leaving the club.

33. David Bentley. Blackburn Rovers to Tottenham Hotspur. £15 Million

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    Following his excellent form at Blackburn, big things were expected of the right midfielder when he joined Spurs in 2008. And despite one of those five goals coming against rivals Arsenal in the 4-4 draw shortly after moving, he wasn't able to force his way into Harry Redknapp’s side.

    Never looking like the technically gifted player we saw previously, he joined Birmingham on loan in the January transfer window.

32. Karel Poborsky. Slavia Prague to Manchester United. £3.5 Million

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    Signed after a very impressive Euro 96 in England but he had a torrid time at Old Trafford. Struggled to emulate the form he had shown and struggled with the up and coming David Beckham.

    He started just 17 times for United, a game for every month he was at Old Trafford

31. Bruno Cheyrou. Lille to Liverpool. £4.5 Million

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    Signed as “the next Zidane” according to then Liverpool manager Gerrard Houillier. He was wrong. Very wrong!

    Well, he was right about the bald head, but his skills left a lot to be desired. Cheyrou’s welcome was long overstayed when Liverpool offloaded the Frenchman back across the water to the pleasure of the Kopites.

30. Mateja Kezman. PSV to Chelsea. £7.5 Million

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    A free scoring striker in Holland for PSV, his scoring stats matched the likes of Ruud van Nistelrooy, so when he came over to England there was no reason to think he couldn’t carry on where he left off.

    Unluckily for him, he looked like he couldn’t even lace up van Nistelrooy’s boots, failed to live up to his hype as the next big European striker and was let go after one year only managing four goals for the club .

29. Afonso Alves. Heerneveen to Middlesbrough. £12.7 Million

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    Arrived at Middlesbrough with a phenomenal record of having scored 45 goals in 39 league matches in Holland, including seven in one game! He started reasonably for Middlesbrough scoring six in his first 11 games with five of those goals came into two games.

    The next season he was straight-up awful, clearly lacking the stomach for a relegation fight. He only scored four times as Boro went down and decided not to stick around for the fight in the Championship, and Middlesbrough had to cut their losses, which had been a financially bad deal for the club.

28. Jean-Alain Boumsong. Glasgow Rangers to Newcastle United. £8 Million

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    Newcastle paid £8.5 million for the calamitous French man, and all they got back was Bambi on ice. His first season wasn’t too bad, but during his second year no one had faith in him, and it showed.

    Often slipping up and causing too many mistakes, his defensive abilities had lapsed, but he managed to secure a move to Juventus when he left.

27. Titus Bramble. Ipswich Town to Newcastle United. £6 Million

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    Nicknamed Titus Shambles by Toon fans and neutrals alike, his awful howlers and overall clumsiness contributed to his downfall. A lot like Boumsong, he was always on the front line for criticism due to some horrendous performances.

26. Kevin Davies. Southampton to Blackburn Rovers. £7.5 Million.

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    When he was just a young striker at Southampton, Davies was showing promise as a future England striker. After just one year down south in 1998, Blackburn decided to break their transfer record and sign him for £7.5 million, 10 times what Southampton had paid one year earlier, and take a chance on him.

    It backfired.  He scored one goal all year for Rovers, and they got relegated. Davies went back to Southampton the following season in a player swap.

25. Chris Sutton. Blackburn Rovers to Chelsea. £10 Million

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    Chris Sutton scored goals for fun at Norwich City and Blackburn Rovers, so when Chelsea broke their transfer record to bring him to Stamford Bridge, the fans expected more goals to follow. However, after an abysmal debut match where he missed a few easy sitters, his season followed the same patch, only managing one goal in the league all season.

    He was sold to Celtic the following season after one year at Chelsea for £6 million, resulting in a £4 million loss for Chelsea on what they spent a year prior.

