25 Expensive Mistakes: The Biggest Transfer Flops In Premier League History
Year: 2009
Transfer Fee: £17 million
Outcome: Two goals in 18 starts, lots of injuries and a loan spell back to Italy
After-life: Now on loan at Juventus, Liverpool fans may never see Aquilani don their shirt again...hopefully
Verdict:
Whatever possessed Liverpool to spend so much money on a creative midfielder who had a history of injuries and could not score goals was beyond most fans.
It was an especially bizarre decision given that Steven Gerrard and Yossi Benayoun already had that need of the team covered and it would have been much more advisable to divert the funds to acquiring a strike partner for Fernando Torres.
Injured before he even arrived, Il Principe will need to sparkle at Juventus if he still harbours hopes of displacing Gerrard in Liverpool's midfield. Bet against it...heavily.
No. 25: Afonso Alves (Middlesbrough)
1 of 26
Analytics
Transfers by position:
Forwards - 15
Midfielders - 9
Defenders - 1
Transfer by club:
Newcastle United - 4
Chelsea, Liverpool, Tottenham Hotspur - 3
Blackburn Rovers, Manchester City, Manchester United - 2
Aston Villa, Fulham, Middlesbrough, Nottingham Forest, Southampton, Sunderland - 1
Transfers by year:
2008 - 5
2001, 2003 - 4
1995, 1999, 2000, 2005, 2006 - 2
1998, 2002 - 1
It is perhaps no surprise that so many players on this list are forwards and so many are imports. Manchester United have proven for many years that, if you spend time, effort and money on your academy, it can pay dividends.
The rise in prominence of the league and the inflated TV revenue which accompanies it has led to some staggering transfer deals which make neither financial nor sporting sense.
This seems to have been aggravated by the influx of foreign managers and owners recently, with 2008 being the worst year for transfer decisions, according to my list.
It is perhaps a slight surprise that I have only included one defender and not any goalkeepers on this list, but it is entertainment and skill which puts bums on seats...and neither position relies on these factors as much as the role of play-maker or goalscorer.
No. 24: Jermaine Pennant (Liverpool)
2 of 26
Year: 2008
Transfer Fee: £32.5 million (+£17 million in wages)
Outcome: 14 goals in 41 league matches
After-life: Still a threat for Brazil and AC Milan
Verdict:
Mercurial. Outrageously gifted. Exciting. Robinho is all of these things.
He is also Brazilian...and Brazilians have had mixed fortunes in the Premier League. Unfortunately for City fans, he flopped...and how!
On a cold night last December at White Hart Lane, the little Brazilian maestro started upfront alongside Carlo Tevez in a crunch match between two clubs on the rise. 90 minutes later, he had been subbed and City had list 3-0.
Sitting among the City fans but as a Spurs supporter, I was initially shocked at the ire and vitriol directed by the away supporters towards Robinho. But it soon became clear that the player had no interest in the club and no passion or fight when the going was tough.
Each of his goals cost the club more than twice what they paid for the services of England's goalkeeper Joe Hart.
At least Shevchenko gave it a go!
No. 23: Helder Postiga (Tottenham Hotspur)
3 of 26
Year: 2008
Transfer Fee: £32.5 million (+£17 million in wages)
Outcome: 14 goals in 41 league matches
After-life: Still a threat for Brazil and AC Milan
Verdict:
Mercurial. Outrageously gifted. Exciting. Robinho is all of these things.
He is also Brazilian - and Brazilians have had mixed fortunes in the Premier League. Unfortunately for City fans, he flopped...and how!
On a cold night last December at White Hart Lane, the little Brazilian maestro started upfront alongside Carlo Tevez in a crunch match between two clubs on the rise. 90 minutes later, he had been subbed and City had list 3-0.
Sitting among the City fans but as a Spurs supporter, I was initially shocked at the ire and vitriol directed by the away supporters towards Robinho. But it soon became clear that the player had no interest in the club and no passion or fight when the going was tough.
Each of his goals cost the club more than twice what they paid for the services of England's goalkeeper Joe Hart.
At least Shevchenko gave it a go!
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No. 22: Winston Bogarde (Chelsea)
4 of 26
Year:2000
Transfer Fee: free (but £11 million in wages)
Outcome: nine league appearances in four years
After-life: A very comfortable retirement and notoriety.
