John Terry is the prototype Chelsea player, but he could have been winning trophies for another Premier League big-hitter in his prime.
Back in 2009, Chelsea were three seasons without a Premier League title after going back-to-back in 2004/05 and 2005/06 under Jose Mourinho.
They were perennial contenders, finishing in the top three in each season after, but were struggling to get over the line.
John Terry reveals £29m offer from Man City in 2009
In September 2008, Sheikh Mansour took over as owner of Man City and started on a path that would eventually lead to complete domination of English football.
That goal might have been met much sooner if City got their way with Chelsea’s captain.
Speaking to Livesport Daily, Terry recalled the approach he was told about when he was preparing to sign a new contract at Stamford Bridge.

He reveals: “I know Man City made a 29 million pound bid for me back in 2009/10 when Ancelotti was the manager. And as soon as Chelsea spoke to me about it, I was like, ‘I don’t want to leave. I do not want to leave this football club. And if you want to sell me, then we have to have a different discussion because I don’t want to be here if you don’t want me.’
“And Roman was like, ‘We want you. We want you to stay.’ And I was like, ‘Well, 100% I want to stay, so let’s do a new contract.’ And I signed a new contract, committed the rest of my career really to Chelsea and signed a five-year contract at the age of 29, which was the best decision ever.”
A great decision indeed, though not all that surprising considering the love he has for the club. Terry even wants to manage Chelsea one day.
The Blues would win the domestic double that very season and the Champions League just two years later.
Terry could have accelerated City’s rise even further
Manchester City have enjoyed remarkable success in the years since that near-transfer. They lifted the Premier League title in 2011/12 and again in 2013/14, with Chelsea emerging as their main challengers during those seasons.
Had the former Chelsea captain made the move to the Etihad, the entire landscape of the early 2010s could have looked very different.
Terry is widely regarded as one of the greatest centre-backs in football history, and his presence would have raised both the floor and ceiling of any team he joined. If that deal had gone through, City’s era of dominance might have begun even earlier.
Instead, their sustained control of the Premier League only truly took off after the Chelsea icon retired from the game.
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