24. David Bellion. Sunderland to Manchester United. £3 Million.

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    Dubbed the next Henry due to his lightening quick pace, he quickly alerted the attentions of Manchester United. After a long battle to get him and being accused of "tapping' him up, they finally signed him and had to pay Sunderland £3 million in compensation.

    They shouldn’t have bothered. He could hardly get on the pitch after they realised he wasn’t actually that good, and when he did play, he never looked like he fitted in the top level, not good enough.

23. Kleberson. Atlético Paranaense to Manchester United. £6.5

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    An impressive 2002 World Cup persuaded Manchester United boss Sir Alex Ferguson to splash the cash and bring him to Old Trafford.

    Despite being called the driving force behind Brazil’s World Cup winning team, he never showed any of those qualities during his time at United and left after two seasons making only 20 appearances. Rumours at the time were that he was signed to help Ronaldinho settle in, who was close to a move to Old Trafford.

22. Salif Diao. Sedan to Liverpool. £5 Million

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    A couple of impressive games at the '02 World Cup and Liverpool decided to bring him to their club.  He spent five years there and only played 37 times and went out on loan a couple of times.

    Amazing what a few good games can do for you.

21. Georgios Samaras. Heerneveen to Manchester City. £6 Million

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    Long before Manchester City became the money bags club as they are known today, the £6 million they spent on Samaras was one of their top signings in history.

    The youngster had showed a lot of promise whilst playing in Holland, but once he came to these shores, he proved a flop. It was the days when City didn’t really have money to waste.

20. Sean Dundee. Karlsruhe to Liverpool . £2 Million

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    In 1998, Karlsruhe were relegated from the German top flight and their "well built" striker Sean Dundee only managed three goals during the campaign. This didn’t stop Liverpool in bringing him to England.

    Dundee claimed he was faster than his new strike partner Michael Owen, but he didn’t even look faster than Neil Ruddock. Only managed three substitute appearances and they came near the end of the season. The official Liverpool website once listed him as one of the worst players to ever wear the famous red shirt.

19. Corrado Grabbi. Ternana to Blackburn Rovers. £6.75 Million

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    How the Italians must have laughed into their pasta when Blackburn shelled out so much money on an unknown Italian second division player. And after he made his debut, he still played like a second division player, and it must still baffle Blackburn fans as to what Souness saw in him.

    He lasted three years, 30 games and just two goals

18. Albert Luque. Deportivo La Courna to Newcastle United. £9.5 Million

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    One of the best players in Spain for Deportivo over the years so when Newcastle decided to splash out £9.5 million, it seemed like Newcastle could have bagged themselves an exceptional player.  

    However, when put in the climates of North East England his form dramatically dropped, bringing nothing to the team and injured on too many occasions. Shipped off to Ajax after two years and only 21 games.

17. Marcelino. Mallorca to Newcastle United. £6.7 Million.

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    Regarded as one of Newcastle’s worst ever signings. Spent four years at the club and that was mostly on the treatment table, very rarely making himself available for selection and only managing 17 games in his long stay there.

     At a cost of £6.7 million and his hefty wages, it was a very expensive flop for Newcastle

16. Bosko Balaban. Dinamo Zagreb to Aston Villa. £5.8 Million.

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    The notoriously tight fisted Doug Ellis allowed Villa to sign the expensive Balaban, a free scoring striker in Croatia, but after joining Villa, he hardly got a game. Only made a couple of starts for Villa scoring no goals and sat in the reserves until they let him go out on loan and then cancelled his contract. 

    Joined Bruges after that and started scoring again. A mysterious one.

15. Stéphane Guivarc'h. Auxerre to Newcastle United. £3.5 Million

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    Arrived at St James Park as newly crowned World Cup winner and big things were expected of the striker by the Newcastle faithful. In reality, no one at Newcastle must have really paid attention to France in the '98 World cup because Guivarc’h failed to score and didn’t really play an important part in their winning campaign.

    His non-goal scoring touch didn’t desert him in England either, only managing four games for Newcastle before being shipped off to Glasgow Rangers just a few months later.

