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3. Sacking Jose Mourinho in 2007
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
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.
