Career Killing Transfers – The Biggest Flops in Transfer History


With transfer market valuations being higher than ever, and with young players being snapped up by big clubs very early on in their career, there has never been a better time to look at expensive transfer flops that eventually hindered the player’s career. We will leave out the Andriy Shevchenko’s, Fernando Torres’, and Juan Sebastian Veron’s out of this list to give more players the opportunity to feature!


Andy Carroll

It wouldn’t be a transfer flop article without a mention of Liverpool’s ultimate panic buy Andy Carroll.

After finally succumbing to star striker Fernando Torres’ transfer request late on in January 2011, Liverpool found themselves in desperate need of a big name to replace him.

They chose Andy Carroll. A talented young Newcastle striker who was idolised by the Toon faithful. Liverpool seemed besotted with him, and despite the fact he had only half a season of Premier League experience under his belt they shelled out a club record £30.5 million for him.

This came just a few hours after they signed Luis Suarez for £22 million, a deal which turned out to be quite the bargain.

After his move, he became hampered by a number of injury concerns. He made just 7 appearances for the remainder of the season. He did recover over the summer though, and went on to make 35 Premier League appearances the following season. His goal return wasn’t exactly great though, with the big man netting a measly 4 times.

He was shunned by Brendan Rodgers after this, and sent out on loan to West Ham. He scored 7 times in 24 games for West Ham and eventually signed permanently for £15 million.

His 6 Premier League goals for Liverpool puts the price per goal for Liverpool at around £3 million, taking into account the £15 million deficit in recouped transfer fees.

He is still injury stricken, but has begun to reconstruct his career after a disastrous few years at Liverpool, and he will probably never reach the heights that his potential promised.

David Bentley

Remember him? The right sided midfielder was touted as the next David Beckham when he exploded onto the Premier League scene for Blackburn Rovers back in 2006.

He scored a hat trick against Manchester United, and scored some stunning goals throughout the season.

He scored 15 goals and laid on 26 assists in 2 Premier League seasons for Blackburn, and was seen as one of the hottest young talents in the country.

After Mark Hughes left to join Manchester City, David Bentley asked to leave. Tottenham Hotspur paid around £15 million for his services.

After a less than impressive debut season for Spurs, he started falling down the pecking order, also falling out of favour with the England management team. Eventually, he was loaned out to a number of relegation threatened clubs over a period of 3 years. He didn’t impress there either, failing to score a single league goal in 3 years.

He was released by Tottenham after his 6 year contract had run it’s course, and no other club came in for his services. After a year without a club, David Bentley announced an early retirement at the age of 29 years old.

He now runs a restaurant in Marbella. Quite the fall from grace.


Signed as a long term successor to the ageing Paul Scholes, Anderson was touted as the next big midfielder in the world.

Porto had already shelled out £7 million for the youngster who had been impressing for Gremio. He continued to show his potential in the Portuguese league.

This led to Sir Alex Ferguson shelling out a massive £25 million on the young midfielder. He showed glimpses of his class in the first few seasons at Manchester United, but struggled with the physical demands of the Premier League.

Eventually, injury and unfitness took over, and he fell out of favour with the management team. He was put up for sale last summer, and eventually Fiorentina agreed to take him on loan. He failed to impress there as well, and has now returned to his native Brazil to try and find his feet again.


Denilson was touted as the next Ballon D’Or winner when he moved to Real Betis in 1998 for a world record fee of £21.5 million.

This is a big fee for a 21 year old who has only played in the Brazilian Serie A, and indeed it proved too much for the flamboyant left winger to deal with.

He failed to perform at Real Betis, showing glimpses of quality but ultimately unable to save his new team from relegation.

The world record signing did help his team achieve promotion back to La Liga, but was then relegated to the bench as he continued underperforming.

After being sold to Bordeaux in 2005 he then went on a mercurial prowl of 7 different clubs in his final 5 playing years, and retired in 2010 having never taken the world by storm.

Julio Baptista

Julio Baptista signed for Sevilla in 2003 for a bargain price of £1.75 million. He instantly made a name for himself at the Spanish club, scoring 24 goals in 36 appearances in his first season in Europe. All this playing from attacking midfield as well.

Despite interest from a number of bigger clubs, Baptista stayed at Sevilla for another year, scoring another 25 goals to prove he wasn’t just a one season pony.

Real Madrid couldn’t hold off any longer, and shelled out a reasonable £14 million for the 24 year old. It was here that he proved to be a two season pony. He was thrown out on the left wing for Real Madrid, and only managed a return of 9 goals in 45 appearances in his first season in the capital.

Arsenal took him off Real Madrid’s hands on loan after his disappointing season, but only managed to score 3 Premier League goals for the North London club.

He returned to Real Madrid the next season, and they persevered with him. He was often utilised in his preferred central attacking midfield in his second spell with the Madrid giants, but still failed to find the heights he found at Sevilla.

After another disappointing season, AS Roma signed him for around £6 million, failing to perform in the Serie A as well. He spent two and a half seasons in Rome, and then moved to Malaga for just over £1 million.

He started brightly at Malaga, scoring 9 goals in his 11 La Liga appearances, but then injury problems took over. He made only 18 appearances over the next 2 years for Malaga before his contract was terminated.

He now resides back in his home country of Brazil, playing for Cruzeiro.


Of course, there is always an inherent risk when signing a potentially world class player. Cristiano Ronaldo was seen as selfish, childish, and lacking an end product in his early years at Manchester United. Gareth Bale went over 20 games for Spurs without being on the winning side as a left back. With the inconsistencies players show in their early careers, it’s no wonder that there are a number of big money flops when the rewards for a success are so high.

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