There is a story about John Terry’s first day in coaching that demonstrates how the former England captain, Chelsea history-maker and serial champion was determined to make the leap from elite footballer to elite coach.

It goes back to his time at Aston Villa and the scene at their training ground when Terry rejoined the club where he had played the 837th and last senior game of his career. 

Those moments can be slightly awkward, when a player stops being ‘one of the lads’ to take a more senior role. Here, though, Terry’s former team-mates felt comfortable enough to poke fun at him for turning up in white boots. After that, Terry reverted to a more traditional black pair.

For the coaches, what struck them most was his enthusiasm. Terry’s career included 78 England caps, enough trophies to fill an aircraft hangar and a reputation as one of the greatest defenders of the Premier League era. Yet this was new territory for him, very much learning on the job. To everyone’s amusement, the new appointment turned up with a pencil case and notepad.

That was October 2018 and seven and a half years on, these would ordinarily be the moments to analyse Terry as a manager, tactician and motivator. That, after all, is why he went through all the coaching qualifications: to work his way up and become a ‘No 1’ in his own right.

It is why Terry used to store written training notes at home, going back to the day Jose Mourinho started at Chelsea in 2004. Those notes were kept impeccably, bound as coaching manuals, on the shelves in Terry’s study. It was a blitz of diagrams and detail, scribbles and squiggles, rondos and revelations. What did they show? That, even in his mid-twenties, he was meticulously planning to become the Special One mark II.

It has never worked out that way. Terry, now 45, has had to make do with a part-time mentoring role in Chelsea’s academy. Officially, he works two days a month, though he is often there much longer. It seems a nice life, interspersed with skiing trips, five-star holidays and testing his golf handicap on some of the world’s more luxurious courses.

Yet his role at Chelsea is not, by his own admission, the one he imagined for himself.

Terry may also have to accept that many observers will join the dots and wonder whether that is, in part, due to the various controversies that have shaped his professional life.

Would it have been any different if he had not caused so much damage, intermittently, to his own reputation? Might there have been bigger and better opportunities for a man with his otherwise exceptional CV?

Those questions multiplied after the recent blitz of headlines caused by Terry using his Instagram account to signal his apparent approval for a proposal by a radical right-wing political party for a nationwide ban on burqas in the United Kingdom.

Did he not realise it was going against Chelsea’s own inclusion policy? Had it passed him by that the club set up a Muslim supporters group last year? Or that the modern-day Chelsea, in the words of Piara Powar, one of the sport’s leading anti-racism campaigners, is “very much centring its identity on being a London club and everything that means”?

Powar, executive director of anti-discrimination network Fare, has told The Athletic that Chelsea could be entitled to instigate a safeguarding inquiry to investigate if Terry is “the right guy to be working with young people, if he is carrying these sorts of prejudices”.

Kick It Out, football’s biggest anti-racism organisation, has also felt strongly enough about it to speak publicly. Inside Chelsea, it has caused dismay.

In examining Terry’s failure to secure a more prominent role in the sport he dominated as a player, The Athletic has spoken to people with a direct line to him, including past and present colleagues, coaches and players. Many are speaking anonymously to protect work relationships.

Whatever your views, whatever your politics, their responses raise another significant question: is John Terry his own worst enemy?

What nobody should assume is that Terry has been starved of job offers.

Some of those offers have been with lower-league clubs that, in his eyes, could never suit his ambitions. At other times, he has been shortlisted for interviews without anything coming of it.

Terry has made it clear behind the scenes that he has no desire to do what Jermain Defoe has done with fifth-tier Woking and coach that far down the football pyramid. He always had his aims set much higher, as English Football League clubs have found out in recent years. But it is not the case that only Chelsea would hire him.

At Villa, for example, Terry ended up being part of the coaching staff and, at one stage, firmly in the running to be their new manager.

The idea came from Christian Purslow, then Villa’s chief executive, while the club were seeking a replacement for Steve Bruce. Purslow had previously been a commercial executive at Chelsea. He knew Terry from Stamford Bridge and added him to Villa’s managerial shortlist with Dean Smith, Thierry Henry and several others.

Although it was never a deal-breaker, Smith was asked during his interview whether he would be prepared to add Terry to his coaching staff. Smith agreed to take the job, but what Purslow and Jesus Garcia Pitarch, then Villa’s sporting director, did not realise was that the new manager already knew Terry from coaching his older brother, Paul, at Leyton Orient. Smith then interviewed Terry and agreed he would be a good addition, so they were both hired.

