10 WORST Real Madrid signings since 1990s ranked – Kaka 2nd, Jonathan Woodgate 4th
Real Madrid are arguably the biggest club in the world, but even the best and the richest make mistakes.
While the history of Los Blancos is replete with world-class footballers and legends, the Spanish and European giants have also made some ridiculous blunders when it comes to making signings, especially for big money.
Below are the 10 worst signings that Madrid have made.
It is important to note that for the purpose of this list, we have included players that the Spanish club signed since the 1990s.
10. Nuri Sahin (2011-2014)
Nuri Sahin was one of the cornerstones of the Jurgen Klopp-led Borussia Dortmund team that sensationally beat Bayer Leverkusen and Bayern Munich to the Bundesliga title in 2011.
The former Turkey international midfielder endured a tough debut season at Estadio Bernabeu, as he had injury problems and competition for a place in Jose Mourinho’s team.
Now 38 and the manager of İstanbul Basaksehir, Sahin had a loan spell at Liverpool and Borussia Dortmund in 2012/13, with the deal being made permanent thereafter.
9. Walter Samuel (2004-2005)
Walter Samuel enjoyed a highly successful career, as the former Argentina international central defender won Serie A five times and the Champions League once with Inter Milan.
During his spell at AS Roma, the defender became the Italian champions in 2001. Even with FC Basel, Samuel won the Swiss Super League title twice in a row in 2015 and 2016.
However, it was at Real Madrid that Samuel flopped. Los Blancos paid Roma £15m to add Samuel to their Galacticos team, but after a season in which he failed to make an impact, he was moved on.
8. Nicolas Anelka (1999-2000)
Real Madrid thought that they were getting the next big thing in European football when they splashed the cash and signed Nicolas Anelka from Arsenal in the summer of 1999 for £23.5million.
The former France international striker was 20 at the time and had won the Premier League and the FA Cup with Arsenal in 1998.
While Anelka was part of the Madrid team that won the Champions League in 2000, Los Blancos decided to move him on after a season in which he missed training, was fined and suspended, and complained that then manager Vicente Del Bosque’s tactics did not suit him.
7. Thomas Gravesen (2005-2006)
It was the sign of the times. (Then and now) president Florentino Perez was watching his Galaticos project collapse and thought that signing Thomas Gravesen from Everton would reverse the course.
Los Blancos paid £2.5million to the Premier League club for the former Denmark international midfielder, who looked like a fish out of water surrounded by superstars such as Ronaldo, Luis Figo, David Beckham and Zinedine Zidane.
Leaving an also-ran Premier League team such as Everton for the world’s biggest club is a step that not many can take and be successful, and Gravesen was not among them.
In February 2025, Brazil legend Ronaldo said that Gravesen was his worst ever teammate at Madrid.
Ronaldo said when asked to name his worst teammate: “There are a lot of them. There was one at Real Madrid who was a joke… Gravesen. He was a Danish midfielder. He was a really cool guy, good guy. A little while ago he won a $50 million poker tournament or something. But in football he was very bad, he scored and he beat the hell out of people.”
6. Julien Faubert (2009)
Julien Faubert must have thought that it was a joke when it was put to him that Real Madrid wanted to sign him from West Ham United in 2009.
The former France and Martinique international right-back/right-winger was struggling to get into the first team at the Hammers at the time and ended up joining Los Blancos on loan in January 2009.
It was a disaster of a spell personally for Faubert at Estadio Bernabeu, as he could make only two appearances for the Spanish and European powerhouse.
During his time at Madrid, Faubert hit the headlines for missing training after mistakenly thinking he had the day off and claimed that he was “bored” on the bench during a game against Villarreal.
5. Royston Drenthe (2007-2012)
In fairness to Real Madrid, Royston Drenthe did show a lot of promise at Feyenoord, and it would have been hard for anyone at the Spanish club to envisage that the Dutchman would be a flop at Estadio Bernabeu.
Drenthe scored a stunning goal on his debut for Madrid, kept Marcelo out of the team initially and won LaLiga in his debut season for Madrid, but it went all downhill thereafter.
After loan spells at Hercules and Everton, Drenthe ended up leaving Madrid for good in 2012, joining FC Spartak Vladikavkaz in Russia.
4. Jonathan Woodgate (2004-2007)
Real Madrid paid Newcastle United £13.4million to sign Jonathan Woodgate in the summer of 2004, and from the outset, it looked doomed.
There were concerns that the defender would not pass his medical, having been sidelined with a thigh injury since April 2004.
Woodgate did not play a single game for Los Blancos in his first season at Estadio Bernabeu, eventually making his debut for the Spanish and European giants against Athletic Bilbao in September 2023.
Then 25, Woodgate scored a spectacular own goal when he headed the ball past Madrid goalkeeper Iker Casillas while trying to clear a shot from Joseba Etxeberria and was sent off on 65 minutes after picking up a second yellow card.
After a loan spell at Middlesbrough in 2006/07, Woodgate joined the English club on a permanent deal, and that was the end of his Madrid story. Woodgate made just 14 appearances in a Madrid shirt.
3. Luka Jovic (2019-2022)
Luka Jovic is a classic case of why a top club should not sign a player because of just one good season.
Real Madrid paid Eintracht Frankfurt £52.4million for Jovic in the summer of 2019 and has high hopes for the Serbia international striker.
During the 2018/29 campaign, Jovic scored 17 goals in the Bundesliga and 10 goals in the Europa League for Eintracht, and Madrid felt that the then-21-year-old would flourish under then-manager Zinedine Zidane.
It turned out to be a huge waste of money, as Jovic, now 28, scored only three goals and gave five assists in 51 matches in all competitions for Los Blancos. Jovic is now playing for AEK Athens.
2. Kaka (2009-2013)
Real Madrid made Kaka the most expensive footballer in the world at the time when they paid AC Milan £56m to sign the Brazilian attacking midfielder in the summer of 2009.
During his time at Milan, Kaka was one of the best playmakers in the world and was a joy to watch.
Winner of the 2007 Ballon d’Or, Kaka clinched Serie A and the Champions League with Milan.
While at Madrid, the former Brazil international won LaLiga and the Copa del Rey, but he failed to consistently produce the magic that he weaved at Milan.
Injuries were a major reason why Kaka struggled to make a huge impact at Madrid, and he did not fit (then and now) manager Jose Mourinho’s tactics either.
While it would be wrong to say that Kaka was a ‘flop’ at Madrid, the transfer fee, wages and expectations meant that the Brazilian ended up being one of the worst signings for the club.
1. Eden Hazard (2019-2023)
When Eden Hazard joined Real Madrid from Chelsea in the summer of 2019, he was 28 and was in his prime.
No one batted an eyelid at massive fee that Madrid were paying the Blues – £89m initially, with add-ons taking it to over £150m.
However, it proved to be a monumental waste of money as persistent injuries left Hazard unable to make any impact whatsoever.
The former Belgium international attacking midfielder/winger was able to make only 76 appearances for Los Blancos, scoring seven goals and providing 12 assists in the process.
Hazard did end up winning LaLiga twice and the Champions League once during his time at Madrid, but Los Blancos would have won those trophies without the Belgian maestro.
Hazard eventually decided to retire from football in October 2023 when he was only 32 years of age.