    In October 2009, Guivarc'h appeared at No. 1 in a list, compiled by the Daily Mail of the top 50 worst strikers ever to play in the Premiership.

14. Alberto Aquilani. Roma to Liverpool. £17 Million

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    Bought as a very expensive replacement for Xabi Alonso and couldn’t have made a worse attempt at the job. Arrived at Anfield already injured and it seemed to take him months to recover, and when he did, he must of thought why did he bother getting fit.

    The hype following his arrival wasn’t justified, and he looked out of form and out of place and went to Juventus on loan after one season.

13. Adrian Mutu. Parma to Chelsea. £15.8 Million

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    Cost Chelsea £15.8 million but six goals in 27 games was unremarkable. His later drug bust for cocaine use then being sacked by Chelsea was actually far more remarkable.

12. Eric Djemba Djemba. Nantes to Manchester United. £3.5 Million

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    Signed as the long term successor to Roy Keane due to his aggressive and physical approach to the game but sadly, he looked clumsier in the red shirt. Left to Join Aston Villa where he couldn’t get a game and now playing somewhere in Qatar.

    Regarded as one of Ferguson’s worst signings.

11. Massimo Maccarone. Empoli to Middlesbrough. £8.15 Million

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    One of the hottest properties in Italian football and after impressive showings for the under-21’s, a host of clubs wanted him, but it was a real coup when Middlesbrough managed to swoop for him.

    A Teeside transfer record at the time, 18 goals in four years was by no means a rewarding return for Chairman Steve Gibson.

10. Tomas Brolin. Parma to Leeds United. £4.5 Million

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    A star at the '92 European Championships and '94 World Cup, Brolin was recognised as one of the best players in the world at the time.

    Arriving at Leeds already slowly turning to the tubby side, his form and fitness only got worse. Always at odds with the manager, he got sent out on loan at the end of the season, and when returning to the club, he carried on his war with management, and his fitness was now well below the expected standard. 

    Leeds were left with no choice but to terminate his contract, and he is widely regarded by Leeds fans as one of the club's worst ever players, and 2003 a poll by BBC Sport saw him voted by the club's fans as the club's worst player in living memory

9. Winston Bogarde. Barcelona to Chelsea. Free

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    Granted Chelsea may not have paid a fee for Bogarde, but he still drained a lot and lot of money from the club, and this was the days before Roman Abramovich.

    Bogarde was long courted by the blues, and they finally got their man in 2000. After only weeks at the club, the manager, Ranieri, wanted him out but Bogarde claimed no other club would match his lucrative contract that he was being payed at Chelsea.

    He stayed on for four years, earning £40,000 a week refusing to lower his demands to move to another club even though Chelsea made him train with the youth team to try and force him out.

    Of his contract, he said, "Why should I throw €15 million away when it is already mine? At the moment I signed, it was in fact my money, my contract."

    The English press took great fun in ridiculing the selfish Dutchman but his response to his critics was, "This world is about money, so when you are offered those millions you take them. Few people will ever earn so many. I am one of the few fortunate’s who do. I may be one of the worst buys in the history of the Premiership, but I don't care."

8. Francis Jeffers. Everton to Arsenal. £8 Million

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    Coming through the Everton ranks, Jeffers was one of the most promising English players around at the time. Arsene Wenger decided he was the player Arsenal needed as his "fox in the box."

    Out of his depth at Arsenal and in his three seasons there, he only managed 22 games and four goals. His career has never recovered.

7. Serhiy Rebrov. Dinamyo Kyiv £11 Million

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    The other half of the prolific strike partnership with Shevchenko from Dynamo Kyiv came to Tottenham with high expectations from the player himself and the fans. Unfortunately, it didn’t work out, and Rebrov looked a shade of the player who had terrorised European defences with Dynamo.

    Only managed 10 goals in four years at the club then had his contract terminated.