Verdict:
Despite starting his career as a winger, Dutchman Bogarde sealed a dream move to Barcelona on the back of his strong showings in the late 1990s at the heart of a successful Ajax team.
He moved to Chelsea on the advice of compatriot and would-be team-mate for club and country Mario Melchiot, but against the wishes of then Chelsea manager Gianluca Vialli.
New manager Claudio Ranieri took an immediate dislike to the burly defender, but Bogarde would not budge as he felt he would not be as handsomely rewarded elsewhere as he was at Chelsea, which he expressed famously on several occasions: ''This world is about money, so when you are offered those millions, you take them...I may be one of the worst buys in the history of the Premiership, but I don't care'.'
You are, son, but good on you for your honesty (from a Spurs fan, of course!).
No. 21: Andrea Silenzi (Nottingham Forest)
5 of 26
Year: 1995
Transfer Fee: £2 million
Outcome: No goal in 12 league appearances
After-life: Journeyman for unglamorous Italian teams
Verdict:
Silenzi, he of beautiful 1980s mane, signed for Forest to become the first Italian to ever play in the Premier League, after impressing sporadically in Serie A.
However, it soon became apparent that Silenzi would not cut the mustard in England and his contract was reputedly torn up by new manager Dave Bassett after the forward failed to report back from a loan spell in Venice.
No. 20: Jose Kleberson (Manchester United)
6 of 26
Year: 2003
Transfer Fee: £6.5 million
Outcome: 2 goals in 20 league appearances and much embarrassment for nearly untouchable Sir Alex Ferguson
After-life: A spell at Besiktas followed by a renaissance with Brazilian team Flamengo.
Verdict:
The World Cup star with a 15-year-old girlfriend, Manchester United signed Kleberson on the back of a strong showing at the 2002 FIFA World Cup, which led Scolari to describe him as the ''driving'' behind the team's success.
Ferguson would later joke that he thought he signed the wrong Brazilian and quickly shipped the midfielder on to Besiktas for £2 million after he had made predecessor Juan Sebastian Veron look like a decent player.
Fortunately for Premier League, Kleberson ''believes he has unfinished business in the Premier League," accordingly to his agent who was speaking to the press before this year's World Cup. Ferguson will quaking in his boots, I'm sure.
No. 19: Marcelino Elena (Newcastle United)
7 of 26
Year:1999
Transfer Fee: £6.7 million
Outcome: 19 nervous league appearances in a very shaky defence
After-life: 2 years in obscurity at Spanish second division team Polideportivo Ejido, now working as a Premier League commentator for TVE
Verdict:
Marcelino arrived in the hope that he could shore up a Toon defence which had always negated Alan Shearer's goals at the other end of the field, but injury and poor form blighted his career in England.
A player who could have been a success, but fell foul of a demanding league and even more demanding fans.
No. 18: Agustin Delgado (Southampton)
8 of 26
Year: 2001
Transfer Fee: £3.5 million + a hefty medical bill
Outcome: One goal in 11 games in three years!
After-life: Fairly impressive end to his career back in his native South America, albeit playing for teams of dubious quality
Verdict:
Signed by The Saints after scoring freely for Nexaca, Delgado started off his career relatively well and scored a phenomenal nine goals in Ecuado's qualifying campaign for the 2002 FIFA World Cup.
However, he picked up an injury in the same year and, despite Southampton's medical team spending huge amounts of money and man hours on trying to rehabilitate the hefty striker, it was all to no avail.
Delgado left the club after a barrage of criticism from a seething Gordon Strachan, who was furious that the player had been so ungrateful for the support the club gave him and had accused the Ecuadorian of being high-maintenance, leading to one of the great football quotes: ''I've got more important things to think about. I've got a yoghurt to finish by today. That can be my priority rather than Agustin Delgado.'' Oh dear!
No. 17: Kevin Davies (Blackburn Rovers)
9 of 26
Year: 1998
Transfer Fee: £7.5 million
Outcome: One goal in 23 league appearances
After-life: Now a stalwart and fans favourite at Bolton Wanderers, many managers have recently pressed his case as a possible stop-gap for England
Verdict:
Although now an important player at rival club Bolton Wanderers, striker Kevin Davies was an unmitigated disaster at Blackburn Rovers.
