Move: AC Milan to Real Madrid. // Transfer sum: $92 million. // In 2009, Kaka was already a Champions League and World Cup winner with AC Milan and Brazil, respectively. By the time he moved to Real Madrid in May of that year, he was ready to prove himself at arguably the biggest club in world soccer. The fee reflected his ability at the time and how well he was thought of in the game. The fee was certainly not unreasonable, though thinking back about his time at the Santiago Bernabeu, he was unfortunate to have his appearances limited by injury. Yet, for the fee that was paid, his undoubted pedigree and the subpar performances means he makes this list.
Action Images / ReutersSERGIO PEREZ
Move: Liverpool to Chelsea. // Transfer sum: $67 million. // Torres transferred to Chelsea in January 2011, making him a new British transfer record. Since then, the Spaniard was under the guidance of several different managers and played with a constantly transitional frontline. Torres has scored 20 goals in 110 games for Chelsea following his move from Anfield. That works out at around a goal every five games and roughly $3.3 million for each time he scored. For such a high price tag, and considering his brilliant performances for Liverpool previously, there's no reason not to include "El Niño" on this list.
Action Images / ReutersSERGIO PEREZ
Move: Newcastle to Liverpool. // Transfer sum: $60 million. // Carroll’s move to Liverpool from Newcastle was one of the most unexpected transfer deadline day signings in recent years. The hefty move from St. James’ Park happened in January 2011 and was a direct result of Liverpool's panic buying after losing prolific striker Fernando Torres. Carroll was unfortunate to have a price tag that was unrealistic and inflated at the time. He had always been a target for Liverpool, but not at that price and they never played to his strengths. He managed 11 goals in 58 games for the Reds before they made a $35 million loss, selling him to West Ham United for $25 million.
Action ImagesEd Sykes
Move: AC Milan to Chelsea. // Transfer sum: $53 million. // Shevchenko is a legend in the Ukraine and rightly so, the international was a consistent performer for club and country before a game changing move. In May 2006, Shevchenko secured a blockbuster moved from AC Milan to Chelsea. Reportedly the move was the idea of Blues owner Roman Abramovich and not manager Jose Mourinho, who didn’t seem keen to give the Ukrainian a pivotal role. He managed 9 goals in 48 Premier League games for the club before departing for Milan on loan the following season, and eventually rejoining Dynamo Kyiv.
Action ImagesTony O'Brien
Move: Real Madrid to Manchester City. // Transfer sum: $55.4 million // Robinho’s move to Manchester City coincided with the Citizens getting taken over by an Arab Investment Group on the last day of the 2008 summer transfer window. Apparently, Robinho preferred a move to Chelsea, as evidenced when asked by a reporter at the time of his move. He finished his first season as top scorer for City with 14 goals. The second season was not as good as the Brazilian fell down the pecking order after injury and poor form. Considering his transfer fee, Robinho remains one of the highest paid flops of all-time.
Action ImagesPaul Thomas
Move: Arsenal to Real Madrid. // Transfer sum: $37.5 million. // "Le Sulk," as Anelka is known in some circles of the French media, has always scored goals wherever he has been -- without a doubt Real Madrid was his least clinical spell. Arsenal received the incredible sum for the French international after they gave in to Madrid’s approaches. Anelka started well at Real, with instant success. However, he soon fell out with fans, colleagues and most notably Vincente del Bosque. He will be sulking all the way onto our list of flops.
Action Images / ReutersDesmond Boylan
Juan Sebastian Veron
Move: Lazio to Manchester United. // Transfer sum: $48 million move. // "The Little Witch" had a fairly unproductive time at Manchester United and if it wasn’t for a Premier League crown, it would have been a resounding failure. The Argentine midfielder managed seven in 51 appearances after his move from Italian football and injury kept him from making any more appearances after securing a deal to Stamford Bridge.
Getty ImagesJeff Gross
Move: Sao Paulo to Real Betis. // Transfer sum: $36.6 million // Moving for a world-record transfer fee in 1998, the Brazilian wasn't cut out for life at the Seville club despite making 186 appearances in total. However, Denilson's impact was never felt at Betis and the club were relegated in 2000 with the player returning to Flamengo on loan before eventually being shipped off to Bordeaux.
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Moves: Coventry City to Internazionale & Tottenham to Liverpool. // Transfer sums: $22 million (by Inter) & $32.4 million fee (Liverpool). // Since moving to Major League Soccer, Keane has been a major success, scoring a goal every two games he plays -- though he hasn’t always had it his way. Two deals stick in the mind when it comes to Keane, who has had some serious money spent on him over the years. Firstly, Keane moved from Coventry City to Internazionale, where he made 14 appearances and scored three goals. After a spell with Leeds and a fantastic time at Tottenham, he moved to Liverpool on a four-year contract. Keane was to only spend seven months at Anfield before moving back to Spurs for similar money. This clear distinction makes Keane a top candidate in our list.
Action ImagesJason Cairnduff
Move: Newcastle United to Real Madrid. // Transfer sum: $23 million // In 2007, Woodgate was voted the worst signing of the 21st century by Spain's leading sports daily, Marca. Woodgate got 37.11% of the votes -- a pretty damning verdict we think you’ll agree. Woodgate swapped the River Tyne for the glamor of Madrid in 2004 and impressed in the time he was on the pitch. After a nightmare debut where he scored an own-goal and got sent off, he managed to establish himself in the team with some impressive performances. Woodgate was injured for much of his three years at Madrid, and now finds himself plying his trade for Middlesborough after his career took a nosedive. Poor business.
Action Images / ReutersSergio Perez
Move: Roma to Liverpool. // Transfer sums: $28.9 million. // Brought in as a replacement for Xabi Alonso after the Spaniard's move to Real Madrid, Aquilani had big shoes to fill. Unfortunately, the midfielder wasn't well suited to life in the defensive midfield role coach Rafael Benitez envisaged for him and struggled to cope in the Premier League. A loan move back to Italy hoped to reignite Aquilani but solid displays for Juventus and then AC Milan couldn't be repeated for Liverpool who eventually let him go in 2012 to Fiorentina for a measly fee.