The biggest football transfer gambles that failed to pay off

As another UK football season gets underway the headlines have been filled with a flurry of last-minute transfer activity. As ever, fans will have seen some good business, some crazy deals and some rather… questionable signings.

But then, that’s what sport is about isn’t it? Just as we like a flutter in the casino, a football manager seems to be rather fond of a gamble here or there too – particularly when it comes to handing over the big bucks for a player. In reality, no one knows just how a new signing will turn out, which is why there’s been some disasters throughout the years.

In honour of those football managers that have been prepared to take a punt, we look at the biggest transfer gambles that have been just a little disappointing.

Fernando Torres: Liverpool to Chelsea £50m

Football gambles torress

In the summer of 2007, Fernando Torres was snapped up by Liverpool looking for their next star to lead their line. They certainly got it, as Torres turned out to be a goal scoring machine for the reds. Four years, 145 games and a staggering 81 goals later, and Torres was at the peak of his powers when the Russian owned wealth of Chelsea came knocking in January 2011.

£50 million was the agreed fee, and Chelsea were rubbing their hands believing they had just snapped up a guaranteed Premier League goal machine.

However, for whatever reason, Torres struggled to live up to the price tag and was loaned back to Atletico Madrid after scoring a total of 45 times in 175 games.

Jonathan Woodgate: Newcastle to Real Madrid £13.4m

Jonathan Woodgate

Perhaps not the highest fee in our list, but £13.4 million for a defender in 2004 was a decent amount and Woodgate’s move to the Bernabeu certainly raised a few eyebrows.

Nobody could doubt Woodgate’s talent, a solid, consistent performer for Leeds United in his early career saw him move to Newcastle after Leeds’s fall from grace, but it was Woodgate’s debut for the Blancos that will live long in the memory of every football fan.

During his first league match for Real, he managed to score an own goal and get himself sent off late in the game. Injury setbacks limited his playing time for Real Madrid and he ended up leaving after having played just 14 games.

Andy Carroll: Newcastle to Liverpool £35m

andy carroll

Once again Newcastle appear to be pretty good at selling a player for big money at just the right time. Carroll had performed brilliantly for the club in the season that they won promotion back to the Premier League and was on fire in the first half of the 2010/11 season with 11 goals in his first 19 games.

That prompted Liverpool to come in and make a huge offer of £35m which the Magpies accepted. Injury delayed his Liverpool debut but he went on to make 9 league appearances scoring twice in the second half of the campaign.

Nothing disastrous there but it was the following season when Liverpool realised they had clearly paid over the odds. Just four league goals in 35 league games had the Liverpool faithful questioning the decision with numerous injuries playing their part.

Afonso Alves: Heerenveen to Middlesbrough £12m

alves middlesborough
Photo: Grieg Cowie/Action Images

Brazilian, Alves took the Dutch top flight by storm after scoring a staggering 45 goals in just 39 appearance in 18 months. That record earned him a move to the UK’s Premier League with Middlesbrough.

The fee was £12 million, which was a lot of money for the club but then, with that record how could he fail to be a hit in the Premier League? Unfortunately, 18 months in the northeast yielded just 10 goals in 42 appearances and a disappointing return of investment.

Robinho: Real Madrid to Manchester City £32.5m

Robinho man city

In the summer of 2008, Brazilian Robinho signed for Manchester City for an eye watering £32.5m although it later transpired he had actually wanted to go to and play his football for Chelsea.

This may well have led to the reason why he quickly fell down the pecking order at City, despite finishing his first season as top scorer for the club with 14 goals.

Despite this, injury and his large wages led to him being labelled a flop after failing to score for the club again.

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