While his time at Stamford Bridge felt like a rollercoaster, Jose Mourinho remains an icon of Chelsea Football Club.
Having secured a multitude of trophies over two electric stints as manager of the Blues, Mourinho is remembered fondly by Chelsea fans and media. Even upon his departure for good in 2016, the club confirmed his status as a legend of the institution.
Now, Mourinho is set to return to Stamford Bridge for a UEFA Champions League league-phase match, having only just agreed to manage Portuguese club Benfica weeks prior.
The Sporting News discusses Mourinho's time at Chelsea, why he's considered such a monumental figure at the club, and how he fits into the larger lore of Blues history.
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Why did Jose Mourinho leave Chelsea?
With two different spells in charge of Chelsea, Mourinho enjoyed the highest of highs at Stamford Bridge, plus the fallout that comes with the extreme expectations of the position.
2007
Having joined Chelsea in the summer of 2004, Mourinho was a smashing success. In his first season at the helm, he had the club top of the Premier League table and into the Champions League knockout stages.
Quickly earning a fiery reputation for confidence — or arrogance, depending on your perspective — both in the press conference and on the pitch, none could argue with Mourinho's success. He won his first trophy with the club in the 2008/09 EFL Cup, and after reaching the Champions League semifinals, won the Premier League title — Chelsea's first top-flight crown in 50 years — while setting a league points record in the process. They also set a benchmark for the fewest goals conceded in a single season, 15, which stands today.
He would lead the club to a second Premier League title the following season, the 2005/06 campaign, by an eight-point gap at the top of the table, and doing so without a star goal-scoring forward.
In 2007, despite success on the pitch, there were reports that a rift was developing between Mourinho and club ownership. However, he trudged on winning the two domestic cup competitions, repeating as EFL Cup winners and securing the FA Cup title, giving Mourinho all three domestic trophies just two years into the job.
Yet the internal turmoil would eventually become too much to bear, and Mourinho surprisingly left the club in September of 2007, just a month into his fourth season at the club, with Roman Abramovich making a bold decision to part ways.
The minutia of his departure were not divulged, but it's believed that the appointment of Avram Grant first to the director of football position and then to a seat on the Chelsea board resulted in Mourinho becoming distanced from the club hierarchy. Grant then replaced him as manager, lasting just eight months in the role.
2016
A lot happened between Mourinho's stints at Chelsea. He would go on to coach at Inter Milan and Real Madrid, winning three combined league titles (two in Italy and one in Spain) and would lift the Champions League trophy with Inter, which remains the last time an Italian club won the competition as of 2025.
Mourinho told the media at the time of his return, the summer of 2013, that Chelsea was the "most important" club to him.
That passion would lead to more success. While there was no silverware in his first season back, the third-place Blues were just four points shy of league winners Manchester City in a crowded title fight, and reached the semifinals of the Champions League in the process. Mourinho would deliver in his second season back, winning the 2014/15 league crown while also pairing that with his third EFL Cup title with the Blues.
Despite signing a new four-year contract in the summer of 2015 following his third league title, things devolved quickly, this time due to on-field struggles. The club picked up just 11 points in their first 12 matches, and Mourinho would be out of a job by December having endured nine defeats in the first 16 games of the season.
"The club wishes to make clear Jose leaves us on good terms and will always remain a much-loved, respected and significant figure at Chelsea," the club statement read upon his departure.
How many Premier League titles did Jose Mourinho win?
Mourinho won three Premier League titles while in charge of Chelsea.
While he would also spend time at the helm of Manchester United and Tottenham, he would not manage to top the league table with any other English club.
Through his entire managerial career, Mourinho has won eight domestic league championships. In addition to his three in England, he won two in Italy (both with Inter Milan), one in Spain (while in charge of Real Madrid), and two in Portugal (with Porto) at the start of his managerial career.
Is Jose Mourinho Chelsea's most successful manager?
In terms of Premier League titles, yes, Mourinho is Chelsea's most successful manager, having secured three of the club's six domestic league championships.
Mourinho's win percentage is also the highest of any permanent Chelsea manager, having won 67 percent of his 185 matches in charge of the club, which is just slightly higher than the marks of Avram Grant (36 wins in 54 matches) and Antonio Conte (69 wins in 106 matches).
However, there are other managers who can boast success in other departments that Mourinho failed to accomplish.
In terms of total wins across the history of the club, Mourinho sits sixth, although he is top of any manager in the Premier League era. His 124 total victories pale in comparison to David Calderhead, who from 1907-1933 won 385 matches, more than double any other head coach in the club's history.
Additionally, Mourinho never managed to win a European title with the club. Roberto Di Matteo and Thomas Tuchel are the only two managers to lift the UEFA Champions League trophy while at Chelsea.
Why is Jose Mourinho called 'The Special One'?
Mourinho ended up accidentally giving himself the nickname "The Special One" early in his time at Chelsea.
In his introductory press conference after agreeing to manage Chelsea the first time in 2004, Mourinho was asked by Jim Cockin, then of Sky Sports, quite a simple question: why he chose Chelsea FC. His response, a long, meandering journey of an answer, produced one of the most iconic lines in modern football press-conference history.
Speaking about the idea of "modern" football managers being somehow more desirable, Mourinho said: "I have loved football since I can remember and I understand the evolution of football and the modern needs of football.
"I'm not a defender of old or new football managers. I believe in good ones and bad ones, those that achieve success and those that don't.
"Please don't call me arrogant, what I am saying is true. I'm European champion, I'm not one of the bottle. I'm a special one."
That last part, which at the time was simply referring back to his previously mentioned idea of "good ones and bad ones," became iconic, and forever linked to Mourinho who was instantly referred to as "The Special One."
The rest is history. In an era before social media was engrained in the everyday media cycle, this moment was electric.
"The minute you heard the 'special one' quote, you knew it had a ring to it," Cockin said of Mourinho's line. "It was all over the newspapers the next day, it was everywhere — and in the media landscape in those days, it kind of baked itself into the national narrative from an early point."