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Since Sir Alex Ferguson retired in 2013, only two managers have brought silverware to the club. Mourinho brought in the Carabao Cup and the Europa League, whilst Dutchman Louis van Gaal won the FA Cup.
Despite a more than promising start to his time at United, Mourinho’s tenure soon started to fall apart. ‘The Special One’ was eventually sacked in December 2018 after a 3-1 defeat by Liverpool at Anfield a few days prior.
Now at Roma, the 59 year-old has somewhat rebuilt his reputation, having successfully led the Italian club to the final of this season’s Europa Conference League, the club’s first European final in 31 years.
With his former employers United currently struggling, it looks like Mourinho will again have the last laugh if he is to bring home a trophy during his first year as Roma boss.
Modern football can be a cruel place to be, and Mourinho, along with Real Madrid boss, Carlo Ancelotti both experienced criticism about their coaching style, with many questioning whether both coaches were too outdated to still be involved today.
Mourinho however, has defended himself and his Italian counterpart, stating that their former clubs were the issue, not them.
He said: "I believe that the problem with Carlo Ancelotti was that when you coach Everton you are not about to win the Champions League.
"And with me, you know, people they saw me taking up jobs where they thought that I could win trophies but they were not jobs where we were expected to lift trophies."
The Portuguese also added that he will be the one to call time on his stellar career.
He said: "It's a matter of quality, motivation, passion. Without passion you are finished. Without pressure in the build-up to big games you are finished. I know very well myself, I know very well Carlito as well, but there are more examples that we could make.
"But we are the ones who will call it when we want to stop, and I’m afraid people will have to wait a long time before I say that it’s over!"
Roma will face Dutch side Feyenoord on Wednesday 25 May as the two teams battle it out to become the first winner of the Europa Conference League.