Real Madrid's worst signings of all time: Jovic takes his place alongside Woodgate, Kaka & more

Madrid took a massive gamble when they signed a talented but temperamental French striker who had already earned himself the nickname 'Le Sulk' in the English press. It did not pay off. Anelka lasted just one season in Spain - but it was an eventful campaign.

His first goal came in the Clasico, while he netted twice in the Champions League semi-finals against Bayern Munich.

However, there were just seven goals altogether, not least due to the fact that the forward was suspended for 45 days at one point for refusing to train, with Anelka accusing his Spanish employers of treating him "like a dog".

John Toshack had been impressed by the Bosnian during his time working in Turkey and persuaded Madrid to pay a shockingly large fee for the forward.

Baljic's hopes of making an impact in Spain were hardly helped by a knee injury shortly after his arrival but even when fit, he did not look like he belonged at the highest level and he was loaned back to Fenerbahce after just one season, and one goal, in La Liga.

He later mused: "It doesn't hurt me to see media listing me among Real's biggest flops; I don't see myself that way." The club's fans will disagree.

The fee may have been small but Cassano was still a colossal waste of money. His return was dismal - just one goal in seven appearances - his attitude dreadful and his diet even worse.

"In Madrid, I had a friend who was a hotel waiter," the Italian later revealed. "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 food, a perfect night."

Danilo has openly admitted that it is difficult to deal with the amount of scrutiny players are subjected to by the media in Madrid.

"An error, no matter how small, goes viral," he lamented. "A mistake becomes very great even if it is small. But, of course, when you do something good, it is also very great."

Surprisingly, Danilo is still playing at the very top level - Madrid offloaded him to Manchester City in 2017, before he joined Juventus two years later where he still plays.

Whether a character like Drenthe ever had the discipline to succeed at the highest level is open to debate. What we do know is that his hopes of making it at Real Madrid effectively ended the moment he was mercilessly booed by the Bernabeu crowd during a game against Deportivo La Coruna.

It left him "suffering from anxiety", then manager Juande Ramos revealed, "As his coach I will do all I can to help him because he has a lot of potential.

It was never realised, with the former teen star eventually departing for Hercules, where he made further headlines for going on strike. The Dutch winger retired at the age of 29 to focus on his rap career.

Perhaps not the worst transfer in Madrid's history but certainly the strangest. The entire football world was stunned when they took Faubert on loan from West Ham during the January transfer window.

There was an option to buy but it was never taken up, not least because the Frenchman missed one training session as he mistakenly thought he had the day off, and also appeared to nod off during a game against Villarreal.

The right-back denied it – “I didn’t fall asleep on the bench; I prefer beds” – but it adequately summed up the rather dream-like absurdity of his short spell in the Spanish capital.

A transfer 10 years in the making, Eden Hazard's move to Real Madrid appeared doomed from the moment the winger turned up overweight for pre-season training.

In fairness to Hazard, he was desperately unfortunate with injuries, having had an almost clean bill of health for the duration of his time at Chelsea.

However, even when he has managed to get a run of games together in Spain, he has looked a very cheap imitation of the player who had illuminated the Premier League for seven years.

Hazard has got his hands on some important trophies, including the Champions League, but he played about as much part in Madrid's 2021-22 triumph as Gareth Bale – and it wasn't for the want of trying on the Belgian's part, which probably makes the whole situation even sadder.

In 2018-19, Jovic looked like the next big striking star of Europe. He scored 10 goals in 14 Europa League games for Frankfurt, and also impressed in the Bundesliga.

This persuaded Madrid to pay an extortionate amount for a player who had been on loan at Frankfurt from Benfica, resulting in a complex double transfer for Jovic as he made a permanent switch to Germany before signing for Madrid the very next day.

Jovic certainly hasn't proven worth the trouble, with the Serbian now having joined Fiorentina after just three goals in 51 games for Los Blancos.