He signed for a fee that is still comfortably a club record and scored just once as the team were relegated from the Premier League just a year after it had finished sixth.
Rovers offloaded him in exchange for the equally useless but much less valuable Egil Ostenstad the following season.
No.16: Albert Luque (Newcastle United)
10 of 26
Year: 2005
Transfer Fee: £10.5 million
Outcome: Three goals in 21 league appearances
After-life: Unimpressive spells at Ajax and then Malaga.
Verdict:
After signing Luque from Spanish club Deportivo, Newcastle United fans were excited at the goal threat and supply to Alan Shearer which the pacy Spanish winger would provide.
However, Luque suffered an injury in his second match for the club and could not force his way back into the reckoning. Not a hopeless player by any means, but one of which so much more was expected by the St. James's Park faithful.
No. 15: Hugo Viana (Newcastle United)
11 of 26
Year: 2002
Transfer Fee: £9 million
Outcome: Two goals in 39 league appearances
After-life:A disastrous spell at Valencia, now a winger with Champions League hopefuls Braga
Verdict:
£9 million is a big price tag for any player, let alone for a 19-year-old moving to a new country and a club with a big history and passionate supporters.
Despite winning Young Player of the Year in 2002 in Portugal, Viana never adapted to life in England and was overawed by the experience. Newcastle cut their already substantial losses in agreeing to a £1.5 million transfer with Valencia for the player.
No. 14: Nicolas Medina (Sunderland)
12 of 26
Year: 2008
Transfer Fee: £12.5 million
Outcome: 10 goals in 42 league appearances
After-life: Middle-Eastern ignominy.
Verdict:
'Boro fans were excited but slightly sceptical about the signing in 2008 of Brazilian striker Alves from Dutch club Heerenveen. After all, many a fine striker has come from the land of samba and Alves boasted a phenomenal record of more than one goal a game in the Eredivisie.
Despite a hat-trick in an 8-1 home league victory against Manchester City in the last game of his first season, he managed just four goals through the whole of the following year and his team was relegated.
The North-East club decided to cut its losses and off-loaded Alves to Al-Sadd for £7 million. £550,000 per goal. Enough said.
No. 13: Michael Owen (Newcastle United)
13 of 26
Year: 2006
Transfer Fee: £7 million
Outcome: 3 goals in 55 starts
After-life: Mediocrity in Spain and a new beginning at Stoke City
Verdict:
Pennant signed for Arsenal as a 15 year-old for a record trainee fee of £2 million but only made 12 starts in 5 years for the Gunners, despite a hat-trick on his full league debut.
After various loan spells and a few runs-in with the police, Liverpool decided to gamble on a player who was gifted but volatile.
Despite a promising start to his career to Anfield and support from then manager Rafael Benitez, the afro-haired playboy went off the rails quickly and lost his form so badly that the Merseyside club decided to let him see out his contract and leave on a free.
No. 12: Serhiy Rebrov (Tottenham Hotspur)
14 of 26
Year: 2003
Transfer Fee: £6 million
Outcome:1 goal in 19 matches
After-life: Goals still few and far between both at his 'spiritual home' Porto and now at Sporting
Verdict:
Postiga signed with Spurs on the back of winning the Portuguese league title with Porto as a 21 year-old with a burgeoning reputation as a player in the Teddy Sheringham mould, clever in his positioning and with an eye for goal.
However, he never adapted to the pace and physical rigours of England and, having scored a solitary league goal against Liverpool, moved back to Porto in a part-exchange deal for Pedro Mendes.
No. 11: Corrado Grabbi (Blackburn Rovers)
15 of 26
Year: 2000
Transfer Fee: free (but £11 million in wages)
Outcome: nine league appearances in four years
After-life: A very comfortable retirement and notoriety.
Verdict:
Despite starting his career as a winger, Dutchman Bogarde sealed a dream move to Barcelona on the back of his strong showings in the late 1990s at the heart of a successful Ajax team.
He moved to Chelsea on the advice of compatriot and would-be team-mate for club and country Mario Melchiot, but against the wishes of then Chelsea manager Gianluca Vialli.
New manager Claudio Ranieri took an immediate dislike to the burly defender, but Bogarde would not budge as he felt he would not be as handsomely rewarded elsewhere as he was at Chelsea, which he expressed famously on several occasions: ''This world is about money so when you are offered those millions, you take them...I may be one of the worst buys in the history of the Premiership but I don't care''.
