Carlo Ancelotti is widely regarded as one of Chelsea's best managers of the modern era.
During his two years at the helm from 2009 to 2011, he guided the club to a historic Premier League and FA Cup double in his debut season, followed by a second-place league finish in his next.
Infamously, however, his achievements weren’t enough to satisfy Roman Abramovich, who ruthlessly dismissed him on the final day of the 2010/11 campaign.
Yet, had Ancelotti made a different decision in the transfer market, that season might have played out very differently.
According to journalist Simon Phillips, former Chelsea technical director Michael Emenalo wanted to sign David Silva in the summer of 2010, with the Spanish playmaker still dazzling for Valencia in La Liga.
Ancelotti, however, passed on the opportunity.
Silva, of course, went on to join Manchester City, where he became one of the Premier League’s greatest-ever midfielders, winning four league titles, two FA Cups, and five EFL Cups during a trophy-laden decade at the Etihad.
Chelsea would the following year go on to sign Silva's former Valencia teammate Juan Mata, somewhat Chelsea would go on to sign Silva’s former Valencia teammate Juan Mata the following year, somewhat softening the blow of missing out on the now-City legend.
Still, you can’t help but wonder how things might have turned out if the Blues had managed to bring both playmakers to Stamford Bridge.
Silva isn’t the only Manchester City legend Chelsea, and Ancelotti, missed out on signing.
According to former Blues midfielder Joe Cole, the club also passed on the opportunity to sign Sergio Agüero before his move from Atlético Madrid to City in 2011.
"Chelsea were after him," Cole told BT Sport, per the Mail Online, in 2021. "I think maybe they looked at his shape and passed on him at the time, which was obviously a mistake."
Agüero would go on to spend 10 seasons with City, scoring a club-record 260 goals and cementing himself as one of the greatest strikers in Premier League history.
Oh, Carlo.
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