Behind the scenes, Purslow called Terry the “self-appointed king of high standards”, referring to the way he would push for hotel upgrades, better food and the little extras to make Villa’s players feel like they were at an elite club. Players have talked positively about his influence on the training ground — how, for example, he helped Tyrone Mings with his defending and coached Tammy Abrahams to be a better header of the ball.

Tyrone Mings benefited from working with Terry at Aston Villa (Naomi Baker/Getty Images)

“When he first signed, I had to pinch myself,” Jack Grealish, then 23, told reporters at the time. “He is so professional in everything he does and that rubs off on us young players. I will be thinking, ‘Do I need to be doing that?’ when he is doing it, because look where it has got him. Things like ice baths, massages and not going home after training straight away. He is always the last person here, eating properly and doing everything right.”

At Chelsea, where Terry has a consultancy contract, there are similar stories about him taking academy boys through video analysis and chatting to them about their development, providing a level of expertise and one-on-one insight that few players of that age would ordinarily get. Harrison Murray-Campbell, Chelsea’s 19-year-old defender, is one player who has benefited from Terry’s expertise since the five-time Premier League champion took the role in 2021.

Ultimately, though, it seems to be a fact of life for Terry that some kind of trouble, or controversy, is always around the corner. And it is usually of his own making.

One of those occasions came two Sundays ago when Terry logged into his Instagram account and saw a post from Rupert Lowe, the founder of Restore Britain, in which he stated his intention to outlaw the burqa, worn by some Muslim women, if his anti-immigration party ever came to power.

If you are not familiar with Lowe, he is the former Southampton chairman who went into politics with Reform UK before becoming the subject of a police investigation for alleged threats towards the party’s chairman, Zia Yusuf. The case was eventually dropped and Lowe, citing “false allegations” and a “brutal smear campaign”, formed his own party, deploying extreme anti-Muslim rhetoric and calling for a policy of mass deportation.

One of his social-media posts, liked by Terry, promises to “deport millions” and that “the entire power of the British state would be deployed”.

The post about the burqa included a picture of a London Underground station, Whitechapel, which had its name translated into Bengali as well as the original English version. “This picture was taken in London,” Lowe commented. “Restore Britain would ban the burqa and ensure all London stations use English. Enough is enough.”

Terry, raised in nearby Barking, responded with three applauding emojis and the national flag of England. His response was subsequently deleted.

Should it matter? Simon Jordan, the former Crystal Palace owner turned radio pundit, made the most voluble case on Terry’s behalf, using his platform on Talksport to argue that people in football should be free to ‘like’ a politician’s opinion without it being jumped upon.

“Liking that (post), and agreeing with that, doesn’t leap into him agreeing with every other thing Rupert Lowe says,” said Jordan. “I agree with lots of things Keir Starmer says. I don’t agree with the policies of Labour, full stop, or everything that comes out of their mouth. It’s a ridiculous association.”

The counter-argument is that, as a high-profile employee of Chelsea, Terry is representing his club, as well as working in an environment featuring different ethnic backgrounds. Indeed, Chelsea’s academy staff hosted an Iftar party just a week earlier for players and Muslim fans marking Ramadan. Another event was held at Stamford Bridge, involving 400 people, to celebrate Eid.

So, how does it make them feel that someone of Terry’s stature — a Chelsea icon, no less — would go down this route?

What Jordan failed to appreciate, perhaps, is that Terry is not just an ordinary ex-footballer with an ordinary story. There is important context. And that context is one of the reasons why, in Powar’s words, it “sets off some alarm bells”.

That history, in short, involved Terry shouting “f*****g black c**t” at Anton Ferdinand during a Premier League game against Queens Park Rangers in October 2011, sparking the chain of events that led to him being charged with a criminal offence and the England manager, Fabio Capello, resigning in protest at the Football Association’s decision to strip him of the captaincy.

John Terry’s confrontation with Anton Ferdinand in 2011 continues to hang over him (Glyn Kirk/AFP via Getty Images)

Terry’s defence when the case went to trial was that he actually said — note the question mark — “f*****g black c**t?”. It was all about that question mark. Terry’s argument was that in the noise and commotion of a big match, he thought he had heard Ferdinand accusing him of using those three words and responded, as his legal team put it, with “sarcastic exclamation”.

