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#3 Signing Andriy Shevchenko
A signing that must have hurt Roman Abramovich is the 2006 acquisition of striker Andriy Shevchenko. The club had tried to sign the striker for almost a year before they eventually got their hands on the 2004 Ballon d'Or winner.
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Shevchenko was reportedly swayed to sign for Chelsea by his personal relationship with Abramovich, who was ready to pay as much as possible for the striker's services.
Chelsea paid €48.9 millon for the 30-year-old striker with Jose Mourinho as manager. Shevchenko played under Mourinho and Avram Grant before he was deemed surplus to requirements by Luiz Felipe Scolari. He returned to AC Milan on loan in 2008 afterwards before returning briefly at the start of the 2009-10 season before his eventual sale.
Shevchenko scored 22 goals in 77 appearances for Chelsea. His goal tally was nowhere near good enough for Chelsea, considering that he was signed for an English record fee. Like a lot of other strikers, Shevchenko struggled a lot in London and failed to settle in.
#2 Failing to build a stadium
As Roman Abramovich leaves Chelsea, he leaves the club without its own stadium. The club have used the Stamford Bridge stadium almost throughout its history, but it does not own the stadium.
Upon the recognition that a club of Chelsea's pedigree needed a bigger stadium of its own, plans were put in motion in 2014 to build a befitting one. In 2017, London Mayor Sadiq Khan approved of plans to build a 60,000 capacity stadium, but the plug was pulled on the deal when Abramovich's troubles began in 2018. The oligarch withdrew his application to renew his investor visa after delay in the processing of it in light of diplomatic tensions between London and Moscow.
Chelsea planned to finish the stadium in 3-4 years, but decided against embarking on the project when Abramovich was denied access to the country.
According to early reports, potential new owners are reducing their valuation of the club due to the state of its stadium. This may ultimately cause the club to be sold for a lower amount than the asking price.
#1 Firing Carlo Ancelotti
Former AC Milan boss Carlo Ancelotti was appointed as Chelsea's manager in 2009, replacing Guus Hiddink at the helm of affairs at Stamford Bridge. The Italian enjoyed a good deal of success at the club but was sacked to the surprise of even Chelsea fans.
Ancelotti took over Chelsea in the 2009/10 season and immediately led his side to Premier League glory, becoming the first side to score 100 goals or more in Premier League history. He also secured the FA Cup to give Chelsea its first-ever domestic double. He got the best out of Didier Drogba, Nicolas Anelka and other attacking players at the club. In his second season in charge, he led Chelsea to second place behind Manchester United. Ancelotti was sacked mere hours after the final match of the 2010-11 season.
Ancelotti's sacking came as a huge surprise. After his initial success with the club, no one expected the club to let go of him quickly.
