The 20 Biggest Flops in Chelsea History

Joe Krishnan@joekrishnanContributor IOctober 8, 2013

The 20 Biggest Flops in Chelsea History

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    The headline is fairly self-explanatory, and any fan of English football will be aware that Chelsea has had the biggest turnover of player transfers over the past 10 years or so.

    Some have came, saw and conquered, while others have come to see their careers fade and die. It's a part of football, but the latter seems to happen far too often at Stamford Bridge for it to be purely just a coincidence.

    Fernando Torres still has time to prove he is not a flop and has made a decent start to the season, with two goals to his name so far. But the £50 million striker knows the pressure is on to deliver, although he is exempt from this list.

    Come with us and see if you agree with our choices. If not, please let us know using the comments box at the bottom.

Slavisa Jokanovic

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    You know those figures in football who are better managers than footballers? The obvious figures, being Arsene Wenger, Jose Mourinho and Sir Alex Ferguson, spring to mind, of course.

    But let us not forget that Slavisa Jokanovic, widely regarded as one of the worst signings in Chelsea's history, appears to fall into that category as well.

    The midfielder represented the former Republic of Yugoslavia and made his name in football with Tenerife and Deportivo La Coruna before a £1.7 million switch to Claudio Ranieri's Chelsea side in 2000.

    However, just 39 appearances and a string of poor showings followed before leaving Stamford Bridge at the age of 34. His lack of pace and dynamism in the midfield frustrated the supporters, and Jokanovic is obviously keen to make amends for a poor end to his career.

    He went into coaching after his retirement in 2004 and led Partizan and Muanythong United to their domestic titles in Serbia and Thailand, respectively, before taking over at Levski Sofia this summer. 

    And while his management career may have taken a positive step forward, the negative memories of his existence at Chelsea will forever remain.

Chris Sutton

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    The only positive reflection Chelsea fans will have on Chris Sutton is the fact they managed to get a decent return on the £10 million the club spent on him in 1999.

    After scoring 50 goals in 131 games for Blackburn Rovers, the Blues opted to take advantage of that club's relegation by snatching their top player, albeit for a club-record fee at the time.

    But Sutton never got going in West London and managed just one goal in 28 Premier League games: a strike in the 5-0 thumping of Manchester United.

    Two goals in a European tie with Skonto Riga followed, but ultimately his career looked to be doomed at Chelsea, with the one-cap England striker heading toward the exit.

    A £6 million switch to Celtic followed in the summer, and after an impressive spell with the Scottish club scoring 63 goals in 130 games, he moved back to the Premier League with Aston Villa

    A short spell with Birmingham then followed, and now the 40-year-old plies his trade for nonleague side Wroxham. 

Slobodan Rajkovic

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    Chelsea paid £3.8 million to bring what they thought was one of the best defensive talents in world football to Stamford Bridge. But a nightmare unraveled after Slobodan Rajkovic failed to get a work permit.

    A loan to Eredivisie giants PSV Eindhoven came in the 2007-08 season that was followed by a two-year spell at FC Twente, but when Rajkovic finally could get his work permit, he spent another season out on loan with Vitesse.

    Eventually, the Serb became disillusioned with the club and negotiated a release from his contract, which saw the 24-year-old join up with Frank Arnesen, the technical director at Chelsea, at his new club, Hamburg.

    He left without making a single competitive appearance for the club in the four years he was associated with them. But with several hefty investments in youngsters since then, Chelsea clearly see Rajkovic as an isolated mistake as they continue to recruit the world's best young talent. 

Andriy Shevchenko

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    Before Fernando Torres, there was an arrival at Stamford Bridge who was a pretty big deal.

    But the uproar about Andriy Shevchenko's £30 million switch from AC Milan to Chelsea was based solely around whether Jose Mourinho wanted to sign the Ukrainian legend. The answer to that question appeared to be "no."

    The media criticised Roman Abramovich for bringing an ageing striker (30) in for such a large amount of money without his manager's consent. Others said the Russian was the owner of the club, and as it was his money, he could do what he wanted with it.

    But unfortunately, the underlying reason for Shevchenko's demise was that he was no longer the player he used to be.

    A paltry return of nine league goals in 48 appearances capped a miserable two-year spell at the club, and after returning on loan to Milan, he went back to Dynamo Kiev, the club where it all began back in 1994. But even in spite of Torres' struggle, this was the first major flop and it's one Chelsea fans aren't likely to forget in a hurry.

