25 Signings Real Madrid Still Regret Today



Bernabeu Bite - or the fear of the big failure

Real Madrid und der Bernabeu-Bite. Foto: Getty Images
Real Madrid und der Bernabeu-Bite. Foto: Getty Images

Argentinian football legend and “philosopher” Diego Maradona once summed up Real Madrid’s problem as follows: “The problem is that they are all stars at Madrid. You need someone to carry the water to the well.” Not a Maradona of course, but good solid players that know how to carry out their tasks.

Since their foundation in 1902, Real Madrid have transformed themselves from a simple football club into the most powerful football brand in the world, and into a club that has been able to attract the world’s best players again and again. As well as those players that had the desire and potential to make it to the top.

Puskas, Butragueno, Zidane, CR7 were able to show their skills in front of the extremely critical audience in Madrid. They managed to overcome the “Bernabeu Bite”, the fear of failing in front of the notoriously critical fans and the immense pressure to perform at Real Madrid. However, only few of Real’s players managed to live up to the club’s lofty expectations. A long list of big talents and upcoming superstars collapsed under the pressure. Some of them ruined their careers in the process.

The history of failed Real transfers also includes countless failed superstars who made the move to Real in the hopes of becoming megastars. This is especially true of the 21st century and the era of Florentino Perez, the magnetic Spanish entrepreneur, football official and former politician.


The transfers of Mr.Perez that did not work

Jede Saison ein neuer Super-Transfer. Foto: Getty Images
Jede Saison ein neuer Super-Transfer. Foto: Getty Images

Perez is one of the 5 most powerful figures in European football. With a few small interruptions, he has been ruling the Kingdom of Madrid since the summer of 2000.

During this time, managers have come and gone, while Perez has stayed. There is probably no other football club in the world that treats its players and managers as ruthlessly as Real Madrid under Perez. As soon as things aren’t going perfectly, managers and their staff are sent packing and superstar 1 is exchanged for superstar 2. The result of this policy: 13 manager changes in 18 years. Each of the elite managers had their favourite player. However, one manager’s favourite was seldom also the favourite of their successor. As a result, countless players were signed just so that they could spend almost the entire duration of their contract on the bench or on loan at other clubs. We analysed Real’s biggest transfers from the last 30 years and created a ranking. It shows a history of 25 transfers that Real regrets to this day.

The reasons were always different. Either Real had signed the player but things didn’t work out from a sports perspective, or they had to sell the player (for cheap), because things didn’t work out behind the scenes. Some players then went on to flop at the next club, while some – as soon as they escaped Real – went on to celebrate big successes. The spectrum of Real’s worst transfers ranges from massive financial flops to some of the biggest sporting disappointments in history, as well as players from Real’s own youth that failed to make the jump into the first team.

Among them were some teenagers who threw away their careers and simply couldn’t deliver the performances they should have been capable of with a bit more discipline and a bit less ego.

Regret 25 – 21: From a difficult Frenchman to “Maradona’s heir”

25. Nicolas Anelka: "Le Sulk" did not pay off - From Arsenal London for €34.5m | 2009

Anelka und Real Madrid passte einfach nicht. Mandatory Credit: Ross Kinnaird/ALLSPORT
Anelka und Real Madrid passte einfach nicht. Mandatory Credit: Ross Kinnaird/ALLSPORT

Real was in gambling mode when they signed a talented but temperamental young Frenchman. Nickname: ‘Le Sulk' (“The Sulker”).

The gamble did not pay off. Nicolas Anelka only managed to stay with Real for one season. During this time, he scored a meagre 7 goals, but at least they were valuable ones. His first goal happened during the Clasico against Barca and he scored two goals in the Champions League semi-finals against Bayern Munich.

One reason for the low number of goals: Anelka was suspended for 45 days because he had refused to train with the squad. In the aftermath of the suspension, he accused his employer of treating him like a dog.

“Something does not turn around properly in his head,” was Real president Lorenzo Sanz’s analysis, shortly before the enfant terrible was send to Paris St. Germain.

Regret factor for Real Madrid:
High, Anelka was expensive, created turmoil and played badly overall.

What did Real Madrid regret?
The purchase. Anelka was sold for roughly the same amount that Real had paid for him.



Nico Patschinski spielte unter anderem für Union Berlin. Foto: Getty Images

24. Danilo: Misunderstanding from Brazil - From FC Porto for €31.5m | 2015

Danilo konnte sich nicht durchsetzen. Foto: Getty Images
Danilo konnte sich nicht durchsetzen. Foto: Getty Images

Danilo handled his problems in a rather open manner. He had a hard time coping with the attention of the Spanish press that every Real player has to deal with.

