It was just under two months since the 2019 Champions League final. Tottenham Hotspur had lost 2-0 to Liverpool that night in Madrid, but the miracle work from Mauricio Pochettino & Co. was crafted long before.
Spurs had not signed a player all season long and had to contend with Harry Kane missing months due to injury. With the help of Lucas Moura, Heung-min Son and Fernando Llorente amongst others, they reached their first European final since 1984 and finished fourth in the Premier League.
A month later came a first statement signing in years as Tanguy Ndombele smashed the club's transfer record with his £60 million move. The Frenchman was a player Pochettino had wanted to revitalise a midfield that had lost Mousa Dembele and Victor Wanyama.
It appeared as though, following years of Pochettino coaching shrewd purchases into Premier League talent, the Tottenham board were finally ready to deliver the investment he had been crying out for.
Still, another month went by and that significant rebuild left Pochettino wanting. Teenager Jack Clarke had been signed, and later Ryan Sessegnon and Giovani Lo Celso. This quartet was not enough for a radical revamp and, ultimately in their individual cases, largely unsuccessful.
Just a few weeks before the 2019/20 season got underway, then manager Pochettino admitted to not being involved in transfer dealings.
"I am only coaching … trying to get the best from [the current players]," he said in an Audi Cup press conference.
"Sell, buy players, sign contract, not sign contract - I think it is not in my hands, it's in the club's hands and Daniel Levy.
"The club needs to change my title and description. Of course I am the boss deciding the strategic play, but in another area, I don't know. Today, I feel like I am the coach."
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Later, in October, executive chairman Levy would seemingly shift the blame back on the Argentine, stating in a meeting with the club's Supporters Trust that Pochettino "didn't want to sign someone for the sake of it. He felt there were sufficient players in the squad, and that those coming back from injury would be like new signings."
Levy demonstrated less than four weeks later where the true power was at Spurs, and it was not in the dugout. Pochettino was sacked, replaced by Jose Mourinho - one of Levy's dream appointments - for reportedly almost double the salary.
For 25 years of the Levy era, managers came and went, transfer strategy was hit and miss but throughout it was clear that he had significant control on and off the pitch, with Pochettino, the club's most successful manager of the Premier League period, struggling to assert his authority after five years at the helm.
Except now, just shy of seven years later, not only is Pochettino long gone but Levy also. Someone who appeared nigh untouchable during his time in north London, the 64-year-old was ousted as ENIC Group and the family of owner Joe Lewis took control to move Spurs into a more modern way of running things.
It is 2026 and Roberto De Zerbi is less than four months into his job at Tottenham and already looks to have had more say in transfer business than Pochettino ever did.
De Zerbi's spending spree
It is only July and already Tottenham Hotspur are in the midst of a transfer window unlike any in recent times. £237 million spent makes it Spurs' second highest transfer expenditure in their history.
But unlike the 2023/24 season where the £275 million was spread across nine players, and counterbalanced with the big money sale of Kane and offloading the wages of Hugo Lloris, Davinson Sanchez and Harry Winks, this current window's total has been accumulated from just three signings - Jan Paul van Hecke, Matheus Fernandes and Sandro Tonali.
With the latter two, the Lilywhites broke their transfer record twice within the space of a week, and the Italy international became the first time the club will pay £100 million for a player. Add to that some smart free acquisitions in Andrew Robertson, Marcos Senesi and Martin Dubravka.
Ball playing defenders and low-lying midfielders adept at progressing the ball - these are De Zerbi signings. Unlike Pochettino's big window the summer before he was sacked, all of these players have Premier League experience. And most are in or nearing their prime ages or provide valuable leadership credentials.
And, to reiterate, it is only July. Spurs are not famous for doing this kind of business this early.
Moreover, this shift is also coming to sales, with Football London reporting that Tottenham have 'made it clear that there will be a new policy with exits at the club' where 'players [are] sold for better value and at the right time.'
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Circumstances between De Zerbi and Pochettino differ, of course. The Italian was a highly-rated free agent who was given the unenviable task of keeping Tottenham in the Premier League when form and momentum pointed towards the Championship.
Risks were made on De Zerbi's end in choosing to join: What if it did not work out? What would happen to his reputation? Would it scupper his chances of getting another top job?
As West Ham United dwindled and the Lilywhites did just enough and little more to stay in the league, Tottenham then had to cough up their concessions.
The primary one being allowing De Zerbi more of a say over recruitment to create a team in his image. In turn, Tottenham have crossed an expenditure Rubicon that many believed they would never dare tread near.
Power to the person
Watching on from across the Atlantic, sporting in his enlightened university tutor look, Pochettino could rightfully feel aggrieved, having led the team of coaches that turned Spurs into a regular Champions League outfit and to that final at Wanda Metropolitano.
The Argentine has always been magnanimous about the Lilywhites and Levy himself since being shown the door, but his frustrations were there to witness at the time.
"I am not open to start a new chapter with no plan," he said in that same Audi Cup room, seemingly vocalising what he had been fighting against since joining in 2014. "With no clear idea, with not being transparent."