Adrian Mutu

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    Adrian Mutu represents the small minority of players who cannot handle the fame that comes with football. Had he not tarnished his career with the shameful incidents off the pitch, the Romanian could have been a magnificent player.

    Chelsea recognised his talent in 2003 and paid £15.8 million to acquire Mutu from Italian side Parma after Roman Abramovich's takeover. He made a decent start to his career, netting four goals in three games but things turned sour when Jose Mourinho took charge.

    Mutu was accused of feigning an injury while on international duty and, as a result, publicly criticised Mourinho. It then emerged that the striker had been suffering from depression, before failing a drug test after testing positive for cocaine.

    Banned for seven months by the English FA, Chelsea made the decision to sack the forward, claiming he breached his contract. Mutu served his ban but joined Juventus on a free transfer, prompting Chelsea to seek damages and the Blues were awarded £16 million in damages to be paid by Mutu. That decision was taken in 2006, Mutu is still appealing.

    In the meantime, the striker has endured a frantic career, spending most of his career in Italy with Fiorentina and Cesena before arriving at French club Ajaccio.

    The Chelsea supporters will always be wondering what might have been had his drugs shame not ruined his career at Stamford Bridge, but should he ever return, there is bound to be no love lost between the two. 

Jiri Jarosik

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    It's perhaps one of the strangest signings made by Jose Mourinho. If you were to ask him why he signed Jiri Jarosik in 2005, chances are Mourinho would struggle to come up with a reason why.

    Of course, he wasn't a bad player, and when he signed, he was a 27-year-old Czech Republic international. But compared to the likes of Claude Makelele, Michael Essien and Frank Lampard, he wasn't in the same category.

    Just 14 appearances followed after a £3 million switch from CSKA Moscow (ah, you've spotted the link now) and he was loaned out to Birmingham for the remainder of the 2005-06 season, where he gained some more regular playing time.

    However, Chelsea decided to sell him to Celtic in 2006 after the West Midlands club refused to make the transfer permanent and the Blues had to once again let loose a seemingly average player from their books.

Steve Sidwell

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    Signed on a free transfer from Reading after leaving on a Bosman, Steve Sidwell was not quite the No. 9 that Chelsea were looking for.

    Of course, what is meant by that is that the club gave Sidwell the actual No. 9 shirt, perhaps thinking it would bring him some luck. It didn't.

    Just 15 appearances under Jose Mourinho and then Avram Grant followed before a £5 million switch to Aston Villa. Considering the disappointment of his short spell at the club and that he cost nothing, a profit as large as that would have been welcomed by both the management and the fans.

    Now at West London rivals Fulham, Blues fans are grateful he turns up with the visitors when Fulham come to Stamford Bridge nowadays.

Alexei Smertin

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    So it's not exactly in the same bracket as Slavisa Jokanovic, but there was a feeling that the signing of Alexei Smertin from CSKA Moscow was one forced through by Roman Abramovich.

    This was reflected by Claudio Ranieri's decision to loan him out just months after a £3.5 million switch from the Russian club, and despite spending three years on the payroll, Smertin managed just 16 games for the Blues.

    He was used as a bit-part player in Jose Mourinho's 2004-05 title-winning squad and collected a winner's medal after accumulating more appearances than required.

    But that was about as pleasurable as his career got before moving back to Russia with Dinamo Moscow, with the former Russia captain retiring in 2007.

Shaun Wright-Phillips

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    There was so much excitement when Chelsea managed to sign an England international, especially when it was speedy winger Shaun Wright-Phillips.

    The £21 million fee may have proved excessive, but the midfielder became an instant favourite with the fans under Jose Mourinho.

    Sadly, it seemed Wright-Phillips found it difficult to adapt to the way Chelsea played. It's not a lack of action that affected himhe made 124 appearances overall for the Blues during his three-year spellbut just seemed to lack that danger he possessed at Manchester City.

    He eventually moved back to his former employers in 2008 after Mourinho's departure for a third of the fee Chelsea paid, and the 31-year-old now plies his trade at QPR, having not made an appearance for England since 2010. 

    The only positive moment for the little speed merchant is that he scored the only goal as the R's secured a shock 1-0 win over Chelsea last season, perhaps feeling some sense of karma.

    A career that promised so much without actually delivering anything, Wright-Phillips will look back with some regrets though.

