In most cases, the congratulations came begrudgingly. None more so than from Melwood given Liverpool had exerted plenty of effort in trying to pull off the same coup. A closing detail was for the teenager to meet his hero, Steven Gerrard, during a tour of the training complex, but the captain was sleeping as per his pattern a day prior to a game.
Bayern Munich, too, regularly had their scouts attending the youngster’s matches and they weren’t the only Bundesliga club drafting an extensive dossier on Dele.
Given the calibre of rivals ousted, Spurs chairman Daniel Levy revelled in the transfer win and happily digested the deal widely being labelled excellent business.
Privately, though, he wasn’t entirely sure if £5m was a smart outlay for a kid kicking about in League One.
Former Tottenham manager David Pleat was among several voices that convinced Levy to part with the initial fee, as it was a “no-brainer.”
There was not much room of negotiation over the asking price as Newcastle were trying to muscle in and the super clubs were still in play.
For everyone but the notoriously economic Levy, the figure was seen as small change.
Alli had already scored 12 goals in 25 league games that season when the announcement of the signing was made.
He was an England Under-19 international and was referred to as “the trump card” in the youth set-up.
Former Spurs technical director Franco Baldini believed Dele had the capacity to grow his valuation beyond Gareth Bale’s €100m mark.
And by the end of his second campaign with the North London club, that forecast was remarkably accurate.
Levy’s apprehension over the £5m fee naturally transformed into him regularly highlighting it as an example of Spurs’ shrewdness.
Under Mauricio Pochettino and in tandem with Harry Kane, Dele was decisive in positioning Tottenham as the dominant force in North London, repainting them as title contenders and Champions League regulars then finalists.
In the Amazon documentary of a similar name released in 2020, Levy has such a conversation with Tottenham manager Jose Mourinho.
Raising his hands skyward, the perplexed chairman says, “two years ago, he was here” referencing Dele’s status as a golden boy that was a star for club, an automatic pick for country and persistently linked with Real Madrid and Barcelona.
Mourinho further underlines that top billing, revealing: “Sir Alex Ferguson gave me only one advice in two-and-a-half years at Manchester United, buy Dele Alli.”
Now the reality is Dele can’t crack the Spurs squad, has made one league start this season, is on the fringes of Gareth Southgate’s thinking and is hoping for a loan escape to Paris Saint-Germain, where he can be reunited with Pochettino.
It would be easy, but unfair to pin the England international’s decline on Mourinho.
The truth is Dele’s diminishing powers predate the Portuguese’s arrival at Tottenham and most of the issues the manager has flagged – being “f****** lazy in training” and having the lifestyle of a “party boy” – were not new revelations.
If anything, Mourinho coaxed a brief revival resulting in four goals and three assists in seven games before it all went off the boil again.
There is a cocktail of contributing factors behind the fall, but it is worth pointing out that while he is only 24, this is Dele’s ninth year in professional football.
He has had to shoulder a lot of responsibility and expectation while navigating hype, celebrity, and scandal in front of a global audience.
It is a consistently taxing experience that allows for zero errors and feels far removed from the initial reasons for getting into the game itself.
A loss of joy
As a seven-year-old, Dele was already trying to muddle men in the tightest of spaces at Heelands Courts.
Even on the uneven surface and against physically opposing markers, he would scoop the ball over their heads or squeeze it through their legs with nutmegs becoming his trademark.
That bravery and audacity remained when he made his debut at 16.
Dan Micciche and Karl Robinson, who coached Dele at Dons, would spotlight his fearlessness and sheer delight at being on the pitch as two traits they hoped he’d never cede.
In an October 2018 interview with this writer, when criticism was already being channeled Alli’s way for his dwindling final third contributions, he insisted it was not affecting his affection for the game.
“Making it as a professional and reaching the Premier League is not an easy thing to achieve,” he said.
“It has taken a lot of effort to get here. I still enjoy the same elements of football I did as a kid and that’s very important,” he said.
“I never want to lose that happiness and excitement in my game, it’s a big part of the player I am.”
That seems to be exactly what has happened.
Three backroom staffers that have worked closely with Dele all independently flagged his visible lack of enthusiasm as a core reason for his current malaise.
“He’s just not Dele and hasn’t been for a while,” says one former Dons employee. “The spark, that edge that made him stand out and drove his game is gone.
“He was a street footballer that was better and looked like he was having more fun than everyone on the pitch, but since the World Cup in 2018, he has come across more and more strained.
“I think it’s too much football, too much too soon, too many bad influences, too much pressure, expectation and hate.