It's easy to understand why Real Madrid broke the transfer world record to sign Kaka. When he joined from Milan, he was 27 and at the peak of his powers, a Ballon d'Or winner. At the time, there was no better sight in football than the Brazilian trequartista with the ball at his feet: he didn't run; he glided.

Unfortunately, he was grounded for the majority of his time in Spain. Injuries ruined what should have been a sensational partnership with Ronaldo, while the arrivals of Mourinho and Mesut Ozil also hindered his hopes of playing regular football.

There were highlights, not to mention a Liga title, but as he admitted, "I lost the joy of playing football a bit [in Madrid]."

"I felt humiliated at Madrid," Leon admitted in 2011. "I am not aware of doing anything wrong. I did all I could, I was professional, I worked hard."

Mourinho disagreed. The Portuguese coach was disgusted by the winger's allegedly poor work ethic and eventually snapped at journalists after repeated questions over his ongoing refusal to give the €10m signing more game time.

"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." Unsurprisingly, Leon was sent back to where he came from after just one, controversy-ridden season at the club.

Big things had been expected of one of the finest talents ever to come out of the Balkans, a gifted midfielder who had just helped Red Star Belgrade win the European Cup.

The highlight of his three-year Madrid career was a goal against Barcelona in the Clasico and even that was well and truly overshadowed by the fact that he departed for Catalunya in 1995.

That he also flopped there was of little consolation to frustrated fans.

Just like everyone else in the football world, Real Madrid president Florentino Perez fell in love with the fresh-faced, silky-skilled James Rodriguez during Colombia's run to the quarter-finals of the 2014 World Cup.

Given the attacking midfielder with a keen eye for spectacular goals had long dreamed of moving to the Santiago Bernabeu, a transfer was inevitable, so James became Perez's latest Galactico.

At times during his first season in Spain, he played like one, ending the 2014-15 campaign with 17 goals in all competitions.

However, while Zinedine Zidane's appointment as coach in 2016 proved a crucial turning point in Madrid's modern history, it effectively spelt the end of James' Blancos career.

He rarely featured under the Frenchman, who at one point claimed that James had asked to be left out of a game against Athletic Club.

In the end, after a couple of years on loan at Bayern Munich, and a dire final season in which he made just eight appearances, the €80m (£68m/$86m) signing left for nothing – the perfect illustration of just how far his stock had fallen since winning the Golden Boot in Brazil.

At €25m, Samuel looked like an excellent signing for a side crying out for a dominant, ruthless centre-half. However, the Argentine never looked anything remotely like the player who had earned the nickname 'The Wall' during his time at Roma, much to the bemusement of former coach Capello.

"The fact that he did not make a name for himself at Real Madrid still surprises me," the Italian later admitted. "Perhaps it was the wrong time."

It certainly seemed that way because as soon as Samuel returned to Italy in 2005, to join Inter, he went back to being one of the finest defenders on the planet, becoming a legend at San Siro.

"Looking back," Saviola said, reflecting on his time in Spain, "I do wish I'd played more." The Argentine attacker had impressed during his early years at Barcelona but by the time he joined Madrid, it was clear that he was not going to live up to the hype.

Madrid's decision to sign Saviola did little more than annoy their Clasico rivals, as 'The Little Rabbit' never looked remotely capable of nailing down a regular starting berth in a side boasting Arjen Robben, Gonzalo Higuain, Raul, Robinho and Ruud van Nistelrooy.

Saviola moved on to Benfica after just five goals for Los Blancos.

The worst debut in history? It's hard to look past Woodgate's first game for Madrid - even though it was extremely tough to watch.

The centre-half had joined in 2004 but a spent a year out injured with a thigh problem that doctors had failed to detect. "I thought, 'Right, you're back. Show them what you can do," he later recalled of his appearance against Athletic Bilbao.

He scored an own goal and was sent off. A forgiving Santiago Bernabeu gave him a standing ovation but nobody complained when Woodgate was sent back to England in 2006 after just eight further league matches.