Across the largest soccer leagues in Europe, billions of dollars are spent each and every year on transfers.
From the English Premier League to La Liga, clubs fork out tens of millions on big-name signings when the transfer windows open up.
Whether it is to add more firepower to their attacks, a little creativity in midfield, or to bolster a leaky defense, clubs are always on the lookout for players to take them to the next level.
At times, clubs recruit these stars in the hope that they will keep them from being relegated to a lower division.
With so much money in soccer, many transfers are driven by the greed of players’ agents. Some superstar agents engineer multi-million dollar transfers in order to make millions in fees for themselves.
That’s just the nature of the beast in soccer.
But when the “superstars” turn out to be duds, there is no way to look for a refund.
Players that were signed off the back of big performances in the FIFA World Cup or an impressive one-season performance can often look severely out of their depth when it comes to performing for their new clubs.
In other words, they flop. Sometimes, in spectacularly bad fashion.
How We Ranked The Flops
There are a few select factors that came into the equation when compiling this list.
First and foremost, a large transfer fee is usually in line with the main reason why a player who underperforms would be given that tag.
The expectation a club has on a record-breaking transfer is going to be considerable, after all, so a $50 million signing who underperforms is going to sting a lot more than a $500,000 transfer.
Second, a player’s reputation/perceived ability also determines how badly they will be received, should they consistently underperform.
If a club has signed a star striker who has prolifically hit the back of the net for their former clubs and can’t hit the side of a Boeing 747 with an umbrella, questions must be asked.
Last of all, just how badly that player performed in line with both their transfer and their abilities is also something that is taken into account.
With that, let’s take a look at the first player on the list.
5. Jo (Brazil)
- CSKA Moscow to Manchester City
- Transfer Fee – £19 million
These days, Manchester City are regarded as arguably the most complete team in world soccer.
Featuring players such as Sergio Aguero, Kevin De Bruyne, David Silva and a whole host of other world class stars, they are a team that has made winning a habit.
Prior to signing CSKA’s star striker Jo in 2008, the club had finished 14th in the EPL. Things were certainly not as rosy for the blue side of Manchester.
Needless to say, investment in the club led to greater expectations and a real hope that City could begin to find a little more success in domestic competitions.
Paying a club record fee of £19 million for the Brazilian – who had netted 30 goals with CSKA the year prior – was seen as a statement of intent, and a coup for City.
Arriving to the club following the 2008 Olympics in China, Jo was expected to lift the team to greater heights.
His goal scoring record was certainly something that preceded him, so fans couldn’t wait to catch a glimpse of what was meant to be their star striker.
After a few games, those same fans couldn’t wait to cover their eyes every time he touched the ball.
What Went Wrong?
Man City fans would not have been blamed for wanting a DNA test on the player in order to prove it was the same guy who had lit up the scoring charts in Russia a year earlier.
Jo’s only league goal for the club came against Portsmouth. Other than that, his biggest contribution was two assists (one against Portsmouth and another against Southampton).
By the following season, Jo was loaned to Everton in a bid to capture the form that saw him signed for City in the first place. The Brazilian would upset Everton by flying home without permission.
A subsequent loan to Turkish side Galatasaray failed to offer any hope of the striker offering City anything in the future.
Despite this, Man City gave him one last chance at redemption.
Jo’s efforts in his final season at the club returned just 3 goals in 23 appearances.
4. Jonathan Woodgate (England)
- Newcastle United to Real Madrid
- Transfer Fee – $24.5 million
When looking back through some of the more improbable transfer signings in the history of soccer, Jonathan Woodgate to Real Madrid has to rank up there with the oddest.
Woodgate was far from the type of player that the Galacticos would usually be in the market for. He wasn’t particularly flashy, nor did he command the level of attention off the pitch that would have sold shirts.
The England defender was, well, solid.
Well, solid when he was playing and not spending the majority of his time on the physio’s table.
Woodgate was renowned for his uncanny ability to get injured – a lot. That said, Madrid clearly saw something that they liked and forked out $24.5 million for his services to Newcastle United.
Whether they believed the sunny Spanish clime would have been good for his health is unknown, but either way, they soon found out that Woodgate was made of glass.
What Went Wrong?
Oh, nothing really.
Well, that is unless you consider not making a single appearance for the team in his first season a good thing.
Marid quickly got frustrated with Woodgate but had to deal with the fact that he was attracted to the sidelines.
Following his first season – where he might as well have gone home and watched games from his couch in England – Woodgate returned from injury to work his way into the team.
Season two was hardly much better.
In Woodgate’s debut, he scored an own goal and was sent off after picking up two yellow cards.
Woodgate would make a grand total of 9 league appearances in two seasons with Madrid before moving to Newcastle’s rivals, Middlesbrough in 2006.
A poll conducted via Spanish soccer magazine Marca voted Woodgate the worst signing of the 21st century.
3. Fernando Torres (Spain)
- Liverpool to Chelsea
- Transfer Fee – $82 million
When Liverpool’s star striker Fernando Torres moved to club rivals Chelsea in 2011, fans of the reds were gutted.
Some saw it coming, while others did not want to believe that the Spaniard would leave Anfield for another club in the league, let alone to play at Stamford Bridge.