Scott Parker

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    Like Wright-Phillips, Chelsea supporters were hoping that when the club signed young English midfielder Scott Parker in January 2004, he would form an unstoppable British contigent at the club with John Terry and Frank Lampard.

    However, a number of factors impacted Parker's time at Chelsea, including the arrival of Jose Mourinho just months after he signed for the Blues.

    The Portuguese boss came in and signed Tiago, who was preferred to Parker in the centre of midfield alongside Lampard and Claude Makelele. It left the former Charlton utility man out in the cold, but still managed to pick up a winner's medal after making 15 appearances. 

    Parker knew he was on his way out though, and Newcastle's £5.5 million was good enough to let Chelsea release him from his duties. A successful spell in the North East led him back to London with West Ham, Spurs and now Fulham.

    More was expected from Parker's 18-month spell with the three-time Premier League winners, and there will always be a sense of what might have been for the England midfielder.

Juan Sebastian Veron

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    After the Argentinian midfielder failed miserably to make an impression at Manchester United following a £28 million move, Chelsea decided to gamble and sign him for £14 million, half what their rivals paid Lazio.

    But it wasn't just in Manchester where the veteran struggled to perform. Just seven league appearances followed after a dream start to his career with a goal in the 2-1 win over Liverpool, it was evident Veron could not deal with the pace of the Premier League.

    He suffered from a string of injuries and, when he finally returned, found it difficult to regain his form or confidence. Jose Mourinho was clearly not prepared to give him a chance to impress and sent Veron on loan to Inter Milan for two years before he left on a free transfer to return to Argentina with Estudiantes.

    He currently plays and is the sporting director for the club, despite being 38 years of age. Nobody could deny his obvious ability, but even Veron must look back his time in England as a waste of his career.

Yuri Zhirkov

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    Another mysterious Russian signing from Chelsea saw Yuri Zhirkov sign for the Blues in a whopping £18 million deal from CSKA Moscow in 2009. 

    Whether it was Carlo Ancelotti or Roman Abramovich who made the final decision on this transfer doesn't matter. What is important is the contribution Zhirkov made to the club wasn't a lot.

    In fact, his only goal came against Spartak Moscow in the Champions League. In fairness to the Russia international, it was a stunning strike. But the full-back was never more than a fringe player with Ashley Cole in the form of his life.

    Injuries hampered him including a recurring ankle problem, and it wasn't too long before Chelsea decided to cut their losses just two years later, selling him to oil-rich Anzhi Makhachkala, although the West London club managed to recuperate around £13 million.

    It may be harsh to call Zhirkov a flop, but for the money paid and the below-par showings that came with it, he's unlikely to live long in the memory of Chelsea supporters. 

Khalid Boulahrouz

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    Another player cursed with the No. 9 shirt when he really shouldn't have had it, Khalid Boulahrouz has endured a strange career to date.

    His form at Hamburg had earned him a lucrative move to Chelsea, and Jose Mourinho hailed the Dutchman's versatility in giving him options along the back line. 

    But a serious knee injury blighted his career at Stamford Bridge and the former RKC Waalwijk defender never regained top form. He was loaned out to Sevilla for the 2007-08 season, when again he struggled to adapt, making just six appearances.

    Chelsea sold the defender to Stuttgart after his loan finished for a fee of £5 million, where he spent four years before joining Sporting Lisbon and finally current club Brondby. But if Boulahrouz is honest, the Der Kannibale will feel he should be with a better side at 31 years of age.

Mateja Kezman

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    The list of Jose Mourinho signings appears to be growing, doesn't it?

    But perhaps Mateja Kezman was the most disappointing of them all when you consider what a fine goalscorer he was during his time at PSV Eindhoven.

    The Serbian forward, like Steve Sidwell, Khalid Boulahrouz and Fernando Torres, wore the dreaded No. 9 shirt vacated by Jimmy Floyd Hasselbaink. And after arriving in a £5 million deal from the Dutch giants, expectations were high.

    His total of 105 goals in 122 games was simply remarkable, but perhaps the pressure got to him. Kezman managed just four goals in 25 Premier League appearances before leaving for Atletico Madrid for the same fee he arrived for.

    Now retired, Kezman still reflects on Chelsea as "the best time of his career," per Sky Sports, but others might not look back with such nostalgia.

Winston Bogarde

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    Rather much like in the case of Florent Malouda, Winston Bogarde angered the supporters of Chelsea after the Dutch international chose to prioritise money over his career.

