The 5 worst signings in Real Madrid's history

As one of the world’s richest and biggest club – some would say the biggest outright – it’s hardly a surprise that when Real Madrid make a move into the transfer market, they tend to go hard. Los Blancos have become renowned for buying some of the world’s greatest players in the modern era, including Cristiano Ronaldo, Zinedine Zidane and Luis Figo.

Of course, not every signing they make is a big one – and not every signing turns out to be a hit, too. Real have made some truly terrible signings over the years, for huge transfer fees and for some surprisingly small ones, too.

Here are the 5 worst signings in Real Madrid’s history – with some honourable mentions, too.

Honourable Mentions

Real's purchase of Thomas Gravesen always felt like an odd one

1. Thomas Gravesen

Danish midfielder Thomas Gravesen – signed from Everton in January 2005 for a relatively small fee of £3.4m – was always a bit of an odd signing for Real Madrid to make, particularly because his style of play was not flashy in any way nor did he carry a high profile.

The Dane was bought to provide some bite to Madrid’s midfield, but the club’s fans were never enamoured with his tough-tackling style and he quickly slipped out of the starting line-up. A training ground bust-up with star striker Robinho followed after Gravesen hit him with an especially hard tackle, and just weeks later in the summer of 2006, he was offloaded by boss Fabio Capello to Celtic.

2. Pedro Leon

Signed from Getafe for a fee of €10m in the summer of 2010, winger Pedro Leon helped Real Madrid to reach the knockout stages of the Champions League in his debut season with a last-gasp equaliser against AC Milan, but that was about all he achieved at the Bernabeu.

Then-boss Jose Mourinho was apparently concerned about his fitness and work ethic in training, and so Leon was largely frozen out of the first team. And when the Portuguese boss was quizzed about why the winger was offered so little playing time, Mourinho stated that he was “no Zinedine Zidane”. It came as no surprise then when he returned to Getafe on loan just one year after his move, after playing just 14 matches for Real.

3. Elvir Baljic

Bosnian winger Elvir Baljic moved to the Bernabeu in the summer of 1999 for a surprisingly expensive fee of €26m, but the form he displayed for Turkish side Fenerbahce – 18 goals in 30 appearances – never emerged in the colours of Real.

Baljic ruptured his ACL in pre-season training before his career with Los Blancos even began, and in his debut season, he made just 11 appearances for Real – 8 of them from the bench – scoring just one goal. He was loaned back to Fenerbahce in the summer of 2000, and a further loan to Rayo Vallecano followed in 2001/02 before his Real contract was finally terminated.

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5. Julian Faubert

Julien Faubert's move to Real Madrid was bizarre by anyone's standards

A genuinely bizarre signing for Real’s standards, Frenchman Julien Faubert was signed by Los Blancos in a loan deal from West Ham in January 2009. The move was baffling given Faubert had only recovered from a ruptured Achilles tendon a year prior – an injury that had kept the winger out of action at West Ham from practically the moment he’d arrived there.

Faubert had made just 15 Premier League starts in 2008/09, scoring no goals, so quite what kind of player Real thought they were bringing in is anyone’s guess. The Spanish giants paid a loan fee of £1.5m to the Hammers and had an option to sign the Frenchman permanently, but it was hardly surprising when the deal went south quickly.

Faubert infamously missed training due to mixing up his calendar and assuming he had the day off, and was even snapped seemingly asleep on Real’s bench during a match against Villarreal. All in all, his career at the Bernabeu ended with just 2 appearances, and his baffling time at the club ended when he was sent back to West Ham for the start of the 2009/10 season.

4. Kaka

Kaka cost Real a huge amount of money for little in return

Real’s legendary Galactico policy – in other words, attempting to sign the world’s best players regardless of transfer fee or playing position – had seemingly ended midway through the 2000s, but the summer of 2009 saw it re-established in style when Los Blancos bought superstars Cristiano Ronaldo and Kaka to the Bernabeu.

But while Ronaldo naturally went on to become a huge success in Madrid – winning multiple titles in La Liga as well as four Champions Leagues and becoming Real’s all-time top goalscorer – the same could not be said for Brazil’s Kaka. The 2007 Ballon d’Or winner, who signed for a fee of €67m, could never quite translate his AC Milan form to his career at Real.

The biggest issue the Brazilian forward had at the Bernabeu was injuries; after a modest return of 9 goals and 8 assists in 33 appearances across all competitions in his debut season, he picked up a bad knee injury which sidelined him for the majority of 2010/11, restricting him to just 14 league appearances.

