The 15 Biggest Transfer Fails in Modern Soccer History

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Transfer fee: £19m
From: CSKA Moscow
To: Manchester City
Year: 2008

Signed in July of 2008 for a club record fee at the time, Jo was earmarked as the first major signing of the Mark Hughes era. This is probably why the Mark Hughes era only lasted from 2008-2009. Jo scored just one goal in his debut season for City, a far cry from the 30 he scored in 52 matches for CSKA, and was subsequently sent on loan with Everton. He scored five times for the Toffees during the 2008-09 campaign, but he was sent right back out to Everton upon his brief return to Manchester.

He failed to impress at Everton and was sent on loan with Galatasaray for a season in 2010, where he notched three goals. He would return to City for one more go, but failed to improve upon his one league goal since his record signing. Jo eventually returned to his native Brazil, and Mark Hughes now manages Stoke.

Transfer fee: £21m
From: Shakhtar Donetsk
To: Barcelona
Year: 2009

The first Ukrainian to play for Barcelona, Chygrynskiy inked a five-year deal to play at the center of the Catalan defense. Well, that didn't exactly go according to plan. The former Shakhtar man made just 12 appearances for Barcelona during his lone season in Spain, and failed to live up to the hype of his £21m valuation. A combination of early injury and a general miscalculation of how much pressure was going to be placed on him by the fans and the Spanish media because of his high price tag, ultimately led to Chygrynskiy's move back to Donetsk. For a substantial decrease in price, of course.

Transfer fee: £22.3m
From: Arsenal
To: Real Madrid
Year: 1999

Nicolas Anelka, who's footballing legacy looks on the ropes at the moment, has had a long and traveled career, having an impact at almost every stop along the way. Then there was the 1999-00 season at Real Madrid. A record signing for Los Merengues, Anelka soon fell out of favor with fans, teammates, and manager Vicente del Bosque. We wonder if he could even get a seat at a tapas bar on a Saturday night. Anelka also received a 45-day suspension during his lone season in the Spanish capital for refusing to train.

The Frenchman did show some return on investment by scoring goals in the Champions League semi-final against Bayern, but that would be his last contribution to the club. Two goals in 19 appearances and an unceremonious sending off to Paris Saint-Germain is not what £22.3m should look like.

Transfer fee: £20m
From: Aston Villa
To: Liverpool
Year: 2011

Having impressed during the 2010-11 season with Aston Villa by scoring eight goals in 44 appearances, Stewart Downing became a target for several Premier League clubs, with Liverpool "winning" the race. From the off, Downing was one big disappointment. Despite his £20m price tag, he failed to score a single goal during his first Premier League season with the Reds, and he also became the first player in seven years to miss three consecutive penalty kicks in the Premiership.

For his Liverpool career, Downing scored just three goals in 65 league outings before being cast away in the summer of 2013. Downing now makes a living by not scoring goals for West Ham, as they fight for Premier League survival.

Transfer fee: £21.5m
From: Sao Paulo
To: Real Betis
Year: 1998

The subject of much expectation after he completed his move for a world-record transfer fee at the time, Denilson crashed and burned during his tenure with Real Betis. The Brazilian finished his first season with 35 matches and two goals, and Betis was relegated to the Segunda Division the following season. He would go on loan back to Brazil during the 200-01 season, only to return to Spain for several more years of mediocrity.

When all was said and done, Denilson finished with just 13 goals in 186 league matches for Betis, and would spend the rest of his career bouncing from France to Greece, and everywhere in between.

Transfer fee: £13.4m
From: Newcastle
To: Real Madrid
Year: 2004

A real head-scratcher if there ever was one in the history of football transfers, Jonathan Woodgate's move from Newcastle to the Spanish capital in 2004 baffled many. The oft-injured defender failed to make a single appearance for Real in his first season with the club, and he scored an own-goal and saw yellow twice in his debut against Athletic Bilbao. Talk about a grand entrance. Having made just nine official appearances with Los Blancos, Woodgate never got a foothold in Spain. He subsequently moved back to England with Middlesbrough in 2007. The former England international was also voted the worst signing of the 21st century by readers of the Spanish newspaper Marca, so he'll always have that.

Transfer fee: £17m
From: Roma
To: Liverpool
Year: 2009

Viewed as the talisman of the Roma midfield in 2008, Liverpool and then manager Rafa Benitez saw Alberto Aquilani as a direct replacement for the Madrid-bound Xabi Alonso. Just one goal and 18 league appearances later, Aquilani had made no impact in the midfield, and both he and Benitez were on the same train out of Liverpool. Under new manager Roy Hodgson, the injury-plagued Italian was loaned out to Juventus and Milan in the seasons following his debut. He made substantially more appearances for both sides, and was sold to Fiorentina permanently in 2012.

Liverpool fans will see the £17m signing as the beginning of the end of Rafa's tenure with the club, and the start of a period of instability the club had been mired in up until this current season.

Transfer fee: £21m
From: Manchester City
To: Chelsea
Year: 2005

Brought in by the Special One to help Chelsea regain their 2004 league title, London native Shaun Wright-Phillips found it difficult to get into the first team ahead of players like Arjen Robben, Damien Duff, and Joe Cole. His inconsistent first season at Chelsea cost him a spot with England at the 2006 World Cup, and it took the winger almost 17 months to score his first goal following his transfer from City. Eventually, after scoring a measly four league goals in 81 appearances, Wright-Phillips moved back to Manchester City in the summer of 2008. It looks like sometimes you can't go home.

