Top 10 Most Expensive Transfer Flops

Transfers. Arguably the most important part of the modern game. More and more money is being pumped into the game as a result of new TV deals, sponsorships and other sources of income. This has meant transfer fees have skyrocketed over the last few years, resulting in even more money being spent by clubs all over the world.

Not every big money signing works out at their new club as the pressure of a huge transfer fee can heavily impact their performances. We take a look at the top ten most expensive transfer flops…

#10 – Angel Di Maria – Real Madrid to Manchester United – £63m

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Ex-Real Madrid winger, Angel Di Maria, became Manchester United’s record signing in 2014 when he swapped Madrid for Manchester in a move worth £63m. Di Maria was a real signing of intent as Louis van Gaal aimed to put Manchester United back on top of the Premier League.

However, the Argentina international could not settle in the Premier League despite making a strong start to his career at Old Trafford. He ended his United career with just four goals in 32 appearances and struggled to displace Ashley Young in the starting eleven towards the end of the season. He was sold to PSG just one summer later where he has rediscovered his best form and has broken Ligue 1 assists records with the Parisians.

#9 – Robbie Keane – Tottenham to Liverpool – £20m

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Robbie Keane arrived at Anfield with a reputation as one of the Premier League’s most clinical finishers. The Irish international was identified by Rafael Benitez as the perfect partner to Fernando Torres in the Liverpool attack and splashed almost £20m to bring him to Merseyside.

Keane went 11 games without scoring in a red shirt before finally opening his account for his boyhood side in a Champions League game against PSV. His goalscoring troubles continued until November when he finally scored his first Premier League goal for the club. He lasted until January before being resold to Tottenham.

#8 – Jonathan Woodgate – Newcastle to Real Madrid – £13m

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Former England international, Jonathan Woodgate, had established himself as a top centre-back in the Premier League following spells with Leeds and Newcastle. He was a fan favourite on Tyneside but the club could not refuse when Real Madrid came calling and a £13m offer was accepted.

Woodgate endured a torrid time in Spain as his spell in the Spanish capital was blighted with injuries. He made no appearances in his first year at the club as he was injured when the transfer was completed. The 36-year-old finally made his debut in 2005 and scored an own-goal as well as being sent off later in the game. He made just 14 appearances before being sold to Middlesbrough and is widely regarded as the worst transfer in Real Madrid’s history.

#7 – Robinho – Real Madrid to Manchester City – £33m

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Following the club’s takeover by billionaire Sheikh Mansour, Manchester City broke the British transfer record in September 2008 on deadline day when the Citizens completed the £33m transfer of Robinho. The Brazilian had established himself as a key player for Real Madrid but had seemed destined to join Chelsea before his switch to City.

Despite a strong start to his career in Manchester, where he scored 15 goals in his first season, Robinho struggled for fitness and form in his second year. He made just ten appearances and scored just one goal against Scunthorpe before being sold to AC Milan following a loan spell with former club Santos.

#6 – Dmytro Chygrynskiy – Shakhtar Donetsk to Barcelona – £21m

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Pep Guardiola is widely regarded as the best manager in world football and has had plenty of success in the transfer market. However, his move for Ukrainian defender, Dmytro Chygrynskiy, went down as one of the worst signings in Barcelona history.

The Catalans paid just over £20m for his services after he helped Shakhtar Donetsk reach the final of the UEFA Cup. Despite signing a five-year-contract, Chygrynskiy was notorious for a number of high-profile errors which meant he was sold back to Shakhtar after just one season in Spain.

#5 – Andriy Shevchenko – AC Milan to Chelsea – £30m

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Ukrainian legend, Andriy Shevchenko, was another forward who arrived in England with a huge reputation. The striker had blossomed into one of the most feared strikers in the world during his time with AC Milan where he received the Ballon d’Or in 2004. The 39-year-old ended his Milan career with 175 goals in 296 games before he moved to Chelsea for over £30m.

His form at Stamford Bridge was inconsistent as he struggled to adapt to the physicality and pace of the Premier League. Shevchenko scored just 14 goals in 51 games in his debut season and the arrival of Luiz Felipe Scolari deemed the striker surplus to requirements after just two years in England. He moved to Milan on loan before returning to former club Dynamo Kyiv.

#4 – Kaka – AC Milan to Real Madrid – £55m

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Real Madrid smashed the world transfer record in 2009 when club president, Florentino Perez, announced the £55m capture of AC Milan’s Kaka. The Brazilian playmaker had built a reputation as one of the best in the world and was named FIFA World Player of the Year in 2007 as well as receiving the coveted Ballon d’Or.

Kaka’s arrival was perhaps overshadowed by the signing of Cristiano Ronaldo the same year as Kaka struggled for form with Los Blancos. His moments of magic were few and far between during his stint in the Spanish capital. Four years later, Kaka left to rejoin AC Milan on a free transfer following only 29 goals in 120 appearances. The Brazilian now plays in the MLS with Orlando City.

#3 – Juan Sebastian Veron – Lazio to Manchester United – £28m

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Manchester United announced the signing of Juan Sebastian Veron in the summer of 2001 and had seemingly clinched the signature of one of the world’s best midfielders. Veron’s form in Italy had prompted Sir Alex Ferguson to spend £28m to lure the Argentine to Old Trafford.

However, Veron could not acclimatise to the Premier League as he had less time and less space on the ball. The pressure of the huge transfer fee may have also affected Veron who did improve in his second season in England. His transfer was seen as hugely disappointing and he soon joined Chelsea for £15m in 2003.

#2 – Fernando Torres – Liverpool to Chelsea – £50m

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Former Atletico Madrid striker Torres set the Premier League alight when he joined Liverpool in 2007 for just over £20m. Torres was a defender’s nightmare, a quick and intelligent forward with lethal finishing abilities. His form may have slowed towards the end of his Liverpool career under Roy Hodgson but Chelsea were still willing to pay £50m for the Spaniard. After a defeat to former club Liverpool on his Chelsea debut, things quickly went from bad to worse for the 32-year-old.

He finally scored his first goal for the Blues against West Ham after 903 minutes without a goal; which was also his only goal of the season. Torres did improve in his second season but his goal return did not merit that of a £50m striker as the former Spanish international bagged just 11 goals in 49 appearances. Poor form continued until Chelsea finally cut their losses and allowed the forward to join AC Milan on loan before the Italians made the move permanent. Torres is now back with former club Atletico Madrid where he has rediscovered his goalscoring touch.

#1 – Andy Carroll – Newcastle to Liverpool – £35m

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Eager to replace the outgoing Torres, Kenny Dalglish decided to spend £35m on Newcastle striker Andy Carroll. Despite only half a season in the Premier League, the Reds moved for Carroll to partner new signing Luis Suarez in Liverpool’s attack. Carroll had made a huge impact on Tyneside but many people questioned the huge transfer fee.

He arrived at the club struggling for fitness but eventually scored his first two goals for his new club in spectacular fashion against Manchester City at Anfield. Carroll was unable to find the net for the rest of the season. The England international’s goalscoring woes continued into his second season where he seemed tactically inept to Liverpool’s fast-paced system. He later joined West Ham on loan before the Hammers made the move permanent for a reported £20m.

The £35m is viewed by the majority of people as a colossal waste of money but as a Liverpool fan; as Jamie Carragher once said, the winning goal against Everton at Wembley in the semi-final of the FA Cup was “worth £35m in itself.”

Who do you think was the biggest transfer flop of all-time? Comment below!

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