Regardless, Liverpool dried their eyes momentarily with $82 million before splashing it out on a player they hoped would eventually become a legend for club and country (more on this later).
Torres came with an incredible reputation and Chelsea fans were nothing short of ecstatic with the signing.
Although the former Athletico Madrid star was the most expensive signing in British history at the time, he was expected to hit the ground running and take Chelsea – the league champions – even higher.
After a few games, Torres started showing worrying signs, however.
The goals that many had thought would be raining down were nowhere to be seen. In fact, it would take Torres a total of 14 games – 903 minutes in a Chelsea shirt – before he would find the back of the net.
What Went Wrong?
To most, it appeared that Torres was struggling with the tag of the most expensive player in British history.
To others, he had simply lost more and more confidence in his abilities for every game that he failed to score in.
That first goal was the only time he hit the back of the net in his first season, which was frustrating to the Chelsea board who had paid so much money on account of his 81 goals in 142 appearances for Liverpool.
In 2011/12, Torres scored just 6 goals in 32 league appearances for Chelsea.
The following two seasons at the club saw him make the scoresheet a combined 13 times in 64 league appearances.
Torres’ career simply went downhill the day that he signed for Chelsea.
While Liverpool fans gloated at the striker’s poor performances for the Londoners, they would have to deal with a major flop of their own in Torres’ place.
2. Andy Carroll (England)
- Newcastle United to Liverpool
- Transfer Fee – $57.4 million
Arguably the floppiest of flops in Premier League history, floppy-haired striker Andy Carroll would become synonymous with profligacy in front of goal.
Following Torres’ move to Chelsea, club-legend Kenny Dalglish brought the powerful striker down from Newcastle United for a whopping $57.4 million.
Forking out most of the $82 million he received for the Spaniard on Carroll was a major risk, and it would be one that would all but end his reputation as an astute manager.
Carroll had a solid record at Newcastle, notching up a very respectable 31 goals in 80 games with the Magpies. That said, 17 of those goals came in The Championship, England’s second-tier competition.
Carroll made 7 appearances in his first season for the club, scoring two goals.
In his first full season (2011/12), Carroll hit the net a paltry 4 times in 35 league games.
Hardly the stats of a superstar in the making.
What Went Wrong?
The general consensus is that Caroll was a panic buy that was nowhere near as talented as the price tag suggested.
If anything, he was still in the developmental stages of his career at Newcastle and was thrown into the deep end at Liverpool.
Although it became clear that he wasn’t going to cut the mustard at Anfield, Carroll was eventually bought by West Ham for just under 50% of what Liverpool paid for him.
While he has struggled with injuries over the past few years, he has regularly featured for West Ham when fit.
Soccer fans can now clearly see that the former Newcastle man was never going to be a prolific goalscorer at Merseyside. More than anything, he will probably be remembered as the biggest flop in English soccer.
To date, the last time that he has scored more than 9 goals in a league campaign came with Newcastle back in 2010/11.
1. Denilson (Brazil)
- Sao Paolo to Real Betis
- Transfer Fee – $37 million
To Betis, it must have seemed like the most foolproof plan of all time.
Dish out a world transfer record fee for the impressive World Cup finalist Denilson and simply sit back and watch as he single handedly transforms the fortunes of the club.
Dear Betis – what were you thinking?
Yes, Denilson had an excellent tournament in France that year, standing out in a Brazil team that showed flashes of brilliance despite losing 3-0 to the hosts.
However, the winger was never going to be the type of player that would score tons of goals and any scout worth their salt should have brought that to the club’s attention.
Prior to joining Betis, Denilson had scored just four goals in 50 appearances for Sao Paolo.
Although flashy and capable of individual brilliance, he was going to need top-class players around him in order to perform to his highest capabilities, surely?
In terms of mistakes, Betis will forever be haunted by the signing of Denilson.
Although paying an astronomical amount of money for him at the time, they would be relegated in 2000.
Denilson managed to score just 13 times in 186 appearances for Betis, either side of a loan move to Flamengo in 2000.
Evidently, Denilson’s excellent showing at the World Cup was enough for the club to rush for his services.
Denilson was probably not as good as those few games at France ’98 suggested, given his lack of influence for Betis.
Although he joined in 1998, he did actually stick around with the club until 2005 when he was sold to Bordeaux (with four years remaining on his contract).
Naturally, the club wanted to give their record signing as many chances as they could for him to prove himself and show the type of form that he had done in the World Cup.
I mean, there is blind faith and there is being just blind.
For Betis, they will always be associated to the biggest flop in soccer transfer history.
I feel kind of bad for them, too.
Throughout the past few decades, there have been a number of transfer flops that come to mind.
Although the 5 above are the worst of all time, they are not alone in signing for a club and failing to deliver.
One thing you might have noticed when it comes to the 5 candidates we have covered already is that 3 of them were signed by English Premier League clubs.
For whatever reason, the EPL seems to have a track record of signing duds, mostly given the extortionate transfer fees that are frequently paid for players of questionable abilities.
Regardless, life will continue the way it always had and these same clubs will likely find themselves falling for the flop trap again sometime in the future.
If and when that does happen, I’ll be sure to update this list accordingly.