“An error, no matter how small, goes viral,” was how he explained his troubles. “A mistake becomes very great even if it is small. But, of course, when you do something good, it is also very great.”

The bad thing was that the Brazilian only rarely managed to do something good while he was playing for Real. During the 2015/16 season, he was on the pitch for every single one of Real’s losses.

In the summer of 2018, Danilo moved to Manchester City. However, the attention he is getting there is only slightly less than when he was in Madrid. At least there is no Dani Carvajal playing at his position in Manchester.

Regret factor for Real Madrid:
Medium, Danilo was expensive.

What did Real Madrid regret?
The purchase. “Stupid English transfer money“ ensured a good sales price.


23. Robert Prosinecki: Bad purchase out of Serbia - From Red Star Belgrade for €15m | 1991

Prosinecki spielte für Barca und Real Madrid . Foto: Getty Images
Prosinecki spielte für Barca und Real Madrid . Foto: Getty Images
When it was all said and done, Robert Prosinecki openly admitted: “My time at Madrid could certainly have been better. But I established myself there at a time when foreign players were limited, and I discovered a different type of football.”

That’s one way of looking at it. The Serb, who was once the best-paid player of his time, will not be remembered for big successes with “Los Blancos”, but rather for injuries and lost titles. Expectations had been high at the start. Prosinecki was one of the most talented football players to ever come out of the Balkans, a gifted midfielder who had just led Red Star Belgrade to victory in the national Champions' Cup. The next step was supposed to be his crowning glory at Real.

Unfortunately, things didn’t work out as planned. The highlight of Prosinecki’s time at Real was probably his goal in the Clasico against Barca. However, even that was tarnished later by his move from Real to Barca in 1995.

Luckily for Real fans, he went on to fail in Catalonia as well.

Regret factor for Real Madrid:
Relatively high, Žuti (“Blondie”) was once the best-paid footballer in the world.

What did Real Madrid regret?
The purchase and sale. The transfer to Oviedo only brought in €3m. Barca later only paid €1.5m.


22. Walter Samuel: "The Wall" didn’t work out - From AS Roma for €25m | 2004

Walter Samuel hatte überall Erfolg, nur bei Real Madrid kam er nicht zurecht. Foto: Getty Images
Walter Samuel hatte überall Erfolg, nur bei Real Madrid kam er nicht zurecht. Foto: Getty Images
Despite a transfer fee of €25m, the signing of Walter Samuel looked like a great deal for Real.

Real were looking for a physically strong centre-back with international experience, and the Argentinian was just that. However, somehow it didn't seem that ‘The Wall' himself had arrived in Spain, but rather a brother or a cousin.

Fabio Capello couldn't really grasp it either. “The fact that he did not make a name for himself at Real Madrid still surprises me,” the star coach said later in an interview. “Perhaps it was the wrong time.”

Or maybe something else wasn't right in Spain. As soon as the Argentinean was back in Italy (2005), he played as well as before – for about 10 years. At Inter Milan he is still a legend today.

Regret factor for Real Madrid:
Very high, Samuel played phenomenal football everywhere, only…

What did Real Madrid regret?
The sale. Samuel was sold to Inter at a great loss. He played brilliantly there for almost 10 years.


21. Javier Saviola: Another of Maradona’s heirs - From FC Barcelona for €0 | 2007

Javier Saviola spielte wenig und wenn dann überwiegend schlecht. Foto: Getty Images
Javier Saviola spielte wenig und wenn dann überwiegend schlecht. Foto: Getty Images
“In retrospect, I would have liked to have played more often,” was Javier Saviola's description of his time in Spain. 

The first few years in Barcelona were not so bad. However, the move to Real was a complete mistake. The former South American Player of the Year never lived up to his expectations as Maradona's heir.

In the end, the signing of Saviola weakened Barcelona but did not strengthen Real. This is a pattern that happens more often than one might think.

“The little rabbit” was unable to hold his own against players like Arjen Robben, Gonzalo Higuain, Raul, Robinho and Ruud van Nistelrooy. After scoring just 5 goals for Real, he was sent to Benfica Lisbon relatively quickly. From there, his career went downhill.

Regret factor for Real Madrid:
Medium, Saviola was a free signing, but had a high salary.

What did Real Madrid regret?
The purchase. It did not strengthen the team, the sale brought €5.0m.




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25 Signings Real Madrid Still Regret Today

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