As far back as May, rumors were rife the Turkish giants were eager to reunite him with former Blues teammate Didier Drogba—the Daily Mail going so far as to suggest a contract worth £30 million would be offered in a bid to tempt him away from Stamford Bridge.
And now, Roberto Mancini's apparent interest has resurfaced, with Galatasaray's Italian manager reportedly eager to make a move in January, according to The Mirror.
Struggling for form and a place in the Chelsea line-up in the latter stages of 2012-13, Terry would have been forgiven for thinking a change of scenery was ideal. He seemed to be at a crossroads in his career and, for the first time, was unsure of what the future held, having been in the Blues' first team for 14 years.
In that time, he has won every major honor possible, but things looked bleak for Terry under Rafa Benitez, who had marginalized him. Terry was no longer the leader he had been for the previous decade, and his position wasn't under threat—it had been taken.
From cutting a frustrated figure on the sidelines, the return of Jose Mourinho this year has galvanized Chelsea's captain, however. He has started every one of the Blues' Premier League matches and is proving an essential figure in their hunt for silverware.
Indeed, Terry is enjoying the type of form that has raised questions as to whether England manager Roy Hodgson should endeavor to tempt him out of international retirement ahead of next summer's World Cup.
It's over six months until Hodgson will have to announce his squad, of course, but that Terry is being mentioned in such conversations is confirmation of how dramatically his fortunes have changed.
So, why take a backward step by moving to Turkey should Galatasaray act upon their interest? Financial reasons aside, Terry would be giving up so much more were he to travel east, namely his Stamford Bridge legacy.
We need only look to Francesco Totti and his exploits at Roma this season to understand the value in remaining true to your colors.
The Italian has been among the elite of his generation. At the peak of his career, he had the choice of joining any of Europe's leading clubs. Yet, he stayed loyal to his roots, and now, in the twilight of his days as a football player, the wisdom of his choices are being seen.
This year has marked a renaissance for Totti and his club under the guidance of Rudi Garcia. Roma top Serie A having won their first 10 matches, drawing just twice. Totti has been a big part of that.
His legend has long been secure, yet his loyalty acts to make it stand apart. He is Roma, representing everything the club stands for and is worshipped by the fans.
That Totti has remained to feature so prominently in their remarkable season only adds to the romance of it all.
Terry's reputation in West London is much the same. His "Captain. Leader. Legend." banner is still proudly displayed at Stamford Bridge come matchday, his name sung with gusto.
Moving to Galatasaray would end that. Chelsea fans wouldn't turn their back on him, but the sight of him in anything but a blue shirt would give rise to an unnerving feeling. Where have all the heroes gone?
It shouldn't be about money for Terry—he's earned enough in his career, after all. No, it's about making a stand, setting an example in age where cynicism has long overruled the romance of football.
Terry has been criticized for many things, his character judged and personality undermined. Now's his chance to prove it's all been on the contrary.
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