In their 120 years of history, Chelsea FC have had 32 permanent managers/head coaches, 6 interim managers, and 6 caretakers. 44 in total, twice the mere 22 Liverpool have had full-time since their founding, back in 1892, for further context.
Considering the wide range of people who have sat in Chelsea’s dugout over the years, particularly in the last two decades, the accolades they have earned – either individually or collectively – the coaching styles they have brought with them, and the charisma that has defined many of them, an ordered Top 5 list would be a useful approach. All these factors could serve as criteria for the list.
5 – The Caretaker Hero: Roberto Di Matteo
Aside from being initially appointed as a temporary replacement for André Villas-Boas in March 2012, club legend and up-to-that-point assistant head coach, Roberto Di Matteo defied all the odds.
With him at the helm, Chelsea FC won the UEFA Champions League trophy for the first time in their history, beating Bayern Munich at Allianz Arena after a penalty shootout.
It was the second trophy he managed to clinch in the space of a fortnight, as the Italian had also guided the club to FA Cup glory at Wembley. Goals from Ramires and Didier Drogba in each half secured a 2-1 win for The Blues, who got the better of Kenny Dalglish’s Liverpool.
Di Matteo was never a sophisticated strategist. Nor did he have a comprehensively deep philosophy that would catapult the club to sky-high levels of greatness on a consistent basis.
But his popularity, a trait he had forged during his time as a player in the late 1990s, along with his quite easygoing character, fit a wonderful spine of leaders all over the dressing room like a glove.
A demoralised and fractured collection of footballers, lacking in confidence and having lost their compass due to Di Matteo’s predecessor’s adventurously chaotic playing style, found their rhythm soon after, culminating in the most successful way possible.
Despite his evidently basic tactical acumen, “Robbie,” as called by the fans, will always have his unique place in Chelsea FC’s folklore, as a very respectable midfielder and, most importantly, as the man whose serenity and positivity led the club to find the holy grail after several failed attempts.
4 – Work, work, work, aka win, win, win: Antonio Conte
In his first press conference, the former Juventus midfielder mentioned the word “work” as many as 16 times.
After a tricky period in September, Conte changed the system into a 3-4-3/3-4-2-1, which worked remarkably well, as 13 wins in a row followed.
The workaholic attitude the fiercely demanding Italian imposed on a group of players who had finished as low as 10th a season before was instrumental in breaking the record of most wins in a single Premier League season, 30 out of 38 matches.
It was an achievement of absolute joy, delirium, and fulfilment.
The subsequent campaign was far from similar standards of splendidness, as transfer policy clashes led to an ultimate deterioration of Conte’s relationship with the club’s hierarchy. The consequences were shaped into a loss of dressing room but also an underwhelming 5th place finish for the first time since Roman Abramovich had arrived in West London.
Still, the sheer dominance of 2016/17 and an FA Cup triumph in his last game in charge undoubtedly and deservedly have the Leece-born tactician as one of the most prolific managers to have been sat at Stamford Bridge’s home dugout.
3 – Quiet Leadership at Chelsea FC: Carlo Ancelotti
In 2016, Carlo Ancelotti published his second autobiography, aptly called ‘Quiet Leadership‘. Always uncharacteristically ice-cool for a football manager, Ancelotti has embodied the title of his book wherever he has been.
Never put off by the egos of superstar players he has worked with, former Arrigo Sacchi’s assistant has pretty much been quite a success for the majority of his long and exemplary career.
And his time at Chelsea FC could not have been an anomaly. Language barrier in his early days aside, Ancelotti adapted very smoothly to the dog-eat-dog features of the Premier League.
After spending 8 years at AC Milan, in 2009-10 he brought with him his brand of distinguishable attacking football to Stamford Bridge.
He significantly increased direct goal contributions from both midfield and frontline, concluding with a record-breaking 103 goals in a single Premier League season.
