The Special One was at the peak of his powers when he managed in Spain. He ended the dominance of Pep Guardiola’s Barcelona during his three years in the Spanish capital but left after an eventful final year, where Real Madrid missed out on several trophies.
Florentino Perez urged Mourinho to stay at the Bernabeu, insisting that the best years were still to come. However, the Portuguese coach chose to return to Chelsea, where he had left in 2007.
Mourinho would go on to claim a third Premier League title during his second spell at the Blues, but his tenure lasted just over two years before he was dismissed. Reflecting on his decision, he concedes that staying at Madrid would have been the better move.
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He told Corriere dello Sport: “The ‘no’ to (Real Madrid president) Florentino Perez (is one regret). He said to me: ‘Don’t leave, you’ve done the hard part and the best part is yet to come.’ I knew it was true, but I wanted to return to Chelsea after three years of great challenges in Spain.”
Mourinho is still highly regarded at both Chelsea and Real Madrid, having won league titles with both clubs, but his success has waned since being sacked by Chelsea in 2015.
He has since managed Manchester United and Tottenham, with Roma being the second Italian club he took charge of. In his first season, the Special One led Roma to victory in the Europa Conference League, and the following year, he aimed for the Europa League. Roma faced specialists Sevilla in the final, and despite taking the lead, they lost on penalties, which sparked a famous outburst aimed at referee Anthony Taylor and resulted in a hefty punishment for Mourinho.
Looking back, the iconic manager wishes he had left Roma immediately after the defeat, but instead, he stayed on and was sacked seven months later.
He said: “I have to talk about Budapest (the venue of the final). Not because of the confusion with Anthony Taylor, but because I didn’t leave straight away. I should have left Roma straight away. I didn’t, and it was a mistake.”
