The Blues skipper is reportedly close to putting pen to paper on a one-year deal, just a few weeks after it was initially reported he was harking for more than the 12 months on offer, something that has become policy in recent years for the club to offer players the wrong side of 30.
The Daily Mail reports Terry will have his new contract signed, sealed and delivered sooner rather than later, which will be welcomed by fans given the form of their captain this season.
The Englishman is looking rejuvenated right now, enjoying his finest spell in a long while and has proved influential at the heart of defence. Given his aging years, however, it can't be too long before he begins to turn his focus onto the possibility of becoming Chelsea manager.
He will have a fight on his hands, if that proves to be the case. Jose Mourinho has already said this season that he would like to remain at Stamford Bridge for some time yet, building a dynasty not too dissimilar to what Sir Alex Ferguson has created at Manchester United.
Terry himself has made no secret in the past of his desire to one day take over the Stamford Bridge reins.
"Obviously my overall aim is to become manager," he told The Mirror in July 2011.
When considering his leadership qualities on the field, it's not hard to imagine Terry in the dugout, barking orders from the sidelines.
For the best part of a decade he has been the man Chelsea has revolved around—representing everything the club stands for.
But that's John Terry the player. What of John Terry the man?
Whereas a captain can lead from the front and inspire his team-mates, the task of a manager is somewhat different. He remains a leader, but must bring his players together, control and unite them as one—an ability it's unclear if Terry has in his repertoire.
It's one thing doing it as a player; it's quite another doing it as the man who is responsible for a whole lot more.
The 33-year-old has proved a divisive character at times. Whether it is rumours of extra-marital affairs with the former partners of ex-team-mates or attempting a very public coup of the England dressing room during the 2010 World Cup, he has often split opinion.
To Chelsea fans he is a hero and will remain so regardless of where the remaining years of his playing career take him. For his fellow professionals, it is far from the case.
Terry's experiences at Chelsea will have shown him how easy it can be for a manager to lose the faith and backing of the players in the dressing room. When that happens, it proves futile.
Indeed, outside of Mourinho, there have been some major casualties at Chelsea in the Roman Abramovich era.
Avram Grant and Luis Felipe Scolari struggled to get the players behind them and each lasted less than a year, while more recently Andre Villas-Boas' relationship with key personnel also saw him shown the exit door prematurely.
It's a factor that carries much weight in the modern era. It's what makes Mourinho so great.
The Portuguese has shown time and again that he has the tactical nous to outwit his opponents—he did just that on Monday evening against Manuel Pellegrini and Manchester City.
Where he excels, too, is his relationship with the players. Mourinho has everyone playing for him, buying into his philosophy. It's a factor that proves just as successful as the tactics he opts to deploy as, without his players behind him, he knows success will be impossible to achieve.
How will Terry do that at Chelsea or any other club for that matter? Will his baggage as a player roll over to his managerial career? It's a valid question and the answer will determine whether he repeats his success as a player in the dugout.
Just as his achievements will haunt the player who eventually replaces him in defence, the ghost of Mourinho will always be lingering in the background for Terry.
Terry is the benchmark for what Chelsea fans expect from their defenders and Mourinho is the same when it comes to their managers.
If he ever emulates his current boss by taking up the Stamford Bridge hot seat, he'll do well to bear that in mind.
Garry Hayes is Bleacher Report's lead Chelsea correspondent and will be following the club from a London base throughout the 2013-14 season. Follow him on Twitter here @garryhayes