More concretely speaking, Frank Lampard scored 27 goals and recorded 16 assists in all competitions, whereas Drogba, at the age of 32, enjoyed his best individual season ever. The striker found the back of the net 37 times in 44 games, assisting 13 times in the process.
As of today, Real Madrid’s current manager is the only man to have won The Double with Chelsea FC.
After knocking Sir Alex Ferguson’s Manchester United off their perch for the first time in 4 years, the 5-time Champions League winner added the FA Cup in the bag a week after. Chelsea beat a financially distressed Portsmouth 1-0, courtesy of a Didier Drogba free-kick strike.
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2 – The German Rulebreaker: Thomas Tuchel
Thomas Tuchel incarnates the closest version of José Mourinho to defend Chelsea’s colours.
A package of attributes – dripping in charisma, a tactical chameleon, and more specifically, a hybrid of the Spanish possession-based tiki-taka of the 2008-2012 golden generation and the German gegenpressing style of the post-2000 era.
To paraphrase Michael Cox in his comprehensive book Zonal Marking, the ability to quickly contextualize and adapt to the demands of an environment, and to hit the ground running, made him an overachiever with a fine, though far from world-class, team at his disposal.
This swift success elevated the former Borussia Dortmund head coach to one of the most unequivocally adored, admired, and respected figures ever to be associated with Chelsea.
Unfortunately, Thomas was sacked less than 19 months after his arrival, a decision which rightly astonished and shocked the majority of the fanbase.
Although he never had the luxury to relish something resembling to the backing in abundance provided to Pep Guardiola at Manchester City, both in quantity and quality or his German compatriot’s – Jurgen Klopp – level of data-led, highly qualified recruitment support at Liverpool, he turned water into wine more often than not.
Under his management, Chelsea reached as many as 6 finals in 18 months, winning the UEFA Champions League for the second time in their history, the UEFA Super Cup and The FIFA Club World Cup, whilst extremely narrowly missing out on three other pieces of silverware.
Tuchel’s dignity stretches well beyond the professional aspect of the job. In the spring of 2022, the footballing institution went through one of the most critical periods imaginable, not least in modern football, with ownership changing hands for the first time in 19 years.
Even though there was too much inevitable controversy, noise, and an immense scale of pressure surrounding Cobham, he never gave up, nor did he seek to find excuses, but carried on representing the club with utmost authenticity, transparency, honesty, and a great deal of capability to put himself in fans’ shoes.
1 – The Special One: Jose Mourinho
Could it have been anyone else? The suited 41-year-old, already a Champions League and UEFA Cup winner, presented himself as the new Chelsea FC manager in style, calling himself “a Special One.” He promised glory, and glory was to materialise. In other words, “he did exactly what he said on the tin.”
The end of 2004-05 saw Chelsea with 29 wins and only one loss. The Blues earned 95 points, five more than Arsenal’s Invincibles a year before. A mind-blowing record of only 15 goals were conceded, open play and dead-ball situations of all types included.
A shiny 4-3-3, rampant and extremely effective counterattacks were backed by a rearguard as strong as steel. Aided by Peter Kenyon, Mourinho constructed one of the most consistent squads in the Premier League Era and beyond.
A cocktail of ages, nationalities, strengths, cultures, planes of talent and so on, got together in West London for a common mission: to send Chelsea to the Olympus of English football.
They did so in fashion – not once, but twice on the spin. The duopoly of Manchester United and Arsenal had taken a considerable hit.
Two Carling Cups, one FA Cup, and a Community Shield were also added to the cabinet.
In relative terms, Mourinho’s second stint in charge was much more lukewarm than his first one, mainly due to some rough diamonds being let go extremely abruptly. Yet, another Premier League title and League Cup were brought home.
Through his immense skills in various areas of management, such as fostering a winning mindset, understanding human psychology, and building media relationships, this former assistant and translator to Sir Bobby Robson and Louis van Gaal cemented his status as one of the most decorated managers in football history.