Jose Mourinho Reveals the Two Biggest Regrets of His Career—One Involved Chelsea
Jose Mourinho, one of the most decorated football managers of all time, has revealed the two biggest regrets of his illustrious 24-year managerial career. Despite winning league titles in four different countries and securing two Champions League trophies, even the “Special One” has moments he wishes he could change.
From Humble Beginnings to Legendary Status
Mourinho’s journey in football began as Sir Bobby Robson’s interpreter and assistant at Barcelona. From there, he carved out his own managerial legacy. His first major success came with Porto, where he achieved an unbeaten league campaign and a shocking Champions League triumph in 2004.
This success caught the attention of Chelsea, who secured his services. Mourinho’s first stint at Stamford Bridge saw him establish a dynasty, winning back-to-back Premier League titles and numerous domestic honors. His career then took him to Inter Milan, where he achieved an unprecedented treble, and Real Madrid, where he broke Barcelona’s dominance by winning La Liga in record-breaking fashion.
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Returning to Chelsea in 2013, Mourinho added another Premier League title to his tally before moving on to Manchester United, Tottenham Hotspur, and Roma. At United, he enjoyed a successful first season with three trophies, including the Europa League. At Roma, he guided the club to a UEFA Europa Conference League victory—the first European title in their history—before mixed results led to his departure.
Now managing Fenerbahce in Turkey, Mourinho reflected on two pivotal decisions that he considers the biggest regrets of his career.
The Regret Involving Chelsea
Speaking to Corriere dello Sport, Mourinho revealed that his first regret stemmed from his decision to leave Real Madrid in 2013. Despite a challenging final season at the Bernabéu, Real president Florentino Pérez urged Mourinho to stay, believing the club was on the verge of greatness.
“Florentino told me, ‘Mou, don’t leave now, you’ve done the hard part and the good part is yet to come,’” Mourinho said. “I knew it would be like this, but I wanted to return to Chelsea after three years in Spain of great struggles.”
Embed from Getty ImagesHis departure paved the way for Carlo Ancelotti to take over at Real Madrid. Under Ancelotti, the club won the Champions League the following season, defeating Atletico Madrid in the final. For Mourinho, the decision to leave before reaping the rewards of his work remains a significant regret.
The Roma Episode
Mourinho’s second regret came during his tenure at Roma. After guiding the club to the Europa League final in 2023—a match they lost to Sevilla—Mourinho admitted he should have parted ways with the Italian side.
“After Budapest, I should have left Rome,” he confessed. “Not because of the mess referee Anthony Taylor made, but because I didn’t leave immediately. I didn’t—and I was wrong.”
Mourinho’s decision to stay ultimately backfired. His relationship with the club deteriorated, and he was dismissed in January 2024.
Lessons from a Storied Career
Mourinho’s reflections offer a rare glimpse into the mind of a manager known for his confidence and success. While his career is marked by incredible achievements, these moments of self-doubt highlight the challenges even the greatest managers face in their decision-making.
As Mourinho continues his journey with Fenerbahce, his story remains a testament to the highs and lows of elite football management. Fans and pundits alike will wonder how his career might have unfolded differently had he made other choices. But one thing is certain: the “Special One” has left an indelible mark on the game.
Jose Mourinho Reveals the Two Biggest Regrets of His Career—One Involved Chelsea