“I saw Jose in the documentary saying he needs to find what Dele’s motivation is and the thing is that was never ever a problem with him. He would walk on the pitch with a burning desire to be the very best. It’s quite sad because he is a shadow of the player I know.”
In an April 2016 column for The Telegraph, Gerrard – Dele’s footballing idol – foreshadowed this twist in the tale.
“Playing football is never more enjoyable or less stressful than when you first come to the fore,” he wrote.
“When you make an impact at an early age for club and country it feels like everything is going your way and the whole world is on your side. You wish this feeling could last your whole career.
“You pick up the paper and read a different article every day saying how fantastic you are.
Your club and international manager are asked to talk about your qualities every week so you can be presented as an emblem of a bright future. Ex-England players such as myself will write columns expressing their admiration and high hopes.
“You’re walking on air into the training ground, desperate for the next game, craving a chance to go up against the best.
“There will come a time when he finds it far more challenging; where he feels he is being singled-out for harsh treatment; where the carefree attitude of being a teenager with nothing to lose is replaced with a sense of responsibility he has to deliver every week; and where he feels he’s done well in a match, but not quite performed as spectacularly as many wanted, and is fending off criticism.”
Perhaps a change of scenery and working with the manager that coaxed the greatness out of him can be a tonic for Dele, but his loss of enjoyment for the game is only one part of the conundrum.
Tactical shifts, injuries and attitude
Thigh and hamstring problems stifled the player’s progress. But so have tactical shifts in recent years. When Pochettino switched between a 4-2-3-1 and a 3-4-3, Dele thrived combining with Harry Kane and Christian Eriksen from the left.
As the influence of Heung-Min Son grew, he was positioned centrally and was increasingly tasked with being a midfielder – in a three or a diamond – rather than an attacker.
More defensive duties and positional discipline did not suit his natural instincts and Mourinho recognised that too, commenting: “For me Dele is not a player to play positionally in midfield.
“He is a player to be playing close to Kane, following some dynamics that we train but a little bit of freedom to associate with attacking players. This I think is the best position for him.”
The challenge for Dele is the combo between Kane and Son has underpinned Spurs during Mourinho’s charge and their exacting standards in training is the example he expects the rest of the squad to follow.
As one Spurs source put, “the reason Dele is not playing is because of Dele.”
Problems away from the pitch
Dele has kept a fractured childhood unspoken, but tales of it have coloured tabloid spreads courtesy of revelations from his estranged parents, Denise and Kehinde.
At the age of 13, he moved in with best friend Harry Hickford and his parents, Alan and Sue, gaining the home stability he had long craved.
He disassociated from the Alli surname in August 2016 due to feeling “no connection” with it and understandably grew increasingly guarded as the better he did, the more personal betrayal he encountered.
As Pochettino once explained: “He is very sensitive, very intuitive and because he comes from a difficult background, you can understand that when you’re with him.”
And in Brave New World, a book that charts Tottenham’s 2016-17 campaign, Pochettino shares his concern over Dele’s inner turmoil.
“His WhatsApp photo of a cartoon of a boy surrounded by people who all want a piece of him suggests that he needs to be surrounded by the right people,” the former Spurs boss noted.
“I often think about that WhatsApp photo. John McDermott [Tottenham’s ex-academy chief] says that when the trough is full, the pigs come from all over to feed.
“The coach used to be the dominant voice, but now the player listens to so many others, especially those who promise the world.”
Various sources at Hotspur Way over the past two years have questioned some of the people Dele has in his circle. While he has issues with trust, there has been a feeling that a blind spot remains when it comes to some friends, which has contributed to the “party boy” branding.
Private videos in the possession of a small group have made their way to tabloids in the past and there has not been a shortage of daft behaviour on his part.
Mistakes are the norm for us all, but Dele has shared some of his faltering with the watching world.
More traumatic experiences have also been played out in the public sphere.
During lockdown, Dele was held at knifepoint by burglars in his home.
He suffered minor facial injuries after being punched before the thieves made off with valuables during quite a frightening ordeal.
Dele has had to manoeuvre through a mountain of personal hurdles mixed in with relentless professional expectations.
The young man Pep Guardiola called“one of the most fantastic footballers I have ever seen in my life” and who Pochettino described as “the most important player to emerge in English football in recent years” is now sadly on the periphery.
Surplus to requirements with the joy of the game sucked out of him.
Dele was meant to dominate and decorate fixtures between Tottenham and Liverpool. It’s a devastating turn that he is now just a sidenote to the main show.