15 players who joined Real Madrid – and regretted it

Careful what you wish for

The roar of the Bernabeu, the allure of the crisp white shirt, the history of global domination and prospect of future European glory.

There are plenty of factors that attract the world’s best players to Real Madrid, and there is no shortage of stars who regularly shine on the biggest stage for the Liga giants.

However, as Eden Hazard weighs up his future at Chelsea with one eye on the Spanish capital, he may want to cast an eye over some of these cautionary tales where the jump came at the wrong time...

Jonathan Woodgate (€20m, 2004)

Woodgate had such potential that he received an England call-up aged 19. He fought Rio Ferdinand and Lucas Radebe for a place at Leeds and later impressed sufficiently at Newcastle that Madrid bought him along with Owen in 2004.

However, the defender was as injury-prone as he was talented. He made just nine starts over three seasons in Madrid and didn’t manage any during his debut campaign. In September 2005 he finally made his bow against Athletic Bilbao, but scored an own goal before being sent off.

In 2007, Woodgate was voted the worst buy of the century by Marca readers and sent back home to Middlesbrough for £7m after a successful loan stint back at his boyhood club in 2006/07.

Royston Drenthe (€14m, 2007)

Exciting young wide player Drenthe arrived from Feyenoord fresh off winning the U21 European Championship with Holland in August 2007.

He arrived in Spain at the same time as fellow Dutchman Wesley Sneijder and started impressively, scoring a 40-yard screamer on his debut against Sevilla. However, a lack of discipline was ultimately Drenthe’s downfall and, after featuring regularly in his first season in Madrid, his game time became more limited and his popularity with the fans diminished.

He was booed by the Bernabeu crowd during a game against Deportivo La Coruna, an incident that left him suffering with anxiety. Loans to Hercules and Everton followed before he eventually left Los Blancos for good in 2012 to join Alania Vladikavkaz in Russia.

Antonio Cassano (€5m, 2006)

Cassano scored four goals in 19 games for Madrid. He also was suspended for disrespecting boss Fabio Capello, said on air that he’d walk back to his homeland to re-join Roma, got injured and ended up on loan to Sampdoria a year later.

No one was very happy – unless you count a member of hotel staff who was presumably tipped very well for his services.

“In Madrid I had a friend who was a hotel waiter,” Cassano said in his autobiography. “His job was to bring me three or four pastries after I had sex. He would bring the pastries up the stairs, I would escort the woman to him and we would make an exchange: he would take the girl and I would take the pastries.”

Nuri Sahin (€10m, 2011)

Sahin showed immense promise from very early on in his career, debuting for Dortmund aged 16 – a Bundesliga record – and racking up more than 100 appearances before the age of 23. His ascendancy inevitably drew the attention of Real, who brought in the midfielder on a six-year deal after he helped Dortmund to the Bundesliga title in 2011.

Excited by the prospect of working under Jose Mourinho, Sahin had to wait until November to make his debut following injury and made just three more appearances all season. Loan moves to Liverpool and back to Dortmund followed in the following two campaigns, before he returned to his boyhood club permanently in 2014, having played just four games in the famous white shirt.

Didi (1959)

Didi was the reigning World Cup-winning captain when he joined Real Madrid for the 1959/60 season. He was used to being the focal point of the side, but Madrid already had its alpha male in Alfredo Di Stefano.

The Argentine wasn’t happy when Didi was unveiled to fans as “the world’s greatest player” and his eventual successor, but when he struggled to Spanish football and a team was based around Di Stefano, he was loaned to Valencia and then back to his Brazilian club, Botafogo.

Didi hated the game in Spain, but had the last laugh, winning the World Cup again in 1962 – a tournament Di Stefano never played in.

Kaka (€67m, 2009)

Kaka arrived in Madrid from Milan for a world record fee in 2009, at his peak aged 27 and with Champions League, Ballon d’Or and World Player of the Year gongs to his name.

However, injury slowed his momentum and he was ruled out for eight months in 2010 before subsequently picking up several less serious niggles. Mesut Ozil’s arrival didn’t help either.

Kaka was the star in Milan, but just another galactico in Spain. He felt unwanted, struggled to convince Jose Mourinho of his fitness, and eventually returned to the Rossoneri in 2013 with one Liga trophy and 29 goals from 120 games for Madrid. A decent return, but nothing like what his talent demanded.

Michael Owen (€12m + Antonio Nunez, 2004)

Owen scored a minimum of 16 goals in six of his seven full seasons at Liverpool, but became restless as they failed to fight for the league title and headed to Spain for a cut-price fee.

The 24-year-old had scored 142 goals for club and country but after his move to Madrid, which lasted just one season, he produced only another 64 before his retirement in 2013.

At the Bernabeu, Owen was competing with Ronaldo and Raul for a starting spot, rather than Emile Heskey and El Hadji Diouf back at Anfield. The England striker still started 26 games and scored 17 goals, but he returned to England with Newcastle the following summer as Los Blancos splashed out €25m on Robinho.