You are, son, but good on you for your honesty (from a Spurs fan, of course!).
No. 10: Chris Sutton (Chelsea)
16 of 26
Year: 1995
Transfer Fee: £2 million
Outcome: No goal in 12 league appearances
After-life: Journeyman for unglamorous Italian teams
Verdict:
Silenzi, he of beautiful 1980s mane, signed for Forest to become the first Italian to ever play in the Premier League, after impressing sporadically in Serie A.
However, it soon became apparent that Silenzi would not cut the mustard in England and his contract was reputedly torn up by new manager Dave Bassett after the forward failed to report back from a loan spell in Venice.
No. 9: Bosko Balaban (Aston Villa)
17 of 26
Year: 2003
Transfer Fee: £6.5 million
Outcome: 2 goals in 20 league appearances and much embarrassment for nearly untouchable Sir Alex Ferguson
After-life: A spell at Besiktas followed by a renaissance with Brazilian team Flamengo.
Verdict:
The World Cup star with a 15 year-old girlfriend, Manchester United signed Kleberson on the back of a strong showing at the 2002 FIFA World Cup, which led Scolari to describe him as the ''driving'' behind the team's success.
Ferguson would later joke that he thought he signed the wrong Brazilian and quickly shipped the midfielder on to Besiktas for £2 million after he had made predecessor Juan Sebastian Veron look like a decent player.
Fortunately for Premier League, Kleberson ''believes he has unfinished business in the Premier League'', accordingly to his agent who was speaking to the press before this year's World Cup. Ferguson will quaking in his boots, I'm sure.
No. 8: Steve Marlet (Fulham)
18 of 26
Year: 2002
Transfer Fee: £9 million
Outcome: Two goals in 39 league appearances
After-life:A disastrous spell at Valencia, now a winger with Champions League hopefuls Braga
Verdict:
£9 million is a big price tag for any player, let alone for a 19 year-old moving to a new country and a club with a big history and passionate supporters.
Despite winning Young Player of the Year in 2002 in Portugal, Viana never adapted to life in England and was overawed by the experience. Newcastle cut their already substantial losses in agreeing to a £1.5 million transfer with Valencia for the player.
No. 7: Robbie Keane (Liverpool)
19 of 26
Year: 2005
Transfer Fee: £16 million
Outcome: 26 goals in 71 games, but never displayed any passion and never got the crowd on his side
After-life: Now a fourth-choice striker for Manchester United
Verdict:
Accused by Freddie Shepherd of lacking loyalty to Newcastle United after he moved to Tyneside from Real Madrid for a club record fee, Owen's career in the North East was overshadowed by problems off the pitch, notably a protracted insurance claim against the F.A. by his club.
Owen also suffered recurring injuries and, despite a hat-trick in one of his first starts for the team and a decent goalscoring record, it was evident that he did not really want to be at the club and was itching for a move back to Liverpool.
An expensive signing who never came close to replacing legend Alan Shearer.
No. 6: David Bentley (Tottenham Hotspur)
20 of 26
Year: 2001
Transfer Fee: £6.75 million
Outcome: Two goals in 30 league starts
After-life: Back to Italy for more misery, now with Swiss ''giants'' Bellinzona
Verdict:
Eye-catching displays for Modena, Ravenna and Ternana attracted the likes of Juventus and AC Milan to Grabbi at the start of last decade.
Mssrs Moggi and Berlusconi will be pleased it was instead Rovers who decided to take an expensive gamble on a player who had still not proven himself at the highest level.
Later complaining of the weather and a cold reception from his team-mates and the management of the Lancashire club, Grabbi proved to be a very expensive and embarrassing signing for a club who longed for the heady heights of its surprise 1995 league triumph.
No. 5: Jo (Manchester City)
21 of 26
Year: 2001
Transfer Fee: £5.8 million
Outcome: Two starts, seven substitute appearances, not a single goal
After-life: Goals galore again playing for Dinamo Zagreb and Club Brugge.
Verdict:
Zagreb has produced many fine footballers, including current Spurs duo Niko Kranjcar and Luka Modric...but Bosko Balaban is certainly not one of them.