It was evident in the years after Pochettino left that Tottenham fell short in all three.
It is often seen a rarity in the modern game to give such power to managers, with Arsene Wenger and Sir Alex Ferguson the recurring examples of the old order of bosses who had their fingers in every facet of their respective clubs.
But look at the elite level of English football and you will see that this ilk of figurehead is more common than expected.
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Pep Guardiola and Jurgen Klopp are the clearest instances of this, moulding Manchester City and Liverpool around their tactical identities and personalities.
Mikel Arteta is the only boss in the Premier League with the title of manager, given to him by ex-Arsenal and current Tottenham CEO Vinai Venkatesham because the Spaniard was 'doing much more than being our head coach.'
Then, there is Unai Emery, who has been referred to as 'kingmaker' at Aston Villa for the power he wields.
Of course, clubs like Chelsea and Nottingham Forest showcase other structures based around their boardrooms, while famously Brentford and Brighton have been built around data and recruitment.
Under the ENIC ownership, Spurs have always been a myriad of these models but they have never quite provided a linear identity.
Pochettino's job title did change from head coach to manager to 2016, but that did not give him ultimate say in recruitment or vision for the club. As he said, they may as well have changed it back. Something they have never truly done is go all in on a manager.
Big club style
On The Overlap podcast, former head coach Ange Postecoglou claimed he was wanting to sign 'Premier League ready players' to help the team improve from their fifth placed finish in his debut campaign.
"I was looking at Pedro Neto, [Bryan] Mbeumo, [Antoine] Semenyo … Marc Guehi. I said if we're going to go from fifth to there [challenging for titles], that's what the other big clubs would do in that moment."
Both Pochettino and Postecoglou have admitted the club's situation in their respective tenures - constructing the new stadium, no European football - hampered the ability to spend, but De Zerbi's opening of the purse strings does cast a starker shadow on the lack of ambition afforded to them despite their success.
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Especially given Spurs were arguably one West Ham goal away - at Crystal Palace - from going down.
Even Antonio Conte could feel dissatisfied. Having brought Spurs back into the top four with his own mini miracle job in 2021/22, his parting words in the explosive press conference in Southampton show Tottenham were not keen to let the head coach near the reins of genuine authority.
"The fault is only for the club, or for every manager that stay here?," he said about Spurs' lack of consistent silverware.
"I have seen the managers that Tottenham had on the bench. You [Tottenham] risk to disrupt the figure of the manager and to protect the other situation in every moment."
Spurs would continue in this fashion into Postecoglou's spell. The Australian's 17th-placed league finish was reacted to in similar fashion to previous difficult moments - sacking the manager.
Even last season, when there was no Europa League to console them and a realistic chance of relegation, Thomas Frank to Igor Tudor showed that the change of face strategy was still not working. De Zerbi's appointment cajoled the club into embracing the more dictatorial method.
Managing power
Fat salaries can be enough to tempt many a man to even the most seismic of jobs. Football coaches, however, want ultimate control of their squad and thus the direction of the club as a whole, given both operate in tandem.
De Zerbi's previous job in England, down the A23 in Brighton & Hove, saw him ultimately lose the battle in trying to attain that control. He would eventually leave after two years because of disagreements with chairman Tony Bloom, with The Athletic reporting 'irreconcilable differences' in the pair's transfer hopes.
Bloom was keen to continue the analytics-based policy that had not only served the club so well but him personally, with his background in sports betting and poker. Meanwhile, De Zerbi was not content with milling about in midtable, urging bolder moves.
"He [De Zerbi] comes to me and says, 'Why are you talking about top 10, why don't you talk about top six?'," Brighton's chief executive Paul Barber recalled.
"It's the first time in my club career that I am almost encouraged by the head coach to push expectations publicly."
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De Zerbi himself would verify this in an interview with The Telegraph in 2025, echoing Pochettino's desires for having greater power over the team at large and recruitment.
"We reached a point where, after qualifying for the Europa League, I didn't understand what the next step forward was.
"And you can offer to double my salary, but if I can't see a dream or goal to achieve, I can't give my all as I would like.
"I would lose motivation and a purpose I always had in football."
Now, having dragged Spurs from the brink of catastrophe, De Zerbi has the perfect melting pot - a wealthy club that is totally in debt to him.
Upon beating Everton on the final day of 2025/26, his attention immediately turned towards cashing in the credit he had earned.
"My target now is finished, to stay up. My [next] target is to start pre-season with the team in my dream, in my head."
Time will tell whether Spurs' De Zerbi-centred future will work out. Of all the success Guardiola, Klopp, Arteta and Emery have had, there are still hazards. First, simply, is this the right person to go all in on, and then what comes after they are gone?
The latter question is particularly pertinent to Tottenham. Given backing a manager in this way is the last roll of the dice that the hierarchy have not yet landed on, the absence of any big picture planning may well be exposed again should the De Zerbi project turn sour.
Perhaps there is no going back from this, however. Questions that circled about the true financial might of Spurs in the transfer market have now been answered, and not investing in a similar, big money fashion will be harder to justify in future windows.
In other words, the die is cast.