The Brazilian’s form improved somewhat in 2011/12 as Real won La Liga, but he was still restricted to just 27 league appearances and only scored 5 goals. By the end of 2012/13, it was clear that his best years were behind him, and he moved back to Milan that summer. Kaka’s time at Real would usually just be considered a mild disappointment – but due to his monstrous transfer fee and stellar reputation upon his arrival, it’s hard not to rank him highly here.

3. Jonathan Woodgate

Jonathan Woodgate's Real Madrid debut is considered one of the worst of all time

One of numerous highly-rated English central defenders produced in the early 2000s, Jonathan Woodgate’s move to Real in the summer of 2004 for a fee of £13.4m came as a surprise. It wasn’t that Woodgate didn’t have talent, more that the England international simply couldn’t seem to stay fit; he’d managed just 18 league games for Newcastle in his previous season.

It came as no shocker then when it was revealed that the Middlesbrough-born defender was actually injured at the time of his transfer to the Bernabeu, and so his first season ended with him failing to make his debut for Los Blancos, as he spent the entire time in the treatment room.

When he finally did make his debut – in a September 2005 match against Athletic Bilbao – things couldn’t have gone any worse. Woodgate scored an own goal in the first half and was then dismissed for a second booking midway through the second half. His performance has often been labelled as the worst debut match of all time.

Woodgate did eventually recover somewhat and established himself as one of Real’s better defenders, but his injury issues just wouldn’t go away and he ended the season with just 16 appearances in all competitions before being sent on loan to his hometown club of Middlesbrough in the summer of 2006. The move was made permanent the following summer, meaning the Englishman left Real with only a handful of appearances to his name – making his time at the Bernabeu an unmitigated disaster.

2. Nicolas Anelka

Nicolas Anelka was suspended at Real for refusing to train

There were no questions around the talent of French striker Nicolas Anelka when he made his big move to Real in the summer of 1999 for a big fee of £22.3m, but there were certainly questions around his attitude and temperament. The Frenchman had scored 17 goals in 35 Premier League games for Arsenal in 1998/99, but had also shown such little enthusiasm at the club that the British press had labelled him Le Sulk.

Unfortunately for Los Blancos, Anelka’s attitude didn’t especially change despite finally getting the big-money move he’d always craved. It took him six months to score a goal for his new club, and while it was an important goal – it came in a 3-0 victory in El Clasico against Barcelona – just a month later he found himself suspended for 45 days following a refusal to train.

Apparently the Frenchman had fallen out with head coach Vicente Del Bosque, and to make matters worse, he claimed the club had “treated him like a dog” by suspending him. Real’s President Lorenzo Sanz responded by suggesting Anelka had psychological issues; “something does not turn around properly in his head” was the quote uttered by the Spanish businessman.

It came as no surprise then when the striker was unceremoniously sold to Paris St. Germain in the summer of 2000; the only shock was that Real were able to recoup £22m for him. His time at Real Madrid ended with just 7 goals in 31 appearances, making him one of their most disastrous signings.

1. Antonio Cassano

Antonio Cassano's time at Real was an unmitigated disaster

Italian striker Antonio Cassano lasted slightly longer at Real Madrid than Nicolas Anelka, but it’s safe to say that his tenure at the Bernabeu was even more chaotic and disastrous than that of the Frenchman. The second Italian player to sign with Los Blancos, hopes were high for Cassano after he’d shown flashes of his tremendous talent with Roma, although disciplinary issues at the club should’ve raised a red flag.

The €5m fee Real paid for the Italian seemed like a bargain at the time, but evidently the club didn’t know what they’d gotten themselves in for. Cassano did score a goal on his debut for his new side in a Copa del Rey match with Real Betis, but weeks later it became clear that he was hardly in a fit state to play football; his weight ballooned and Real began to fine him for every gram he remained over his optimum weight.

His first season ended with him scoring just 2 goals in 17 games, but worse was still to come. Cassano started the 2006/07 season badly and was then suspended for disrespecting the club’s new coach, fellow Italian Fabio Capello. From there he seemed determined to leave the Bernabeu, and it came as no surprise when the striker moved to Sampdoria on loan at the start of 2007/08, after a return of just 2 goals in 12 appearances for Madrid.

Years later, Cassano revealed that while at Real, he would eat “three or four” croissants a night – and also claimed to have bedded over 600 women during his time at the club. It was also revealed that he’d labelled Capello “faker than Monopoly money” in their clash. Both stories go a long way to explaining why he’s the worst signing in Real Madrid’s history.