Mourinho is currently managing the Turkish club Fenerbahçe. While the stature of the teams he’s managed in recent years has declined, his career still boasts an impressive roster of players.
From his Premier League-winning team in 2004/05 to his 2009/10 successes, Mourinho has had the opportunity to work with football icons like Samuel Eto’o, Didier Drogba, Frank Lampard, and Cristiano Ronaldo…Continue Reading
Yet, despite his many accomplishments, the Portuguese coach still regrets not managing a few players—one, in particular, might surprise fans.
Even though he led top clubs like Manchester United, Real Madrid, and Inter Milan, Mourinho often found himself devising strategies to stop Lionel Messi, rather than having the chance to coach him.
“For example, I never got to train Lionel Messi, but then nobody can train Messi,” Mourinho told YouTuber OHM earlier this year.
“It is absurd to think you could coach him, because he was born with everything and already knows everything. He might teach you some things. All you could say is that you had the honour of having him in your squad.”
At the time, Mourinho was manager of Serie A team Roma, which may have influenced some of his choices.
“To stay in the Roma theme, I would’ve liked to have [Daniele] De Rossi at Inter and Real Madrid, but it was not possible.
“I also wanted [Francesco] Totti at Inter, despite his age at the time, but it was not possible either. These are players I always wanted in my career,” added the 61-year-old.
Although Mourinho’s trophy count has dwindled in recent years, he was still regarded as a hero in Rome. He led the club to victory in the Europa Conference League in 2022 and was emotional upon leaving the club in January 2024.
In a twist of fate, Mourinho’s successor in Rome was De Rossi, though he too has since left the club.
Mourinho never had the opportunity to manage De Rossi or Totti, and with Lionel Messi now 37 and playing for Inter Miami in the MLS, it’s unlikely their paths will ever meet either.
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