Transfer fee: £42m
From: Valencia
To: Lazio
Year: 2001

In 2000, Gaizka Mendieta was named European Midfielder of the Season. After the 2001 campaign, Mendieta was named UEFA Best Midfielder of the Year for his performance with Valencia. His squad had just reached the Champions League final for the second consecutive season, losing both times to Real Madrid and Bayern Munich respectively, and Mendieta was in demand. Up stepped Italian side, Lazio, to enlist the services of the Spaniard, and up stepped Mendieta's agent to cash in. His £42m transfer to Italy made him the sixth most expensive player in history at the time, and it was a price tag he simply couldn't live up to.

He failed to replace playmakers Pavel Nedved and Juan Sebastian Veron, and subsequently was sent packing after failing to score in 20 matches.

Transfer fee: £33m
From: Real Madrid
To: Manchester City
Year: 2008

After Robinho's failed contract negotiations at Real Madrid in the summer of 2008, the Brazilian made it public that he was looking for a move to Premier League side Chelsea. Well, he made it to the Prem, but he would don a different shade of blue with Manchester City. After becoming the first major signing of the Abu Dhabi United Group, City's new billionaire owners, Robinho had a solid first season with the club. He finished as City's top scorer with 14 goals, which was also good enough for fourth top scorer in the league. It was all downhill after that, though.

Robinho was plagued by injury in his second season in Manchester, and only featured in 12 games, scoring just one goal for the club. He fell out of favor under new boss Roberto Mancini, and was given his requested transfer back to Brazil in the January 2010 window.

Transfer fee: £28.1m
From: Lazio
To: Manchester United
Year: 2001

He became Britain's most expensive transfer at the time with his move to Old Trafford in 2001, and was described by Sir Alex as one of the best players in the world. Not so fast, Fergie. Veron failed to adapt to the pace of the Premier League, struggling to find his feet on the ball and have a serious impact in the Red Devils midfield. The kicker, though, was the fact that despite seeing his failure with United, Chelsea purchased Veron two years later for £15m. What? Veron once again failed to live up to his value, and a combination of injury and all-around poor play resulted in just 15 appearances for the Blues.

For those keeping score at home, his career of high-priced transfers totals something like £77m. Veron has to be one of the greatest anomalies in sporting history.

Transfer fee: £30.8m
From: AC Milan
To: Chelsea
Year: 2006

A former Ballon d'Or winner, and FIFA World Player of the Year, Shevchenko scored a ridiculous 127 goals in 208 league matches with AC Milan. When he was lured away by Chelsea owner Roman Abramovich, the Ukranian had the expectations of being one of the greatest signings in club history. But life never goes according to script. Shevchenko scored a whopping nine league goals in 48 appearances for Chelsea, and probably left Abramovich redder than his native Russia. So much promise, so little return.

Shevchenko was eventually loaned back to Milan, before completing his career in his native Ukraine with Dynamo Kiev. Maybe he never got over that point-blank miss and failed penalty take against Liverpool in the 2005 Champions League final.

Transfer fee: £35m
From: Newcastle
To: Liverpool
Year: 2011

The most expensive British footballer of all time, Andy Carroll scored 31 league goals in 80 appearances for Newcastle. With Liverpool he never even got out of the starting blocks. Brought in by Kenny Dalglish to lead the line and replace Fernando Torres as the Reds' number nine, Carroll never even came close to living up to the hype in his three years on Merseyside. The Geordie tallied just six goals in 44 league matches for Liverpool, before being thrown out the door upon the arrival of current boss Brendan Rodgers. Carroll, currently with West Ham, is still just 25, but it's hard to see a bright future for the once so highly rated attacker.

Transfer fee: £56m
From: AC Milan
To: Real Madrid
Year: 2009

After netting 70 Serie A goals for Milan between 2003-2009, one of the biggest clubs on the planet in Real Madrid finally came calling to the tune of £56m. Madrid brought the Brazilian in to play along side Cristiano Ronaldo, and battle rivals Barcelona for every trophy available. Neither of those two came to fruition. Kaka failed to find his prolific form from Italy, and looked a shadow of the player that beat out CR for the Ballon d'Or and FIFA World Player of the Year in 2007. Real lost out in La Liga, the Champions League, and the Copa del Rey to rivals Barcelona throughout Kaka's time at the club.

After 23 goals in just 85 La Liga appearances, Kaka expressed his desire to leave the club, and eventually returned to his current club in Milan.

Transfer fee: £50m
From: Liverpool
To: Chelsea
Year: 2011

After netting 65 goals in 102 league appearances for Liverpool between 2007-2011, Fernando Torres became a man in demand in the 2011 January transfer window. Initially the subject of a £40m bid from Carlo Ancelotti's Chelsea, Torres was eventually sold to the London club for £50m just days later. El Nino's move set a British record for most expensive transfer, but the Spaniard has failed to live up to his high price tag. Some of his poor form can be attributed to injury, as well as several changes of the managerial guard.

However, despite his Champions League semifinal winner against Barcelona in 2012, a return of just 19 league goals in 103 matches for the Blues isn't what Roman Abramovich had in mind when he forked over that suitcase full of cash.