The legendary Portuguese manager took over from another legendary tactician, Louis van Gaal, at Old Trafford when the Dutchman failed to hit the heights the club reached under Sir Alex Ferguson despite winning the FA Cup in 2016.
Mourinho went on to win the Community Shield, the Carabao Cup and the UEFA Europa League in addition to Van Gaal’s FA Cup, and those titles are the last titles that Man United have won since then. He was later sacked and replaced by Ole Gunnar Solskjaer, who also suffered the same fate but without winning any titles.
The former Chelsea boss went on to Tottenham and in two years, was axed from the role. Mourinho would later accept a job as the manager of AS Roma, returning to the Serie A for a second time after leading Internazionale to the only treble in Italian history back in 2010.
He has now led the Giallorossi to the UEFA European Conference League final, their first European final in 31 years, beating the allegations that he had become outdated for the big leagues.
After reaching the final, Mourinho sent a word of congratulations to his friend Carlo Ancelotti who managed Everton and was also in the same position as he was in the Premier League.
Ancelotti confirmed his place in the UEFA Champions League final that same week and Mourinho charged them both to go and win the finals.
In the final press conference of the season in the Serie A, Mourinho was asked about those comments and if he believed that the critics were wrong about him and Ancelotti. The former FC Porto manager instead mentioned the fact that the teams both he and Ancelotti managed were not expected to win titles in the first place.
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. But when you have such a winning career on a cyclical basis so to speak, you can expect that, people can say that.
“Personally I’m not worried about this [being replaced by younger coaches]. I do not think and focus on the generations, I focus on quality.”
Mourinho also defiantly told his critics that he, as well as Ancelotti, were far from being done at the top level. “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,” he said.
“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!”