The prosecution could not disprove that version of events and Terry was acquitted. He was, however, banned for four matches and fined £220,000 ($350,000 in 2011) by an FA disciplinary panel that found his defence to be “improbable, implausible and contrived”. In other words, he was not just found to have said the offending words, but also to have lied to cover it up.

Terry has always maintained that he is not, in any way, racist. Yet Chelsea took their own disciplinary action, including a substantial fine, and nobody should think they are ignoring the latest issue, either. The club’s procedures mean that any employee in this position — even one of the greatest players in their history — would be challenged about it via official channels internally.

Powar is also uneasy. “He is now is in a position of responsibility in football,” he says. “It does raise concerns about his suitability for that role (at Chelsea), particularly given his previous history.”

So what should the club do?

“Any organisation with standards should be calling that individual in, addressing it directly, and making it clear that representing the club comes with responsibility,” says one former Chelsea player, who we will call Player A. “In most industries, this would lead to serious consequences. Football shouldn’t be treated differently.”

Player A has to remain anonymous because of a high court order as part of a legal action that he, and other ex-players, took against Chelsea because of the culture of racism they had to endure from coaches Gwyn Williams and Graham Rix in the 1990s and early 2000s. The former players won their case in 2022, leading to a public apology and damages being paid.

“When someone in a position of influence at Chelsea, in particular John Terry, behaves in a way that causes legitimate concern among communities, the response should be immediate and decisive,” says Player A.

“This isn’t just about public perception, it’s about duty of care. Chelsea have players in their academy and first-team environment from diverse backgrounds, including Muslim players. If you are a young player seeing that kind of public behaviour, you will naturally question how you are viewed and whether the environment is truly safe for you.”

That leaves Chelsea in a highly uncomfortable position, bearing in mind one of their equality objectives is “ensuring we are drawing from all parts of society and that our colleagues reflect the diverse environment that surrounds the club”.

Chelsea have made considerable efforts to get away from their past, when they were beset by long-standing problems with racism. As such, the strong likelihood is that Terry will be required to explain his stance and then the club would decide what, if anything, needs to be done.

“Technically, it could be a trigger for a safeguarding inquiry,” says Powar. “You would have a formal inquiry, you would question the individual and, if he is working with young people and ‘liking’ these kinds of posts, somebody should be saying, ‘Hang on a minute, what’s behind this? Talk to us about your approach to young people and (working with) people from a different background’. Because these are people, under Rupert Lowe’s proposals, who would be deported.”

What Terry may also have to understand is that, if he still harbours ambitions of going into management, these are the kind of reputational issues that any future employer would have to weigh up.

It was reported in a 2020 television documentary, Anton Ferdinand: Football Racism and Me, that Terry had declined to take part. He dislikes seeing this part of his life raked up. Surely, though, he must understand it will keep happening if he is applauding Instagram posts (or clicking a love heart to represent a ‘like’) that are, by their very nature, divisive.

Kick It Out has received complaints and the English Football Association may also get involved. Recently, the FA wrote to Sir Jim Ratcliffe, co-owner of Manchester United, over his claims that the UK had been “colonised by immigrants”.

“Many participants in football, from club owners to players, carry a weight of responsibility, especially if they are in a position of seniority or have a strong bond with a fanbase,” says Sanjay Bhandari, chairman of Kick It Out, addressing the Terry issue.

“Their influence can extend far and wide, so they must be mindful of their language or endorsement of views that can impact minority communities. This goes beyond the academy player, whose family comes from an immigrant background or whose sister or mother might wear a burqa. It can impact fans from west London or across the world and, importantly, it can also be used to validate the views of others who may seek to cause division or harm.

“At a time when society has become more polarised, football and its participants have the power and responsibility to make all communities feel welcome.”

Several sources present Terry as someone who has accepted his current position in football and is enjoying his life. He is fabulously wealthy and making the most of his opportunities to see the world and pick and choose what is on his schedule. Remember, too, that this is the man who was described in court by Bruce Buck, then Chelsea’s chairman, as having “almost uncanny mental strength”.