Nicolas Anelka (€35m, 1999)

After two successful seasons at Arsenal, Anelka joined Madrid in 1999. Fast and powerful, but also temperamental, the Frenchman scored against Barcelona in a Clasico triumph and twice against Bayern Munich in the Champions League semi-finals, once in each leg.

However, his time in Spain was not a success. Anelka was suspended for 45 days after a fall-out with coach Vicente del Bosque and later claimed that certain players didn’t like him because he took Raul’s place in the team.

He lifted the Champions League in his one and only season in Spain before moving on to PSG, where he again fell out with his coach. He represented nine different teams, 12 spells altogether, in the 15 years that followed.

Robert Prosinecki (€15m, 1991)

One of the most gifted players of a golden age for football in Yugoslavia, Prosinecki headed to Madrid in the summer of 1991 after inspiring Red Star Belgrade to the 1991 European Cup months earlier.

Huge expectations were placed on the 22-year-old winger’s shoulders, but he was up against it from the start as he suffered from a series of injury problems. Prosinecki played just three times in his debut season for Madrid, but made his mark by scoring with a free-kick in El Clasico.

That proved to be the highlight of three seasons in the capital, though, as he failed to live up to his price tag before plummeting in the estimations of the Blancos faithful by joining hated rivals Barcelona in 1995.

Asier Illarramendi (€32m, 2013)

Illarramendi earned a dream move after his midfield performances helped Real Sociedad reach the Champions League for the first time in a decade. He had impressed enough to merit a price tag that made him the most expensive Spanish player in Real Madrid’s history.

He went on to make a good number of appearances in the capital, scoring three goals in 90 games over two seasons, but struggled to tie down a regular starting spot in a Merengues midfield packed with stars.

In 2015, just two years into his six-year contract, he was back where started after re-joining Sociedad on a permanent deal for a fee reported be around €16m – half of what Madrid had paid for him two years before.

Mateo Kovacic (€29m, 2015)

Hazard need not look far for a warning sign. Kovacic, who has been keeping the likes of Cesc Fabregas and Ruben Loftus-Cheek out of the Chelsea team this season, moved to Madrid in 2015 after two eye-catching seasons with Inter.

Initially the Croatian’s versatility proved an asset as he started in various positions under Rafa Benitez. But when Zinedine Zidane took over and stopped tinkering with the starting line-up, Kovacic was never going to get push out Luka Modric, Toni Kroos and Casemiro.

After 37 league starts in three years, he was sent on loan to the Blues.

Walter Samuel (€25m, 2004)

Samuel had been a defensive rock in Argentina and Italy for seven years. Nicknamed ‘the Wall’, he was as solid and ruthless a centre-back as there was in the game.

But in one season for Madrid, the ill-fated 2004/05 campaign in which all four summer signings suffered, he struggled for form as Los Blancos crashed out of the Champions League in the last 16 and finished second in La Liga to Barcelona.

Samuel left for Inter, where his reputation was restored. At San Siro, however, he played behind solid midfielders like Esteban Cambiasso and Thiago Motta, and alongside steely full-backs like Javier Zanetti and Cristian Chivu. At Madrid, full-backs Michel Salgado and Roberto Carlos were essentially wingers, and the only remotely defensive midfielder was Thomas Gravesen.

Agne Simonsson (1960)

Swedish forward Simonsson was another star of the 1958 World Cup who fell foul of Di Stefano at Real Madrid. The 23-year-old was brought in to bolster the strike force in 1960, with the ageing Argentine given a deeper role.

The Blond Arrow, who still thought of himself as the Madrid’s best striker and best midfieder, wasn’t having any of it.

He often took up positions further forward, undermining Simonsson’s role in the team. The Swede played just three games for Real, was loaned out to Real Sociedad, and then in 1963 went back to his home club in Sweden, Orgryte.

Pedro Leon (€10m, 2010)

"You talk of Pedro Leon as if he is Zidane or Maradona or Di Stefano. Last year he was playing for Getafe! I don’t have to justify his absence." The words of – you guessed it – Jose Mourinho, when quizzed about why his €10m summer signing wasn’t getting game time.

Leon has since said he felt ‘humiliated’ by his treatment in Madrid and insists he worked hard, but he became another name in the long list of players to fall out of favour with the Portuguese, who wasn’t happy with his work ethic.

The winger had impressed for Getafe the previous season, but was back there on loan a year later, having played just six league games for Madrid.

Danilo (€31.5m, 2015)

The highly-rated Brazilian arrived from Porto in 2015, but failed to do much other than stand in for Dani Carvajal when the preferred right-back was unavailable. Not so much regret, then, but perhaps disappointment that he's not still there winning the Champions League. 

Danilo has since said that he found the intense scrutiny of his Madrid performances difficult to deal with, but admitted that he still missed Spain. “I had two incredible years winning important things and the people always treated me really well, but you have to turn the page,” the 27-year-old said.

Last year Danilo joined Manchester City, where he has primarily deputised for Kyle Walker and Benjamin Mendy.