From early on, it was established that the Portuguese manager would be “a pain in the ass” for the young midfielder. He would make him train hard, push him to the limit and unleash the potential that hadn’t quite been fulfilled.
There have been glimpses of that in patches since Mourinho’s arrival. But Alli remains a frustrating figure at Spurs. So much was expected of the England international after those first two seasons for the club following his arrival from MK Dons.
Perhaps he has reached his ceiling. Or perhaps there is a way of getting the very best out of him. Whatever the case, there seems to be something missing.
The first game of the new season was disappointing for everyone associated with Spurs but especially Alli, who was withdrawn at half-time and replaced by Moussa Sissoko.
He looked a forlorn figure on the pitch for the 45 minutes he played, nullified by an organised Everton team and unable to have any real impact on the game. Mourinho’s comments after the 1-0 defeat seemed telling.
“We were lazy in our pressing,” he said. “That is a consequence of bad fitness, bad pre-season. Our pressure up front was very, very poor. When you have lazy pressure, you let opponents build from the back.”
Alli was then left out of the squad entirely for the second game of the season – a 5-2 win over Southampton on Sunday.
It is not the first time Mourinho has been heard using the word lazy in recent weeks. In All or Nothing , he calls Alli “lazy”, albeit slightly tongue in cheek, and singles him out as a bad trainer.
And, of course, there was the face-to-face conversation between the two, one of the biggest talking points from the documentary.
“I have no doubts about your potential,” Mourinho told the player. “I saw you do incredible things in incredible matches. But I always felt that you had ups and downs.
“There is a huge difference between a player who has consistency and a player who has moments. That is what makes the difference between a top, top player and a player with top potential.
“I don’t know if it is to do with your lifestyle – if in one period you were an amazing professional but in another period you felt you had become a party boy. I have no idea – only you can know that. I am 56 now and yesterday I was 20. Time flies. One day I think you will regret it if you don’t reach what you can reach.”
What is immediately obvious is that Mourinho wants Alli to succeed. He is aware of his ability and doesn’t want it to be squandered. Generally, though, he is a manager who doesn’t give second chances, someone who has no qualms about dropping players unable to meet his demands.
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The new season has barely got started, but already the signs are concerning for Alli. He is 24 now, no longer the new kid on the block, no longer the fresh-faced youngster unburdened by the weight of expectation. He is an established international, a player who many thought would, by this point, be truly world-class.
But consistency is lacking, and Mourinho has never been known for his patience. This season feels like a hugely significant one for Alli. He is young enough to get fully back on track and continue on the upward trajectory of his first few years at Tottenham.
But time, as Mourinho so shrewdly observed, passes quickly. Before he knows it, Alli will be in his late 20s. How he looks back on the best years of his career will depend very much on what he does to get out of this lull.