Few players in the English game can match John Terry’s CV (Rob Newell – CameraSport via Getty Images)

Yet that is not the same as saying that he has entirely given up on his plan to be a Premier League manager. Hypothetical, perhaps, but imagine the questions Terry would encounter at press conferences if he took a job in the coming weeks or months. He would almost certainly be grilled about this recent controversy, and so would the people above him. Can potential employers be blamed if they wonder whether it is worth the hassle?

As it is, Terry has admitted he was “frustrated” to be overlooked by Chelsea for the stand-in manager’s role before Liam Rosenior replaced Enzo Maresca as head coach in January. Calum McFarlane, the under-21s coach, took the role instead for games against Manchester City and Fulham, despite his modest playing career.

Asked if he was annoyed by the decision, Terry told the Golf Life YouTube channel: “Not annoyed, probably more frustrated, because I was certainly part of that under‑21s group (previously). Calum took the first team, did really well and got a result (1-1 at Manchester City). I should have been part of that.

“People have to make decisions. Clearly, the owners or whoever made those decisions — the sporting directors — have gone, ‘No’, not to include me… I don’t know why.”

Chelsea’s reasoning was largely based on the fact that McFarlane, unlike Terry, was a full-time member of staff. He was already on the scene, in other words, and so well regarded that he was subsequently promoted to Rosenior’s first-team staff.

Terry, meanwhile, remains on the edges. He prefers to eat lunch in the first-team building, rather than the academy, and was invited into one meeting by Rosenior after they were introduced on the training ground. Terry sat at the back of the room while Rosenior gave the players his instructions.

Otherwise, Terry will often be at the Kingsmeadow stadium for Chelsea’s under-21 games, watching from the stands and occasionally offering little pointers to the coaches and players.

John Terry watches a UEFA Youth League tie between Chelsea and Barcelona in November (Warren Little/Getty Images)

On other occasions, he has provided the stardust when Chelsea have been making a pitch to potential academy recruits. Terry would accompany Jim Fraser, then Chelsea’s head of youth development, to meet the boys and sometimes have dinner with the families. Even if the players were too young to know who he was, their parents usually did.

More recently, Terry visited Bangkok on behalf of Chelsea for a sponsors’ event and received the kind of reception that would have reminded him of his immense popularity among the club’s supporters worldwide. He remains a hero to many.

For now, however, Terry’s priorities appear to be split between Chelsea and his numerous other events, for work and pleasure, in a busy diary. He and his wife, Toni, have a mansion in one of the leafy villages near Chelsea’s training ground. The couple, parents to twins Georgie and Summer, have made huge profits from buying, renovating and then selling other properties, including one bought by the Omani royal family for £16million.

These days, the man who inspired a ‘Captain, Leader, Legend’ banner at Stamford Bridge could also be described as a philanthropist. His charity, the John Terry Foundation, is one example of why his friends and allies say there should be more focus on this side of his life (though nobody from Terry’s camp, including Terry himself, wanted to be interviewed for this article).

Terry intervened personally when he saw a feature on BBC Breakfast about the Amputee Lionesses. It is a wonderful story, how he invited them into the training ground and provided a private box for them to watch Chelsea Women take on Real Madrid in the Champions League. His foundation has provided grants for all sorts of good causes, including several children’s charities, and Terry ran the London Marathon last year with ex-Chelsea team-mate Jody Morris to raise another £52,000. These are the stories that show him in his best light.

Perhaps, though, it will always be complicated when it comes to John George Terry and trying to unpeel the layers that make him such a polarising figure.

While Rosenior tries to win over a sceptical Chelsea fanbase, Terry now has a background role in which he posts videos on TikTok to offer his tactical thoughts before and after matches. He appears on various podcasts and has embraced social media. Yet he is seldom on television or the big football shows. Some of the regular pundits and broadcasters, speaking anonymously, believe he would be an awkward pick.

In the first two seasons of Baller League, he had a managerial gig with a six-a-side team called The 26ers — a nod to his shirt number at Chelsea — as part of what the organisers have called a “new era for football”, shown live on Sky Sports and led by a mix of YouTubers, ex-players and TV personalities.

“I was surprised,” says Player A. “Baller League involves players, creators, and influencers from diverse backgrounds, including Muslim participants. When you bring in someone who is already a controversial figure, you have to consider how that makes those individuals feel and whether it contradicts the culture you are trying to build.”

A spokesman for Baller League told The Athletic: “John Terry managed during seasons one and two, but is no longer involved.”