Real Madrid's 10 worst transfers of all time

FT Desk
  • FT Desk
  • Updated: 23 Sep 2022 13:09 BST
  • 7 min read
FT Desk Updated: 23 Sep 2022 13:09 BST 7 min read
Eden Hazard, Real Madrid, 2021/22

Crowned European champions a record 14 times, Real Madrid have signed some of the greatest players of all-time over the years, from Alfredo Di Stefano through to Zinedine Zidane and Cristiano Ronaldo. But they haven't always got it right.

They have had to be shrewder in recent seasons, plucking players like Vinicius Junior and Rodrygo straight from from Brazil, with clubs like Manchester City and PSG now backed by oil money and able to price them out of bidding for certain players.

Over the last 25 years, Real have nonetheless managed to build upon their reputation with succession of Hollywood signings, who have each brought their own unique drama to the Santiago Bernabeu - often, but not always, to great acclaim.

But their exorbitant spending has delivered some flop signings to the Santiago Bernabeu too.

Hazard may be the current example of a deal which simply did not work out - but he's not the only one who proved to be an enormous waste of money.

10) Nicolas Anelka - €35m from Arsenal, 1999

Nicolas Anelka was Arsenal’s top goalscorer in the 1998/99 season with 17 Premier League goals and was voted PFA Player of the Year. But he was unable to replicate his form thereafter, and Gunners fans quickly turned on ‘Le Sulk’.

In the summer of 1999 he would sign for Real Madrid for just over €35m, but it would take him five months to score his first goal for the club, his first La Liga strike not coming until the following February.

Nicolas Anelka

Nicolas Anelka

A falling out with head coach Vicente del Bosque soon followed, and even though Anelka would perform well in the latter stages of the Champions League, scoring in both legs of the semi-against Bayern Munich and eventually gaining a winner’s medal, he returned to PSG in the summer of 2000.

9) Elvir Baljic - €26m from Fenerbahce, 1999

Real’s spending spree in the summer of 1999 including splurging €26m on 25-year-old Elvir Baljic from Fenerbahce.

After impressing in Turkey, things went pear-shaped for the Bosnian pretty much immediately after moving to Madrid as he suffered a double cruciate ligament injury before the season even started, putting him out for an extended period of time.

By the time he returned, he was unable to re-find the form he had enjoyed with Fenerbahce, and when John Toshack – the man who brought him to Madrid – was sacked, he fell even more out of favour under his successor Del Bosque.

After a couple of loan deals to Fenerbahce and Rayo Vallecano, Madrid terminated Baljic's contract in 2002.

8) Mariano Diaz - €23m from Lyon, 2018

The signing of Mariano Diaz is one of the strangest in a long history of strange Madrid transfer mistakes.

An La Fabrica academy graduate, Mariano shone for Real Madrid Castilla before making the step up to the first team in 2016. But after quickly realising he wasn’t up to the requisite standard, los Blancos sold him to Lyon in the summer of 2017.

But after one successful year in France, Real bought him back for €23m, which has so far been repaid with a dismal goal return, and he is currently well down the attacking pecking order.

7) Klaas-Jan Huntelaar - €27m from Ajax, 2008

The winter transfer market can be a bit of a minefield and Real found this out when they signed Klaas-Jan Huntelaar from Ajax in January of 2008.

The Dutchman was enjoying a developing reputation as a talented poacher in his time at Ajax and actually performed okay at Real Madrid, scoring eight goals in 20 appearances.

Klaas-Jan Huntelaar

Klaas-Jan Huntelaar

Though he never really had the opportunity to impress, Real Madrid jumped at the chance to cut their losses as after just a half-season in the Spanish capital, and he was moved onto AC Milan in August of 2009.

6) Walter Samuel - €25m from Roma, 2004

Strangely, either side of Walter Samuel’s one unsuccessful season at Real he could be counted among the most dominant centre-backs in the world.

With Roma and Inter the Argentina international enjoyed great success, winning the treble with the latter in 2009/10.

There is no doubt that Samuel flopped at Real, though, and he was unable to translate his defensive abilities to Spain from Italy.

It may simply just be the case that Italian football suited him a lot better, but the Spanish giants had to pay a lot of money to find that out.

5) Royston Drenthe - €14m from Feyenoord, 2007

A big-money addition from Feyenoord, Royston Drenthe signed for Real alongside compatriot Wesley Sneijder. Within three years, one of them had lifted the Champions League and made a very strong claim to win the Ballon d’Or...

That man was not Drenthe.

Instead, he embarked on a stormy five-year relationship with the Spanish club, during which time he had a tumultuous relationship with head coach Bernd Schuster.

After loan spells with Hercules and Everton, he departed with a record of 65 games and four goals in all competitions. It was remarkable that such a workmanlike player survived so long at such an illustrious club.

4) Julien Faubert - Loan from West Ham, 2009

Another of the most bizarre transfers in recent Real history is that of Julian Faubert, who arrived on loan from West Ham.

The Frenchman’s move was a surprise - not least to the players himself - because there was apparently nobody who believed he had the quality to play for Real.

When he moved to Spain, it became apparent why. In his short burst at the club, he managed only a couple of league matches. He was not helped by failing to turn up to training on one occasion because he thought he had the day off.

3) Jonathan Woodgate - €18m from Newcastle, 2004

Woodgate moved to Madrid with a reputation of being one of the most promising young defenders in football - injury permitting. Injury didn't permit, however, and Woodgate failed to make a single appearance in his first 14 months at the club.

Jonathan Woodgate

Jonathan Woodgate

When he did finally play, he produced a debut that has gone down in footballing infamy. Not only did he score a spectacular diving header own goal against Athletic Bilbao, he was later sent off.

Things did not get much better fro there. Woodgate's European debut was a 4-1 defeat by Rosenborg - even if he did score - and just only 11 months after making his debut he was back home in England playing for Middlesbrough.

2) Eden Hazard - €146.1 million from Chelsea, 2019

Hazard’s transfer to Madrid had long been a case of when, not if, he would go, but as it’s turned out the ‘when’ was much more critical than it seemed.

Coming off his most impressive individual season at Chelsea, the then-28-year-old was granted his dream move to los Blancos looking like a sure-fire Galactico.

But arriving overweight for pre-season laid down a marker for a troubled first two seasons. A talisman who often carried his Chelsea team to success is now being brought along for the ride, with injuries and poor discipline to blame.

Since arriving at Real, the once unplayable Belgian has had more injuries than goal contributions. Madrid are now desperate to get rid of him into a fourth successive poor season.

1) Luka Jovic - €60m from Eintracht Frankfurt, 2019

One of the most in-demand strikers in Europe at the time, Luka Jovic was brought in as the long-term replacement to Madrid legend Karim Benzema - for €60m.

The Serbian had posted an almost one-in-two goal record for Eintracht Frankfurt at just 21 years of age, so was undoubtedly deserving of the hype attributed to his name.

Likened to his idol Radamel Falcao, Jovic proved to be an absolute sporting and economic disaster at Madrid, though. He scored just three goals in three seasons for the club and was even loaned back to Frankfurt for the second half of the 2020-21 campaign.

In the summer of 2022, Madrid not only let him leave on a free transfer to Fiorentina, they agreed to pay half of his wages for the following two seasons. They will retain a 50 per cent sell-on clause if Fiorentina decide to sell after those two seasons.

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