6. Steve Marlet. Lyon to Fulham. £11.5 Million

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    Came to Fulham as their record signing and only managed a ratio of one goal per five games which was derisory. Fulham owner Mohamed Al Fayed also thought that the signing was so abysmal that he took the then Fulham manager Jean Tigana (who bought Marlet) to the high court.

    He claimed Tigana had paid over the odds intentionally (Tigana had ties to Lyon and thought he was taking a cut), and he wanted compensation saying, “I won’t let any crook destroy Fulham.” Al Fayed lost the case and Marlet was shipped out on loan before Fulham cancelled his contract.

5. Marco Boogers. Sparta Rotterdam to West Ham United. £1 Million

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    Two games into his West Ham Career, he earned a red card against Manchester United, and he promptly disappeared afterwards. Officials from the club couldn’t find him until he turned up month later living in a Dutch caravan park.

4. Massimo Taibi. Venezia to Manchester United. £4.5 Million

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    Any goal keeper coming to Manchester United in the period after Schmeichel faced a tough task, but if anyone didn’t look up to the task in hand, then it was this guy.

    Signed a couple of months into the season due to concerns about Mark Bosnich but Taibi only managed to last four games. His first was against Liverpool where even though he flapped for the first Liverpool goal, he was still awarded the Man of the Match. His next were the two home draws against Wimbledon and Southampton where he achieved noriety in the latter due to letting a very slow and tame Le Tissier shot trickle through his legs. 

    His last game came against Chelsea where after making a mistake in the first minute, United went on to lose 5-0. He was never seen at the club again

3. Ali Dia. Dijon to Southampton. Free

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    Definitely the most bizarre transfer of all time! Back in 1996, the then Southampton manager Graeme Souness, received a phone call claiming to be from Liberian international and former FIFA World Player of the Year, George Weah.

    Weah told Souness that Dia was his cousin, had played for Paris Saint-Germain in France and had played 13 times for his country. In reality, none of this was true, and the phone call was made by a fellow university student of Dia's to Souness, suggesting that he should give Dia a chance with the Saints. Nonetheless, Souness was convinced and signed Dia on a one-month contract.

    Dia made his debut a couple of weeks later against Leeds United coming on as a 32-minute substitute. His quality of performance was so bad that he was dragged off the field 21 minutes later.  This Southampton legend only spent a weekend at the club then was never seen by them again.

2. Juan Sebastian Veron. Lazio to Manchester United. £28.1 Million

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    Veron was seen as the man to take Manchester United to the next level and make them perennial Champions League winners when they splashed out a record £28 million, but he just never seemed to adapt to English football. He was great on most of the big European occasions where he could have more time on the ball, but back in England, he never really adapted to the faster side of the game.

    After his two disappointing seasons at United, Chelsea compounded United’s error by signing him for £15 million, and he carried on exactly where he left off. A disappointing two seasons again and he was soon shipped back to Italy. Looked back on as one of the worst signings (twice) made in the league.

1. Andriy Shevchenko. AC Milan to Chelsea. £30 Million

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    Long perused by Chelsea and more importantly Roman Abramovich, it felt like he was the missing piece in the puzzle of Chelsea’s quest to finally win the Champions League. So when they finally got their man for £30 million, the rest of Europe looked on to see just how good Chelsea would become now they had signed the best striker in Europe.

    Sadly it was not to be. Shevchenko’s reputation dropped so fast it wouldn’t have been surprising if no club would take a chance on him again. He scored 173 goals at AC Milan but only managed 22 at Chelsea.

    He left the club to rejoin his first club Dynamo Kiev, via a loan spell back at AC Milan where he failed to score. Lost his feared reputation of one of the best forwards in the game. The most expensive flop of the Premiership era.


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    Sucks to be a Newcastle fan after seeing some of them buys hey? But there you have it! If you think I missed anyone out or don't agree with any of my selections, post a comment!