Chelsea's captain came close to a move to City in 2009 but now, at 33, he has adapted his game and played every minute of Chelsea's Premier League campaign.
Every career is studded with ifs, buts and maybes but John Terry could have been leading out Manchester City, and not Chelsea, at the Etihad Stadium on Monday night in the fixture that might define this Premier League season and his future.
It is easy to forget just how close Terry was to quitting Chelsea in 2009 when he appeared to be conducting negotiations with City himself over a £30 million transfer – rather than using his then agent Aaron Lincoln who he split with later that summer after pledging his future to Stamford Bridge.
Terry, somewhat implausibly, later insisted he never had any intention of leaving and said a new contract and a pay rise was not a priority. He also spoke with authority about his relationship with Roman Abramovich and the fantasy signings Chelsea needed.
Terry then signed a five-year deal that, at that time, made him the Premier League’s highest-paid player earning £150,000 a week. He was at the height of his powers, his influence, his importance. He was the captain, leader, legend; for club and for country.
As ever with Terry it gave him a dangerous sense of invincibility.
That deal, enhanced by City’s interest, expires this summer. The last contract was hailed as one which would mean Terry would see out his career at the club he joined as a 14-year-old and was greeted with a statement by Chelsea that read: “This reaffirms both John’s and Chelsea’s long-stated desire for him to be at Stamford Bridge for the rest of his playing career.”
The intervening years have been turbulent on and off the field: from the alleged affair with Wayne Bridge’s then partner Vanessa Perroncel, the World Cup debacle, being convicted of racially abusing Anton Ferdinand, to being stripped off the England captaincy not once but twice and retiring from international football.
There have been a series of high-profile, career-threatening crises that have eroded his status at Chelsea and coincided with the waning of his powers as a player.
It seemed that Terry was being ushered out. Not by Andre Villas-Boas or Roberto Di Matteo but certainly Rafael Benítez who took the cold-eyed view that the 33-year-old was physically unable to cope with two matches a week and was struggling.
When Terry was being courted by City, Chelsea were on tour in the United States; when they toured America again in 2012 under Di Matteo his standing at the club – which he had occasionally treated as if he ran – was not the same. He seemed less certain, which Jose Mourinho later identified as a loss of “self-esteem”.
Now Mourinho can, with reason, agree when he is asked whether on current form Terry is the best central defender in the Premier League.
Vincent Kompany, who will lead out City instead of Terry, is his nearest rival to that claim but injury problems have hampered the Belgian this campaign. Once again Terry has defied his critics. At times, he has defied logic and reason.
Terry, remarkably, has played every minute of every Chelsea league match and has looked assured.
He has already made more appearances this season that in the whole of last season (30 compared to 27) as he has reached an impressive 604 games for the club where he is still the last player to break through to the first-team from the youth set-up.
It sets up the intriguing prospect of Terry marshalling Chelsea’s defence – although presumably not relying on “19th century football” – against City’s apparently irresistible strike-force. It is the kind of backs-against-the-wall scenario he has relished in the past.
The stats are incredible, of course. City have scored 68 goals in 23 league matches (Chelsea have 25 fewer); have scored at least three goals in 23 of their 37 games in all competitions; they last failed to score on November 10; they have only failed to score twice in those 37 matches and, if anything, their rate of scoring is increasing: their last seven matches have gone six, two, five, four, three, four, five in terms of goals scored, while the Etihad Stadium has become a free-scoring fortress.
There are two stats where Chelsea can claim superiority: they have conceded the fewest goals in the league (20) and have more clean sheets overall than City with 17 compared to 14. There is another – they beat City at home, 2-1, and there is that Mourinho mentality of not losing to the other top teams having already drawn away to Manchester United, Arsenal and Tottenham Hotspur. How he would relish another clean sheet.
In the first two of those games Chelsea did not concede, against Spurs, it was Terry who scored their goal in a fiercely contested 1-1 draw – a trademark header from a free-kick – and there is no doubt he has regained his impact under Mourinho even if he understandably has also modified his game with age.
Always underrated as a football player – Terry is a good passer of the ball, short and long, and an intelligent reader of the game – he has adapted the way he has played and is now much more the ‘free man’ who can drop off and organise rather than the stopper at the heart of the defence.
That has also helped him, to an extent, to mask his lack of pace which has always been a worry not least when Mourinho managed Chelsea the first time round and expressed his concern about the captain’s fitness problems and his form.
Terry also still hankers after an England return for the Brazil World Cup but that is unlikely to happen and the claim that he has been in text-message contact with the England manager has been met sniffily by Roy Hodgson. If the decision was based solely on form then Terry would be in Hodgson’s team.
Terry’s international exile suits Mourinho – even if he states otherwise – just as Sir Alex Ferguson took delight in Paul Scholes retiring from England duty.
Whether, like Scholes, Terry is still playing for the club where his career started and has endured at the age of 38 remains to be seen.
But on Monday he will fix that captain’s armband on his bicep, puff out his chest and lead Chelsea against City to try and again reaffirm his status as a remarkably resilient warrior.