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#3 Iker Casillas
Despite winning La Liga in the 2011-12 season, cracks began to appear in the relationship between Real Madrid and Mourinho soon after. A big part of these cracks was caused by the Portuguese’s feud with goalkeeper and club legend Iker Casillas, who had been established as Real’s #1 for practically a decade.
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December 2012 saw Casillas dropped in favour of the unheralded Antonio Adan, and the result was a shocking 3-2 loss to Malaga. Mourinho claimed he’d dropped Casillas for “purely technical” reasons. But it was clear that the Real fans weren’t happy with the decision.
‘San Iker’ was eventually restored to his #1 spot, but when he broke his hand and was sidelined, things became even more fractious. Reports emerged suggesting that Casillas – alongside other senior players such as Sergio Ramos – had told Los Blancos president Florentino Perez that if Mourinho wasn’t forced out in the summer of 2013, they would leave instead.
The result saw both the Real fanbase and the dressing room split between those siding with the senior players, and those siding with Mourinho. Some Real fans even labelled Casillas a “mole”, feeling that a lot of the leaks to the press regarding the feud were coming from the keeper himself.
In the end though, Mourinho was forced out – leaving the Bernabeu by mutual consent at the end of the campaign. As for Casillas? He ended up being restored as Real’s first-choice goalkeeper. But his relationship with the Madrid fans was arguably never truly repaired and he departed the club just two summers later.
#4 Luke Shaw
While Mourinho’s feud with Paul Pogba tended to make the most headlines during his period as Manchester United boss, the Frenchman wasn’t the only player to fall foul of the Portuguese. Left-back Luke Shaw constantly found himself being criticised by his manager. He was even frozen out entirely by him for a time before Mourinho departed Old Trafford in December 2018.
Shaw’s fitness, commitment to training, and weight were all called into question by the Portuguese. And in April 2017, he was criticised Shaw for his on-pitch decision-making, with Mourinho stating that to succeed, he’d need to “change his football brain”.
Things didn’t improve for the left-back during Mourinho’s second season in charge of United, as he was hauled off at half-time during an FA Cup game with Brighton & Hove Albion. Later, reports even suggested that Shaw’s teammates felt like he was being “bullied” by his boss.
The 2017-18 season ended with the left-back having made just 11 Premier League appearances for Mourinho, who clearly wasn’t happy with him.
For his part though, Shaw seemed to take the criticism on the chin, never speaking out against Mourinho in the press. By the 2018-19 season he seemed to be supportive of the Portuguese’s methods. Shaw stated in an interview that “you need a thick skin to play under this manager, but we need to fight (for him)”.
However, less than a month after the interview, Mourinho was gone from United – while Shaw remains at the club and has largely become their first-choice left-back.
#5 Tanguy Ndombele
Tottenham fans will hope the current situation between Mourinho and their record signing Tanguy Ndombele improves and doesn’t end up going the same way as his spats with Pogba and Casillas. However, the Portuguese’s critics are already looking at the issue as a marker that his time at Spurs isn’t destined to work out. Only time will tell, of course.
Essentially, when Mourinho arrived in North London in November 2019, the French midfielder was struggling for fitness. That caused the Portuguese boss to question him. But at that stage, there was no real sign that there was any kind of issue between the two.
Problems really reared their head in Spurs’ draw with Burnley this past March. Chosen to start the game in midfield alongside youngster Oliver Skipp, it was clear that Ndombele was simply not up to speed with the game.
The Frenchman found himself substituted at half-time, with Mourinho later stating that in the first half, his side “didn’t have a midfield”. He then claimed that while taking time to adapt to the Premier League was understandable, Ndombele would need to give much more than he was currently giving.
The game turned out to be the final one before the season was curtailed due to the COVID-19 pandemic. And over the break, the situation appeared to be improving when the two men were spotted training on Hadley Common – breaking the UK’s lockdown laws in the process.
When the season recommenced though, Ndombele was once again left largely on Tottenham’s bench. Mourinho has since stated that the Frenchman will succeed if given more time. But it’s also been reported that Ndombele simply doesn’t want to play for the Portuguese anymore. This is a story we can expect to run on for some time.
