This interview was created as part of 'The Big Pete', a multimedia project by Flashscore and CANAL+ Sport set to launch in spring 2026.
Terry, who won the Champions League, the Premier League as well as domestic cups with the Blues, played 492 times across 19 seasons at Stamford Bridge in the heart of the defence.
After retiring in 2018, the former England international plied his trade in the dugout, taking up a coaching role at Aston Villa under Dean Smith.
Along with a stint at Leicester City, he has since returned to Chelsea on a part-time basis, taking on a video analysis role.
However, it has been over four years since his time coaching at Villa Park, and he admitted to Livesport Daily that if you are not moving forward in the competitive world of football, then you can be left behind.
Speaking about his future in football, Terry explained: "I kind of spent three years at Aston Villa, where we got promoted back to the Premier League, and then I was in search of a job myself as well, but didn't get the opportunity to go and coach or go and manage a football team.
"So I spent two or three years after I left Aston Villa working really hard, trying to find that role, and was unable to find a job. So, (there is) nothing more I can do, really, other than kind of just try and enjoy my life now. And I think I searched for a couple of years to try and find a role within football, and unfortunately, nothing that kind of ticked my box and made me happy.
"I've probably been out of it for too long now. So it's been, what, four years since I left Aston Villa coaching. And for me, I think if you want to be a top coach or a top manager, you have to keep your finger on the pulse and you have to be watching everything. You have to be obsessed with that.
"...My dream is to manage Chelsea, but without all the other stuff, that dream probably doesn't become a reality. I'm happy with what I've achieved at Chelsea in my playing career and captaining the football club, but the latest one probably doesn't happen."
Despite the reality of his current plight, Terry still has plenty to hang his hat on, and nothing is as big in club football as the Champions League.
After missing the decisive penalty during the 2008 shootout against Manchester United, he was able to exorcise those demons four years later when the Blues shocked Bayern Munich on their own patch.
Terry missed the final due to suspension, but it didn't mean that he was unable to make headlines...
"I had my full kit. Do you not remember?"
He continued: "It's a funny one actually, because people ask me my best moment in a Chelsea shirt, or in the history of the club. For me, it's the game I didn't play in 2012.
"And when you've been at a football club for so long, you understand how important it is to the supporters and to the people within the football club, and to the players as well.
"We worked so hard over the years to win that trophy. It's the most difficult trophy I've ever tried to win. And in a game when we were probably the second favourites, we're in Munich, playing against Bayern Munich, in their stadium, in their city.
"Pete (Petr Cech) saves a penalty, the shots he saved, Didier scoring late on when we're all a little bit older as well.
"In 05/06, 09/10, when Barcelona scored very late as well, we were probably the favourites to go on and win it. In the year that we were an ageing squad and we were coming towards the back end of our careers, someone decided that we're going to win the Champions League.
"We had some top players in the group as well, but also, you need a little bit of luck along the way, and I think we had that. So for me, the best moment, just seeing the people that I played with and how much it meant to the players, and also the supporters as well."
England's underachieving 'golden generation'
Despite a club career that was full of success, it was not replicated on an international level. Terry was part of the so-called 'golden generation' with England that included the likes of Rio Ferdinand, Steven Gerrard, Paul Scholes and, of course, David Beckham.
With the Three Lions, he was unable to make it past a quarter-final at a major tournament, something that still haunts him to this day.
Asked whether he knew why they didn't want any titles, he said: "I don't know why. I've heard other players come out and say their reasons why.
"I didn't feel the same as what those other players felt. I didn't feel the rivalry within those dressing rooms, and sitting there, with the Man United players, the Liverpool players. I went in there and tried to be that... tried to be everyone together. Maybe the rivalry between Liverpool and Man United was too fierce."
Gerrard is one of those players who has had his say on that time, labelling them as 'egotistical'.
Answering back to those claims, Terry mused: "It's actually really good because it's something that we haven't spoken about as players. It's not like we sit there and speak about this, whether it's Frank (Lampard) having his opinion or Stevie or Rio or somebody else having their opinion, Paul Scholes having his opinion, and everyone's entitled to their opinion.
"(It) doesn't mean to say I have to sit here and agree. I can only explain to you how I felt in those moments. And I felt like when I was with England, I was an England player. I wasn't a Chelsea player."
The current crop of England players have also yet to win anything. However, they have made two European Championship finals as they move closer to breaking their nearly 60-year drought without a major trophy.
Three Lions' chances at the World Cup
Speaking after England qualified for the 2026 World Cup with a perfect record, Terry added: "It's probably the best opportunity that we're going to have.
"I think currently, we have a really good squad of players, a mixture of young players, experienced players like Harry Kane within the group, Harry Maguire, John Stones, mixed with these young talented players in Phil Foden, Cole Palmer, Jack Grealish, and Jude Bellingham.
"These guys have that rawness about them to feel no fear when they go into games as well. So, I think we have a real opportunity."
During his full chat with Livesport Daily, Terry also touched upon the pressures of the Premier League, the best player he ever played against and leading a successful club. Watch the full interview below!
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