Jose Mourinho had a legendary spell at Real Madrid, taking over as first-team coach after replacing Chilean Manuel Pellegrini following a triumphant tenure at Inter Milan. While he fell short of securing the club’s coveted 10th Champions League title, Mourinho left an indelible legacy by capturing other trophies and revitalizing the team’s spirit. However, despite his impactful time at Real Madrid, Mourinho’s pick for the best player of the generation took many by surprise, sparking widespread discussion.
Jose Mourinho, one of the most decorated managers in soccer history, has never been one to shy away from expressing his opinions. In an interview with TNT Sports, he was asked to name the one player he wished he had signed during his managerial career. Mourinho did not hesitate, saying: “Of course I would have to say the little guy. But the little guy was not coachable. But I have to say, in our generation, he was the best,” referring to Lionel Messi.
The statement comes as a surprise, considering Mourinho coached Cristiano Ronaldo at Real Madrid, another generational talent. Despite their past success together, Mourinho’s praise for Messi as the best player of the generation highlighting the unique brilliance of the Argentine star. Known for his ability to change games single-handedly.
Mourinho experienced Messi’s genius firsthand in the 2011 Champions League semi-final when the Argentine scored a memorable brace to knock Real Madrid out in Mourinho’s debut season. That performance marked a pivotal moment in the rivalry between Mourinho’s Madrid and Pep Guardiola’s Barcelona.

Jose Mourinho, Head Coach of Fenerbahce SK, gives a thumbs up prior to the UEFA Europa League 2024/25 League Phase MD3 match between Fenerbahce SK and Manchester United at Fenerbahce Suekrue Saracoglu Spor Kompleksi on October 24, 2024 in Istanbul, Turkey.
Guardiola’s tactical innovation of deploying Messi as a “false 9” also played a key role in Barcelona’s iconic 5-0 Clasico victory that same season, a humbling defeat for Mourinho’s side. Messi’s ability to excel in any role and dismantle even the strongest defenses left a lasting impression on Mourinho and the soccer world, solidifying his place as one of the greatest players in history.
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Jose Mourinho’s surprising journey at FC Barcelona before Real Madrid
Before cementing his legacy as the legendary FC Porto coach who guided the club to its second Champions League title, Jose Mourinho began his journey at FC Barcelona. Initially joining the Catalan side as a translator, Mourinho later served as an assistant coach under Sir Bobby Robson and then Louis van Gaal. During his time at the club, he left behind a memorable phrase that continues to resonate in Barcelona: “Today, tomorrow, and always with Barca in my heart.”
Mourinho’s rivalry with Barcelona grew intense after he became Real Madrid’s coach. His battles with Pep Guardiola’s Barcelona, especially in El Clasico, became iconic. Mourinho often used defensive tactics to counter Barcelona’s attacking style, creating memorable clashes.
The rivalry was more than just about soccer since it represented two different philosophies. Mourinho’s approach was pragmatic, while Guardiola’s was all about possession. This competition added a fierce edge to one of the biggest rivalries in world soccer.
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