#3 Michael Essien | Chelsea
In what was a strange move back in August 2012, Michael Essien had completed a loan deal to Real Madrid after Lassana Diarra's move away from the capital. The Ghanian, who was at Chelsea at the time, was convinced by a phone call from then-Real manager Jose Mourinho.
Upon his unveiling at the Santiago Bernabeu, Mourinho referred to Essien as 'his son' as it was the second time the Portuguese signed him. Mourinho was the catalyst behind the defensive midfielder's €29m move to London from Lyon.
However, things quickly went south, and he had a very underwhelming year in Madrid. The Ghanian failed to become a pivotal member of the Real Madrid midfield and could not dominate the centre of the park. His tackles per game took a massive hit from 1.5 in the Premier League in 2011 to a mere 0.5 in his LaLiga adventure.
Essien was also accountable for a handful of individual errors during his time in Madrid as he failed to keep up with the opposition. On the other hand, there were also reports that he didn't get along well with the Blancos' squad, which only made matters worse.
All in all, it was an uneventful move for both Real and Essien, who played over 30 games in his solitary year away in Madrid.
#2 James Rodriguez | AS Monaco
Colombian superstar James Rodriguez has had one of the most well-documented falls from grace in recent times. The playmaker was in massive demand back in 2014 when he announced himself on the biggest stage there is — the World Cup.
James' scintillating displays in Brazil were absolutely phenomenal, and he won the Golden Boot for his six goals in the tournament. He also won the Puskas Award for his breathtaking volley against Uruguay from outside the box.
Naturally, Real Madrid were in for the services of a player such as James and signed him for approximately €70m. After getting off to a good start under then-manager Carlo Ancelotti, things quickly turned around since Zinedine Zidane's appointment as manager.
Although he won two Champions League titles and a LaLiga, James wasn't happy with the minutes he received and went to Bayern Munich on a two-year loan.
Upon his return, things are at an all-time low for James as he's managed just five LaLiga starts in the 2019/20 season. Real are actively attempting to sell the Colombian as he's one of their highest earners, drawing roughly €8.5m-a-year. There are rumours linking him with a move to Real's cross-town neighbours Atletico Madrid and Manchester United.
He was the last 'galactico' signing made by Real Madrid for five years, until their capture of Eden Hazard in 2019. It's safe to say that it unfortunately hasn't worked out by any stretch for James.
#1 Kaka | AC Milan
Speaking of Galactico signings that didn't work out for Real Madrid, there is not a more baffling transfer than that of Kaka. The AC Milan icon moved to the Bernabeu in 2009 for a fee of €68.5m amidst much hype and anticipation. The move came two years after his Ballon d'Or win in 2007 with AC Milan. The Brazilian was the last player to lift the Golden Ball ahead of the decade-long dominance of Lionel Messi and Ronaldo.
However, the superstar's move to the capital was an uneventful and forgettable one due to a combination of reasons. Kaka's recurring injuries and unavailability for sustained periods played a part in the club's and fans' frustrations surrounding him.
If that wasn't enough, the arrival of Mesut Ozil was a reason for further speculation. He had to compete with the likes of Angel Di Maria, Karim Benzema, and a host of other stars at the Bernabeu. Although Kaka is arguably a superior player to most players at the club, he couldn't handle the pressure of needing to perform week in week out.
The Brazilian's numbers took a hit, having achieved double figures for either goals or assists just once in his three years at Madrid. There were rumours towards the end of every campaign regarding a potential departure from the Bernabeu, and eventually, Kaka's exit materialised. He moved back to AC Milan and then to the MLS just a year later.
Kaka's failed move to Real Madrid is the leading example of the fact that not all transfers work out as perfectly as they would've hoped. He remains the biggest name in modern football to succumb to the pressure of the daunting Santiago Bernabeu faithful.
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