10 players who joined Real Madrid – and regretted what they wished for

Nicolas Anelka

Eden Hazard, beware. Plenty of other players have pushed for a move to the Bernabeu, only to discover it wasn’t all it was cracked up to be...

We are part of The Trust Project What is it?

Mateo Kovacic (€29m, 2015)

Mateo Kovacic

Hazard only needs to look across the Chelsea dressing room for a cautionary tale. Kovacic, the dynamic midfielder who’s keeping Cesc Fabregas, Ross Barkley and Ruben Loftus-Cheek out of the Blues’ best XI, joined Real in 2015 after two successful years with Inter Milan.

SEE ALSO Ruben Loftus-Cheek’s road is running out at Chelsea – and reaching an inevitable conclusion

At first, the Croatian’s versatility earned him sporadic starts in various positions under Rafa Benitez. But when Zinedine Zidane took over and decided not to tinker with the starting line-up, Kovacic was never going to oust Luka Modric, Toni Kroos and Casemiro from the midfield. (It's been a similar story with his national team too, where he has Modric, Ivan Rakitic and Milan Badelj for competition.)

After 37 league starts in three seasons, he was shipped out on loan to Chelsea.

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

Michael Owen

Owen was the main man at Liverpool, having netted between 16 and 19 league goals in six of his seven full seasons at Anfield. Frustrated at the Merseysiders’ failure to challenge for the title, however, he joined Madrid in 2004 for a cut-price fee.

Aged 24, Owen had 142 goals to his name for club and country in just over seven seasons. But this was the turning point in his career: after the striker’s move to Spain, which lasted just one year, he managed only 64 more in the next eight seasons leading up to his retirement at Stoke in 2013.

By the time he left Anfield, Owen only had Emile Heskey, Milan Baros, El Hadji Diouf and Florent Sinama Pongolle vying for a place. At the Bernabeu, however, he had to get past Ronaldo and Raul just to get into the team. Owen still managed 26 starts in all competitions and scored 17 times, but Madrid shelled out €25m on Robinho the following summer and Owen was sent back to England with Newcastle.

Nicolas Anelka (€35m, 1999)

Nicolas Anelka

Before he went on his world tour of clubs, Anelka signed for Madrid in 1999 after two successful years breaking through at Arsenal. Fast, direct and powerful, but also temperamental; for Real, Anelka scored against Barcelona in a 3-0 Clasico triumph and twice against Bayern Munich in the Champions League semi-finals – one in each leg.

However, this was no great success story: the Frenchman also got himself suspended for 45 days after falling out with coach Vicente del Bosque, and later claimed that certain Madrid players didn’t like him because he took Raul’s place in the side.

After just one season – albeit one that culminated in him lifting the Champions League trophy – Anelka moved on to first club PSG, where he again fell out with the coach (this time Luis Fernandez). He went on to play for nine more teams (12 altogether) in the 15 years that followed.

Antonio Cassano (€5m, 2006)

Antonio Cassano

Cassano played 19 times for Madrid after moving from Roma in 2006. The Italian maverick scored four goals, got himself suspended for disrespecting manager Fabio Capello (who he’d also fallen out with at Roma), announced on air that he’d walk back to Italy to join Roma, got injured and ended up being loaned back to Italy with Sampdoria one year later.

No one was very happy – well, unless you count one particular 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 recalled in his autobiography, Telling Everything. “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. Sex and then fold – a perfect night.”

Danilo (€31.5m, 2015)


The Brazilian came to Madrid from Porto in 2015 with a burgeoning reputation, but didn’t do much except fill in for Dani Carvajal when the first-choice right-back was injured. 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 handle, but admitted that he still missed the Spanish capital. “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.

In 2017, Danilo joined Manchester City, where he has spent most of his time as understudy to Kyle Walker and Benjamin Mendy.