    Though you can hardly blame him. Chelsea decided to hand the defender, who was 29 at the time, a four-year deal worth £40,000 a week when he signed from Barcelona back in 2000. Thirteen years ago, that was a lot of money for a footballer to earn.

    Within weeks of his arrival, the club were looking to offload Bogarde, but instead of looking for a new club, the former AC Milan man decided to sit on his lucrative contract until it expired.

    He made just nine league appearances during those four long years. Nobody could deny his work rate, refusing to miss a training session, but ultimately his decision to sit on the bench and earn his astronomical wages meant he is not welcomed back at Stamford Bridge these days.

Enrique De Lucas

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    Another odd find from Claudio Ranieri, Enrique "Quique" De Lucas was one of the rare pre-Abramovich flops after arriving at Stamford Bridge in 2003.

    He signed on a free transfer after four years at Espanyol, and despite featuring regularly for Chelsea in his debut season, he never really got off the mark in the Premier League.

    He scored just one goal overall—a wonderful chip against Viking in the UEFA Cup—and his disappointing form saw him move on to join Alaves, where he spent four wonderful years of his career.

    Now 35 and at Hercules in the Segunda Division, De Lucas may look back and feel he should have done more with his time in England, although the Spaniard has achieved many great things in his home country.

Robert Fleck

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    Former Chelsea owner Ken Bates signed Fleck for £2.1 million in 1992.
    Former Chelsea owner Ken Bates signed Fleck for £2.1 million in 1992.Harry How/Getty Images

    It hardly made sense for Chelsea to break their transfer record to sign a striker with a record like Robert Fleck.

    The Norwich striker had only hit 39 goals in 143 games for the Canaries before signing for Chelsea in 1992. 

    But the four-time Scotland international experienced a downturn in fortunes, scoring just three times in 40 league games for the Blues, and was loaned to Bolton and Bristol City before rejoining Norwich.

    He remains a cult hero around the grounds to this day, with fans singing his name to the Beatles' hit "Yellow Submarine," but that's about as far as his place in history goes.

    Bates has been critical of successor Roman Abramovich's lavish spending in the past but with signings like Fleck, he certainly has no leg to stand on.

Pierluigi Casiraghi

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    After the club had shelled out £5.8 million to sign Italy star Pierluigi Casiraghi from Lazio, the move was hailed as a masterstroke.

    But just 10 games into his career, with one goal to his name, Casiraghi's life would change forever. In the game against Liverpool, the forward collided with keeper Shaka Hislop, sustaining an unrepairable cruciate ligament injury.

    Despite 10 operations to save his career, Casiraghi was forced to retire aged 31, much to the dismay of Chelsea fans.

    However, he went onto become Italy's Under-21 manager between 2006 and 2010, so his contribution to the game is no just limited to his playing career.

    But it's another case of how cruel injuries can be, and considering the investment, Chelsea were devastated that the move didn't work out.

Asier Del Horno

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    After the club spent £8 million on the Spanish left-back, Asier del Horno looked to have settled into Chelsea reasonably well in 2005.

    He made 25 league appearances in his debut season, pushing Wayne Bridge onto the bench and performed to a decent standard.

    However, trouble came about when he clashed with a young Lionel Messi in the Champions League clash with Barcelona. Del Horno was sent off and Jose Mourinho then sought another left-back, eventually bringing in Ashley Cole in 2006.

    Del Horno was sent to Valencia for £5 million and gradually made his way around Spain with former club Athletic Bilbao and Levante.

    The 31-year-old is currently a free agent, but without a club in over a year, it may be a good time for Del Horno to call it a day.

Tal Ben-Haim

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    Finally, we reach the last stop of the flops: Tal Ben Haim, the much-travelled Israeli defender who has caused a fair bit of controversy in his time.

    A great spell at Bolton saw him earn a lucrative free transfer to Chelsea in 2007, but after Jose Mourinho was sacked, Ben Haim criticised his replacement Avram Grant, which led to him being fined two weeks' wages.

    He made just 13 appearances for the Blues, before Man City then swooped in the season after he joined with a £5 million deal, giving the Blues a nice profit from the transfer.

    Ill-fated periods at Sunderland, Portsmouth and West Ham eventually led to him moving to Belgium with Standard Liege.

    But it's fair to say that after signing for his 10th club in six years, Ben Haim's sense of loyalty is nonexistent. The Chelsea fans would certainly agree that the feeling is mutual.