5 Biggest Mistakes by Roman Abramovich at Chelsea

Roman Abramovich is credited with reinventing Chelsea into the European powerhouse they are today. While the club is notorious for big splurges and sacking many a manager, it has inherited a sense of community and prosperity despite the ruthless pursuit of titles and victory under Roman Abramovich.

Mistakes made in Roman's Reign

Despite their immense enviable success, there are many mistakes that have been made over the last 18 years of Roman Abramovich's patronage at Chelsea. Here are five of the biggest mistakes that will go down in history.

5. Sacking Carlo Ancelotti

Carlo Ancelotti's tenure at Stamford Bridge proved to be immensely popular with players, fans and management alike. An inspiring father-like figure who has gone on to have arguably the most diversely decorated career of any modern day football manager, Ancelotti was the perfect match for Roman Abramovic's hefty expectations.

Ancelotti operated with a sense of trust and faith in his players, with the squad in his two seasons boasting the likes of Didier Drogba, Petr Cech, John Terry, Michael Essien and Michael Ballack, all of whom were not just superstars but national captains.

On a tactical front, the attacking 4-3-3 and at times 4-4-2 diamond provided Chelsea with some of the most attractive attacking football Stamford Bridge had seen up to that point, securing a historic double in 2009/10.

The unfortunate fallout in the subsequent 2010-11 campaign came on the back of a second-place Premier League finish to Manchester United. An unceremonious Champions League semi-final defeat to the Red Devils led Chelsea to endure a trophyless season. At a time when Roman Abramovich was obsessed with the Champions League trophy, a league title or domestic cup was considered as a minimal par, which Ancelotti fell just short of.

4. The Purchase of Fernando Torres

Chelsea Press Conference to announce new signing Fernando Torres

Closely tying with #5, the purchase of Fernando Torres is a controversial addition on this list , in consideration of the Champions League and Europa League titles won in his time at Chelsea. Despite the accolades, the general consensus is that Torres was a huge disappointment at Chelsea and was a poorly timed transfer for a player past his prime. Bought for a jaw-dropping 50 million pounds in January 2011, Torres looked a pale shadow of the clinical and stylish striker who played for the Reds in Liverpool and Spain. Struggling for form fitness, his four-year sojourn at Chelsea saw him lose confidence and question his own ability. Many Chelsea fans saw him as a liability, wasting clear cut chances that his predecessor Didider Drogba thrived on. The hefty price tag also put pressure on managers to select him in the team at a time when the alternative options on the bench seemed better placed, a lesson Roberto Di Matteo harshly learned in his final game in charge where Eden Hazard was deployed as a central striker over Torres, the resulting loss costing him his job.

3. Sacking Jose Mourinho in 2007

Chelsea Training & Press Conference De Bruyne, Lukaku and Salah in Chelsea colours

Chelsea fans will tell you that one of the darkest days of the Abramovich era was the day it was announced that Jose Mourinho had been sacked as manager in September 2007. Jose Mourinho's acrimonious departure from Stamford Bridge was one of the biggest shocks in the club's history, having expected the "Special One" to lay a long-lasting legacy. The manager, who had just led them to two back-to-back domestic league titles, an FA Cup and a League Cup, found himself on the chopping board after a continuously strained relationship with management and players.

As has become known now, Mourinho operates with a sense of tension and drive, which all too often becomes far too much for the clubs he stays at. The Special One was particularly critical of the signing of Andriy Schevchenko, a favorite of Mr. Abramovich, creating a strained relationship between owner and manager that reflected in poor results on the pitch. A reunion in 2015 giving another League Title and Cup glory, was unfortunately not enough for history to repeat itself with Chelsea and Mourinho, and a chance at a dynasty like Sir Alex Ferguson went unrealised.

2. The Sale of Lukaku, De Bruyne and Salah

The Chelsea set-up has often been criticized for the vast number of players on their books, constantly going out on loan and treated as a mere financial asset by the club. That being said, Chelsea's scouring network and youth academy was a considerable focus point for Abramovich besides the superstar signings, attracting a number of world class talents at a very young age. Amongst the many who have been on Chelsea's books, no three players stick out more than Romelu Lukaku, Kevin De Bruyne and Mohammad Salah who have gone on to become arguably the best players of their generation, albeit never enjoying success in a Chelsea shirt.

Romelu Lukaku was heir apparent to Didier Drogba, but the shadow of the Ivorian legend was far too heavy to grow out of, forcing loan moves to West Brom and Everton which led to his eventual departure. De Bruyne and Salah were seen as squad players getting very limited game time and were not given the time to mature into the incredible players they are today. A large part of the blame for the lack of patience comes from the very top, with Roman Abramovich demanding trophy after trophy, with little room for blooding youth.

1. Failure to promote Academy players

Arsenal v Chelsea - FA Youth Cup Final: Second Leg

At the time of writing, Chelsea are by far the most successful youth team in England since Abramovich took over the club. Multiple FA youth cups and tourneys have unfortunately meant very little to the hierarchy at Stamford Bridge who until very recently were reluctant to promote youth prospects. Josh McEcharan, Gael Kakuta, Dominic Solanke, Lucas Piazon and Nathaniel Chalobah are a few names that disappointingly stand out for failing to make the grade. All the above names and many more came with a huge reputation that they failed to translate to the highest level.

While there was no question of their ability, they were given just a few opportunities in the first team, where the pressure and expectation to deliver from the get-go at an immensely competitive club like Chelsea was simply too much for many talented starlets. With Chelsea's legendary captain perhaps the only modern day great homegrown talent, fans have been itching to have an academy graduate in the first team much like Manchester United and Liverpool pride themselves on.

Thankfully, the inconvenient circumstances of the transfer ban in 2019/20 forced Chelsea's hand to promote many first team talent such as Callum Hudson Odoi, Ruben Loftus Cheek, Tammy Abraham, Mason Mount, Reece James and Fikayo Tomori, all of whom have begun with a degree of success and promise that the prior generations lacked. Sadly, at the time of writing, the summer of 2021 saw another mass exodus of promising academy players such as Marc Guehi, a disappointing indication of a continuing cycle.