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#3 Jonathan Woodgate
Jonathan Woodgate didn’t cost Real Madrid as much as some of the other players on this list – they paid Newcastle United around £13m for his services in 2004. However, it’s safe to say that the England defender was a massive flop at the Bernabeu.
Injured at the time of his transfer to Los Blancos, Woodgate failed to make a single appearance in his first season at the club.
And when he finally did pull on the famous white shirt in September 2005, his debut was a sheer disaster.
Woodgate was on the winning side as Real defeated Athletic Bilbao 3-1, but he also scored an own goal before being sent off for two bookings.
The England man recovered from his awful start to put together some decent performances for Real. But just as he’d begun to break properly into the first team, injuries struck again and left Woodgate back on the shelf.
By the time the 2005-06 campaign ended, Woodgate had made a total of 14 appearances for Real. The summer saw him move back to the Premier League in a loan move to Middlesbrough, and a year later, it was made permanent.
Incredibly, 2007 saw Woodgate voted Real Madrid’s worst signing of the 21st century by readers of Marca – summing up the defender’s diabolical time at the Bernabeu.
#4 Theo Hernandez
When Real Madrid parted with €24m to meet defender Theo Hernandez’s release clause in the summer of 2017, the move didn’t come without controversy.
The French left-back had spent the 2016-17 season starring for Alaves, appearing in 32 of their 38 La Liga matches. However, he was on loan at the club from his boyhood side – Real Madrid’s city rivals Atletico Madrid.
And so when Los Blancos decided to bring him to the Bernabeu, to say Atletico weren’t impressed would be an understatement. Unfortunately for Hernandez, his old club need not have worried.
The Frenchman made just 23 appearances in all competitions during his first campaign at the Bernabeu, struggling for form and managing just 10 starts in La Liga. And rather than have patience with him, the 2018-19 season saw Los Blancos loan him to Real Sociedad.
While he did fare a little better there, it wasn’t enough to impress the powers-that-be at Real Madrid. And so, in the summer of 2019, he was sold to AC Milan for just €20m.
Essentially, considering the hassle they went through to sign him, Hernandez simply wasn’t worth the bother.
#5 Eden Hazard
The Premier League has always been one of Real Madrid’s favorite places to shop for players, with stars like Gareth Bale, David Beckham, and Cristiano Ronaldo heading to the Bernabeu from England over the years.
And in the summer of 2019, Los Blancos turned back to England’s top flight for their latest Galactico. They brought in Chelsea’s Eden Hazard for a fee of over €100m, making the Belgian winger one of the most expensive players in history in the process.
Hazard had arguably been the Premier League’s best player over the preceding few seasons, but to say his move hasn’t come off just yet would be a massive understatement.
His debut season was horrendously curtailed by injury, but questions also abounded over his professionalism after he reportedly arrived at his new club overweight.
The Belgian made just 16 league appearances during 2019-20 and only managed to score one goal.
The current campaign has gone equally poorly for Hazard. After apparently returning to training out of shape again, the former Chelsea man has started just eight games across all competitions, scoring only three goals.
At the age of 30, it’s probably too late for him to resurrect his career at the Bernabeu – meaning he’ll probably go down as one of Real Madrid’s all-time most expensive flops.
