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#3 Defending the Premier League title in 2015-16
The second season of Mourinho's second coming at Chelsea saw them romp to the Premier League summit in 2014-15, with the likes of Eden Hazard, Diego Costa and Andre Schurle playing starring roles. The following season, however, a poor transfer window which saw the arrivals of players such as Papy Djilobodji and Baba Rahman signaled their struggles for the season ahead.
Mourinho is known to have great struggles in his third season at a club, at a point where the tension and turmoil of his management starts to unravel. He was vocally critical of not just referees, but also of his players. Mourinho even went as far as falling out with club doctor Eva Carneiro for an on-field medical intervention during a draw against Swansea City.
By December 2015, Chelsea had found themselves 16th in the Premier League table, just a point above the relegation zone and some 20 points away from eventual champions Leicester City.
Roman Abramovich parted ways with Mourinho for the second time midway through the season. This time, however, it was with far more animosity and that represents a stain on his legacy.
#2 Falling out with players
Mourinho's style of man-management and motivation has made champions of great talents like Frank Lampard, John Terry, Marco Materazzi and many more who would lay their lives on the line out of loyalty to their manager.
At times, however, his pressure and motivation style has brushed players the wrong way, leading to public fallouts and broken relationships. At Real Madrid, for instance, Mourinho was critical of club legend Iker Casillas and attempted to replace the captain in the starting XI by signing Diego Lopez.
Even Sergio Ramos and compatriot Pepe were thought to have had a tense relationship with Mouriduringo in his time at Madrid. Even at Chelsea, during his second spell, the months that led up to his sacking saw widespread reports of dissatisfaction and dissent from within the ranks.
At Manchester United, Mourinho's no-nonsense style and huge expectations were seen as an attempt to reign in Paul Pogba's eccentricities, with the player often frozen out and cast out to dry in front of the media and fans when results went against them. The same pattern was repeated for Luke Shaw, with harsh post-match comments about his fitness and "football brain" that saw him ostracized from the team.
#1 Failure to promote youth
The "serial winner" Mourinho demands putting out a competitive squad every season to win trophies with little scope for errors and room for growth.
In his time at superclubs across his journey, Mourinho has given selective chances to youngsters, losing them to other clubs. The likes of Romelu Lukaku, Kevin De Bruyne and Mohamed Salah were not given chances to develop into the world-class talents they eventually became.
Jose Mourinho’s fixation on getting ready-made players primed to deliver instant results has seen lots of promising youngsters fail to get regular playing time, leading them to consider their futures elsewhere.
