This summer, for the first time, the former England international was without a contract, looking for employment.
At 36 years old, definitely past his peak, Terry has opted to drop into the Championship to join ambitious Aston Villa in a deal reportedly worth £4million a year.
Yet, a swansong in the Championship, with less than average forwards looking to get one over on the Premier League legend, doesn't feel like a fitting end to a glittering career for the former England captain.
Seven hundred and thirty-seven Chelsea appearances. 17 trophies lifted. 78 eight England caps. These aren’t the numbers of your average Championship player. But that is exactly what Terry will be next season.
Last season, as Antonio Conte's men romped to the title, Terry managed just six Premier League appearances. So it should be no surprise that teams from the top flight weren't falling over themselves to sign the 36-year-old.
Away from the footballing side, picking up the former Chelsea captain would give any club a publicity boost, and many would be tuning in to see how he copes, especially if he does make the drop down to England's second tier.
Yet is isn’t. Perhaps they saw some of Terry’s displays last season. He looked every one of his 36 years, most notably in the win over a hapless Watford side who somehow scored three against a mix-and-match Blues line-up days after clinching the Premier League title.
Terry was all at sea that evening at Stamford Bridge, his poor decision making exposed as he was no longer able to make up lost ground and Étienne Capoue was able to level for the visitors at a time when they’d barely had a sniff. At that moment, Conte's decision to let Terry go looked justified.
There is little doubt that Terry no longer has the ability to perform at the highest level. His mobility, which often saved him, no leaves him vulnerable in a back four. His days of playing twice a week, something key to life in the Championship, are well behind him. He would only be of use performing the Ledley King role of playing when able and putting his feet up in the week.
Your legs may go, your body will hurt, but that doesn't mean you lose pride. A fierce competitor until the very end, Terry for 19 seasons has put his body on the line. Yet, now, the fire might still roar in the belly, but his body can't match the fight. It would be sad to see someone who has achieved so much, struggle throughout next season.
There is previous that suggests the path Terry is taking rarely works out. When Rio Ferdinand traded Manchester United for Queens Park Rangers in his final season as a pro he went from a glistening Rolls Royce of a defender to a written-off Vauxhall Corsa in the space of 11 games.
Without the talents of Nemanja Vidić, Patrice Evra and Real Madrid transfer target David de Gea around him, Ferdinand’s decline was accelerated and a fine career ended on the substitutes’ bench at Loftus Road with the R’s relegated.
Teddy Sheringham did similar, signing for Championship minnows Colchester United as a 42-year-old after leaving West Ham United. However, injury ended his career ‘prematurely’ in 2008 after just 11 league outings and three goals for the U’s.
Robbie Fowler, a legend at Anfield, tried in vain to prolong his career with spells at second-tier Cardiff City and Blackburn Rovers. In two seasons, he managed just four league goals, a far from fitting ending for the man Liverpool fans called ‘God’.
Perhaps the centre-back will see sense from the mistakes made by his peers and look to bow out with dignity, preserving his one-club-man status – ignoring his loan spell at Nottingham Forest.
There will surely be TV and other media organisations desperate to add Terry to their roster. Hard to imagine that job opportunities won't come his way, it just takes a strong character to make that final decision to hang up his boots.
This has been a season of retirements with Bayern Munich pair Philipp Lahm and Xabi Alonso calling time on glittering careers. Like Terry, neither man had anything to prove and little need, financially, to play on. Serial winners on the club scene, each has a World Cup winners’ medal to boot. Both were afforded gracious and warm send-offs by the Bayern supporters and will be remembered as classy servants for the Bavarian giants.
You wouldn't see them dropping down to the Bundesliga.2, just to play another year.
The last memories Terry should have of his playing career should be saying goodbye to his adoring fans at Stamford Bridge with the Premier League trophy in hand. Not getting beat down the channels by some teenager on a cold wet Tuesday night in Barnsley.