Five Of The Biggest Chelsea Flops Of All Time

By : UNILAD Football |


luis Five Of The Biggest Chelsea Flops Of All TimeESPN

Filipe Luis seems to be closing in on an exit from Chelsea – or a return to Atletico Madrid as he probably prefers to call it – but no matter how the left back looks at it, his first and only season at Chelsea was an unprecedented disaster.

He failed to convince Jose Mourinho that he was worth a place in the first team, could not displace Cesar Azpilicueta – a right back by trade – and spent more time using Instagram and teaching Diego Costa English than he did on the field.

Chelsea might not be too fussed given they’re not losing a huge amount of cash on the player, but Luis has managed to go from one of the best defenders in Europe to an outcast – and he is not the only player to have joined a club and failed in spectacular style.

With that in mind, here are five Chelsea flops who make Fernando Torres look like a world class buy. Torres, in case you’re wondering, didn’t make the cut purely because of his goal at the Camp Nou. Gary Neville’s reaction alone was worth £50 million.

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Winston Bogarde

What a joker. The defender will go down in history as one of the biggest contract rebels the game has seen, and managed to sit on his backside and extort the Blues for a massive £40,000 per week. This was despite not even playing for the first team in the final three years of a deal he refused to walk away from.

To add insult to injury for the Blues, he also pocketed bonuses when the club did well, and decided it was fine to fly in from Holland on a daily basis for training with the reserves in his final year at the club.


Not a good move by the player, but an even worse one for Chelsea, who seemed to think offering a player in the latter stages of his career a huge deal when they were about to sack the manager who wanted him was a golden idea.

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Yuri Zhirkov

Another left back who Chelsea have seen flop, and one who could have been replaced by Asier Del Horno in the countdown. Quite what it is with Chelsea and utter failures on the left hand side of their defence remains to be seen, but it’s worth noting that Ashley Cole and Cesar Azpilicueta have been two of the best in the league over the last decade – with Cole probably taking the award for best left back of all time.

That of course makes it hard for players to break through, and that is exactly what Chelsea’s next left back, who looks like being Baba Rahman, will find – although it helps if you actually keep the ball when you come on the field and are more interested in defending than bombing up the pitch.

Zhirkov was a prime example of Roman Abramovich buying a player he liked as a person for big money and seeing it cost his club dearly.

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Andriy Shevchenko

Speaking of… we have Ukrainian forward Sheva, who at £30 million was an unprecedented disaster. In fact, you can probably still find Chelsea fans who think it is Sheva, and not Torres, who was their all time biggest failure in the transfer market, and it’s hard to disagree with them.

Not only was Sheva effectively finished at the 2006 World Cup – something that was clear for everyone watching to see – but he went on to join Chelsea against the wishes of Jose Mourinho and was the main factor in the breakdown between Mourinho and the Chelsea owner, which of course led to Mourinho leaving the club.

Despite a debut goal against Liverpool, the ‘forward’ only found the net nine times in 48 games after that and had most Chelsea fans preparing for an opposition goal kick each time he touched the ball.

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Adrian Mutu


Where to begin with the party boy who also liked a cheeky line of cocaine on a casual weekday evening? Mutu was axed by new boss Mourinho, who was unimpressed with his off the field lifestyle, not to mention the fact that Mutu tested positive for coke in his system, and it was £15.8 million down the drain.

He was one of the first signings newly rich Chelsea made back in 2003, so while it can’t be blamed on Jose Mourinho, it is certainly one for the Blues to look back on and try not to repeat.

Sadly for their fans, the club went on to buy more than a couple of flops when trying to add to their forward line, and 6 goals in 26 games for Mutu isn’t even that bad considering some of their other disasters. Radamel Falcao is yet to take to the field after all.

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Shaun Wright-Phillips

Chelsea love signing wingers for more money than they’re actually worth, but Serious Waste of Pennies has to be one of the worst. £21 million isn’t a small fee, even a decade on from the 2005 signing, and only four goals in 82 appearances is really not good enough.

Wright-Phillips failed to get into either Jose Mourinho or Avram Grant’s side and was eventually sold for a paltry £9 million, and has seen his career tank. Chelsea might be blamed here for not giving young players a chance, but let’s be honest. Wright-Phillips was simply not good enough to play for one of the best clubs in England, let alone the world, no matter what his dad will tell you.

A mistake you’d like to think Chelsea wouldn’t repeat, but the Blues never seem to learn their lesson and this time next year, Juan Cuadrado will probably usurp Wright-Phillips in the list.