Today, Spurs are one of the most profitable clubs in Europe, valued at over £2billion and boasting one of the best training centres in the country and surely the finest stadium in the world.
Levy has achieved all this without a penny of outside investment, making it an almost unparalleled feat.
Modest and unassuming, Levy would never describe himself as a visionary but that is how many who have worked with him see it.
“He always had an incredibly clear vision for the club,” says Brighton chief executive Paul Barber, a director at Spurs from 2005 to 2010.
“Right back to when I joined, he had that vision, which involved a world-class training ground and very significantly a world-class stadium.
“Not many football clubs have that kind of leader or patience or determination to deliver a project of that magnitude over a two-decade period.”
The £1.2bn stadium will surely go down as Levy’s greatest legacy and, post-pandemic, is expected to be another commercial game-changer.
With the infrastructure complete, Levy has told colleagues the ‘building blocks’ are finally in place to achieve the on-pitch success to match Tottenham’s off-field achievements.
The 2008 League Cup remains the only trophy of his tenure, so for all his achievements, Levy is still a divisive figure among supporters, with some believing he will always prioritise business considerations over sporting success.
Agree or disagree, I really liked to listen to him, spend time with him and learn from him ... Mauricio and Daniel still text each other.
Jesus Perez, assistant manager to Mauricio Pochettino
“We talked regularly about on-pitch success,” says Barber. “Despite some of the comments over the years that that hasn’t always been uppermost in his mind, it has.”
With Levy as ‘custodian’, as he describes his role, Spurs have ascended from mid-table mediocrity to Champions League regulars but his footballing vision has not always been as coherent as his business plan.
In the past two decades, Spurs have veered between different models, transfer strategies and styles of manager, going from Juande Ramos to Harry Redknapp, from Mauricio Pochettino to Jose Mourinho.
The eras of Redknapp and Pochettino, the two most successful of his nine managers, feel tinged by a sense of missed opportunity, particularly the Argentine’s five and a half years in charge.
“At some point, as everyone knows, visions were different,” says Jesus Perez, Pochettino’s assistant at Spurs and currently at Paris Saint-Germain.
“The circumstances of the club, they couldn’t please what the team needed or the manager needed to keep progressing. Because of the training centre and then the stadium.
“To keep that level and keep progressing and build a stadium, probably it was impossible.”
Among Levy’s big sliding-doors moments are the January 2012 transfer window, when Redknapp’s title-challenging squad was bolstered only by Louis Saha and Ryan Nelsen, and the unprecedented decision not to buy or sell any first-team players in the summer of 2018.
It was the beginning of the end for Pochettino, even if the team reached the Champions League Final in the following season.
“It was not because he didn’t want to sign,” says Perez. “It’s because the level that the team needed and the big decisions to allow players to go was really difficult.
“I saw on [one] deadline day how some deals went through and some didn’t. And no-one can explain it. I was at the club with Daniel and Becs [Rebecca Caplehorn, director of football operations] because Mauricio was in Barcelona.
“That’s why, agree or disagree, I really liked to listen to [Daniel], spend time with him and learn from him. We all did.”
Despite the sacking of Pochettino, who was replaced by Mourinho overnight in November 2019, Perez still warmly remembers the “thousands of hours” spent with Levy, sharing the contrasting challenges of their roles.
“Every day Daniel crossed to Mauricio’s office and he joined us on the topic we were discussing,” Perez says. “Then most of the time we had breakfast with him and lunch at the training ground. We, as a staff, never started lunch until Mauricio or Daniel was at the table. That’s something we always respected.
“Mauricio and Daniel still text each other and they have a very good relationship. We don’t have any bad feelings with Daniel. The other way around. It was a professional decision.
“At some point, we had to split but we will be back at Spurs for sure.”
Despite Levy’s reputation as an uncompromising businessman, warm relationships are a theme of his tenure and there are few clubs in the country who look after their own like Tottenham.
Shortly after becoming chairman, in 2002, Levy proposed an independent charity to care for former players, which became the Tottenham Tribute Trust.
“Daniel’s support has been unwavering,” says TTT chairman Jonathan Adelman. “The number of former players and staff TTT has been able to help over the years is quite a legacy and one I would hope Daniel can reflect on with pride.”
For Levy’s adversaries, it is occasionally a different story. Sir Alex Ferguson described dealing with Levy as “more painful than my hip replacement” after negotiations over Dimitar Berbatov’s 2008 transfer to Manchester United.
“It was a pure business deal and our relationship is good,” says Berbatov. “Whenever I go back we talk and joke about how things are now.
“He has built the club into a global brand. When I met him a few years ago, I told him I wish he’d built the stadium when I was there.”
Gareth Bale’s agent, Jonathan Barnett, sparred with Levy in summer 2013 over the Welshman’s world-record move to Real Madrid and thrashed out the deal to bring him back to the club on loan in October.
“I like dealing with him,” says Barnett. “I don’t find it painful at all, I actually enjoy it. He keeps his word. He’ll fight tooth and nail for his side but I find him very honourable. Once you agree something with him, he’ll stick with it, no matter what.
He keeps his word. He’ll fight tooth and nail for his side but I find him very honourable.
Gareth Bale’s agent, Jonathan Barnett
“It was all his idea to bring Gareth back. He convinced me and then I put it to Gareth.”
Those close to Levy insist the 59-year-old will keep working feverishly to elevate Spurs, with his work ethic and desire for improvement unceasing.
He has, for example, spent the shutdown ironing out snagging on the stadium, which was expected to take three years.
Levy will remain mindful of the value of Spurs’ assets, however, and ENIC seem unlikely to see out another two decades, with Hotspur Way already eight years old and the stadium likely to be surpassed by another club in the not-too-distant future.
In the short term, Levy has staked plenty on the decision to appoint Mourinho, which was driven by his remaining challenge: to ensure Spurs are as successful on the pitch and he has made them off it.