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Roman Abramovich's relentless pursuit of success has seen him chop and replace a number of managers in his nearly two-decade spell at Chelsea. The revolving door of managers sees a list of luminaries including Jose Mourinho, Carlo Ancelotti and Antonio Conte. They have all won Premier League crowns with Chelsea.
Unlike most clubs that have leniency and tolerance for long-term planning, Chelsea's impatience has been an extremely successful strategy. This has catapulted the club into one of the greatest modern European powerhouses.
Currently, with Thomas Tuchel, the Chelsea team look like a force to be reckoned with. They have already won a Champions League title last season. They are now looking to repeat that achievement while also adding the Premier League title to their name.
Amongst the many managerial appointments made, here's a look at the
5 worst Chelsea managers of the Abramovich era
#5 Rafa Benitez
Perhaps the most famous "interim" appointment of all time, Rafa Benitez's legacy at Chelsea is filled with animosity, acrimony and impatience. He joined Chelsea in the 2021-13 season.
Benitez stepped into a Chelsea team that was adrift of the Premier League and was unceremoniously knocked out in the Champions League. But he did a commenable job of steering the ship to safer shores, winning the Europa league and finishing third in the Premier League.
Having been Liverpool manager, Benitez was often at loggerheads with Chelsea and their fanbase. This made him seem like a cold and unassociative figure to fans, despite possessing admirable tactical nous.
His failure to lead Chelsea to their first ever Club World cup title is seen as a big black mark against his reign. He also reportedly had fallout with Abramovich. He he was unceremoniously cast aside in favour of the return of Jose Mourinho.
#4 Frank Lampard
He is arguably an extremely harsh entry on this list considering he performed his job at a dark time for the club in a transfer embargo. But Frank Lampard is still the statistically worst Chelsea manager of the Abramovich era, averaging just 1.67 points-per-game in the Premier League. Still, the legacy of blooding the likes of Reece James, Mason Mount, Tammy Abraham and Fikayo Tomori will always be fondly respected and remembered by all at the club.
The Chelsea club legend and all-time top scorer was seen by many to have made the jump to one of the biggest jobs in world football far too soon. He had just a single season's worth of experience with Derby County before. The Chelsea board still took a leap of faith as he was announced with great fanfare.
A single full season in the Premier League saw him finish 4th, just enough to qualify for the Champions League next year. Chelsea won the competition, albeit without Lampard at the helm, as he was sacked in January 2021 after a stuttering start to the 2020-21 season.
#3 Luiz Felipe Scolari
Scolari signed for the Blues in 2008. The former World Cup winning manager endured a disastrous spell in 2008-09 where he did not last through the season.
After just seven months in charge, Scolari was ousted despite going the first twelve games undefeated. He also reached the final stages of the Champions League and FA cup, before enduring a painful run of just three wins in nine Premier League games
"Big Phil" Scolari joined Chelsea in a summer which saw the likes of Deco and Ricardo Quaresma come in
He had publicized fallouts with Michael Ballack, Nicholas Anelka and Didier Drogba. He also famously had to use a translator to convey tactical and management advice. Due to these reasons, Scolari was on the chopping block as Abramovich demanded success.
In came Guus Hiddink, who lost just one game in 20 to lead Chelsea to the 2009 FA Cup. He was narrowly pipped by Barcelona and Manchester United in the Champions League and Premier League respectively.
#2 Andrea Villas-Boas
Young Andre Villas-Boas was brought in as a "chosen one," in 2011, having had a Chelsea connection since he was part of Jose Mourinho's backroom staff.
He went on to replicate Mourinho's success at Porto by winning the Europa League the previous season. This led to his appointment in 2011, despite being younger than some of his players.
Carlo Ancelotti was almost cruelly sacked after a disappointing second place finish and Champions League knockout against Manchester United. In came Villas-Boas with the hope of delivering the holy grail Champions League trophy.
Few would have predicted that Chelsea would deliver on that promise in his very first season. Though it was without him as manager as he was sacked halfway between the campaign.
When he arrived he shook things up at the club. He made personnel and tactical changes such as playing a very high defensive line and leaving club captain John Terry on the bench.
Roman Abramovich yearned for attacking football. However 10 lossess and 11 draws in his 40 games led to disarray at the club. Famous 5-3 losses to Arsenal, 3-1 to Napoli and 1-0 at home to West Brom turned out to be the final straw for the young Portuguese manager.
#1 Roberto Di Matteo
It is hard not to grant credit to Roberto Di Matteo's legacy of being the first ever Chelsea manager to win the Champions League.
He was signed in March 2011 after the sacking of Andre Villas-Boas.
He had the miraculous achievement of leading Chelsea through its greatest moment. Despite that, he is often considered the worst manager Roman Abramovich has taken on at the club based on his inexperience.
Di Matteo won just 24 games out of his 42 in charge, scoring a mere 43 goals, and looked considerably out of depth in a tame Chelsea set-up. He had Fernando Torres and Daniel Sturridge as the only two recognized strikers in the squad.
The disastrous 3-0 defeat against Juventus was where he publicly dropped Fernando Torres at centre-forward. He went with Eden Hazard as a false nine. The defeat signaled the end of the line for the still fondly loved and respected Italian.
