Jose Mourinho reveals the two biggest regrets of his career and one of them involved Chelsea
Jose Mourinho has revealed his two biggest regrets from his career in football management - and one of them involved Chelsea.
Mourinho is one of the most successful managers of all time, winning the Champions League twice and league titles in England, Spain, Portugal and Italy.
His career took him from being Sir Bobby Robson's interpreter-turned-assistant at Barcelona, before becoming a manager in his own right.
His first major success was with Porto, where he won the league without losing a game and lifted a shock Champions League title.
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Chelsea would beat Liverpool to his services and Mourinho would form a dynasty at Stamford Bridge, before winning a second European crown with Inter Milan.
The Portuguese then moved on to Real Madrid and won a La Liga title there, before returning to English football with Chelsea and securing a third Premier League crown.
Mourinho then had success - especially in comparison to what came after him - with Manchester United, winning three trophies in his first season, before mixed spells at Tottenham and Roma.
He's now in charge of Turkish giants Fenerbahce - and has revealed what his two biggest regrets in football management are over the past 22 years.
Mourinho reveals his two biggest football regrets
Speaking to Correire dello Sport, Mourinho explained how Real Madrid president Florentino Perez tried to convince him to carry on at the Bernabeu in 2013 despite an unsuccessful season.
But the Portuguese turned him down and watched on as Real won the Champions League the following campaign under Carlo Ancelotti, beating Atletico in the final.
He said: "If we talk about matches, a lot [of regrets] because when you lose, you always think that you could have done differently, and I've lost a lot of matches.
"If you're referring to professional choices, the not to Florentino. He told me, 'Mou, don't leave now, you've done the hard part and the good part is yet to come'.
"I knew it would be like this, but I wanted to return to Chelsea after three years in Spain of great struggles."
His second regret, he says, was not leaving Roma after they failed to win the Europa League final against Sevilla in 2023. Mourinho was sacked by Roma in January 2024.
"After Budapest," he said. "Not because of the mess [referee, Anthony] Taylor made [Mourinho was charged for abusive comments towards the match officials post-match], but because I didn't leave immediately.
"I should have left Rome. I didn't - and I was wrong."
Topics: Jose Mourinho, Chelsea, Real Madrid, Manchester United, Fenerbahce
Ryan Smart