Despite scoring many goals both before and after his expensive transfer to Aston Villa in 2001, Balaban was worse than useless during his time in England. His finishing was bad, his touch was bad, his work-rate was bad. In fact, he was so bad that The Times named Balaban as one of the 50 worst footballers to have ever played in the Premier League. Only two starts for Villa really does tell its own story.
No. 4: Juan Sebastian Veron (Manchester United)
22 of 26
Year: 2001 (again!)
Transfer Fee: £11.5 million
Outcome: 11 goals in 54 Premier League starts
After-life: A decent loan spell at Marseilles was followed by woeful performances for Wolfsburg and Lorient. Now enjoying fame and fortune at CM Aubervilliers.
Verdict:
Anyone who could not see that Fulham was wasting a vast amount of money (like so many other clubs at a time when the league was profiting from an increase in interest and TV revenue) must have been blind.
Despite scoring six times in 23 matches for Les Bleus, Marlet never possessed either the pace or quality to unlock decent defences.
So incensed was Fulham owner Mohammed Al Fayed at the player's lack of ability that he took then manager Jean Tigana to court, accusing him of overpaying Lyon for the player and taking a cut of the transfer fee himself. Unbelievably, he lost the court battle.
No. 3: Alberto Alquilani (Liverpool)
23 of 26
Year: 2008
Transfer Fee: £20 million
Outcome: 5 goals in 19 league starts, negligible impact in Europe
After-life: Now back at Tottenham after an excellent loan spell at Celtic, Keane still leads the line for the Republic of Ireland but struggles to make an impact in the Premier League
Verdict:
For a while now, Liverpool have suffered as a result of relying too heavily on two players, Steven Gerrard and Fernando Torres, for goals and quality to win tight games.
Rafael Benitez thought he had seen enough in Keane, scorer of 44 goals for his country and more than 100 Premier League goals, to spend £20 million on bringing him to Anfield and progressing a career which was impressive if interrupted to another level.
However, less than a year later, with Keane struggling to make the desired impact at Liverpool, Benitez decided to sell the Irishman back to Spurs for a big loss, prompting Virgin Trains to poke fun at the situation in one of its promotions: ''A Liverpool to London return faster than Robbie Keane''.
No. 2: Andriy Shevchenko (Chelsea)
24 of 26
Year: 2008
Transfer Fee: £16 million
Outcome: Three goals in 40 league appearances
After-life: Still at the club and fourth-choice behind Niko Kranjcar, Aaron Lennon and Rafael Van der Vaart
Verdict:
Despite excelling for Blackburn Rovers in his last season in the North, the £15 million initial fee which Tottenham chairman Daniel Levy handed Rovers for the services of the England winger surprised everyone.
Undoubtedly a good crosser of the ball, Bentley had still not established himself either as an international or even as one of the better players in the Premier League.
Even though he had some special moments at Spurs, including a stunning 40-yard volley against Arsenal in the league, Bentley has suffered from a lack of confidence in his abilities amongst supporters and incurred the wrath of manager Harry Redknapp for his poor attitude.
No. 1: Robinho (Manchester City)
25 of 26
Year: 2001 (the year of doom!)
Transfer Fee: £28 million
Outcome: 7 goals in 51 starts and much ridicule
After-life: Now at Estudiantes after similarly dire experiences at Chelsea and Internazionale.
Verdict:
When Manchester United manager Sir Alex Ferguson paid a British record £28 million transfer fee to Lazio in 2001 for the Argentine play-maker and Uncle Festa doppelgänger, the world held its breath. This from a manager who had achieved everything but also signed a few duds along the way.
Unsurprisingly, Veron failed to justify this fee. He was careless on the ball, weighed down by a great weight of expectation and outshone by homegrown stars David Beckham, Ryan Giggs and Paul Scholes.
Analysis and Afterthoughts
26 of 26
Year: 2008
Transfer Fee: £16 million
Outcome: One goal in nine starts
After-life: Now back at Manchester City via loan spells at Everton and Galatasaray
Verdict:
Jo was one of the first big-money signings made by Manchester City, the world's richest club, after their takeover by a group of wealthy Arabs.
What led City to make this decision was a record of more than one goals every two games for CSKA Moscow, one of Russia's best teams.
However, with Emmnuel Adebayor, Robinho and Carlos Tevez also arriving at the club, the Brazilian has made no impact so far at Eastlands.
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