In December 2000, Tottenham Hotspur announced the exit of Alan Sugar as chairman and began a new era in which Daniel Levy assumed the reins.
Sugar, who later became Lord Sugar, will be most familiar to younger readers as the growling star of the British edition of The Apprentice. When he stepped down a few days before Christmas in 2000, the landscape of English football was radically different to the sport we see today. The domestic television deal yielded £167.5million per season to be shared across 20 clubs. Twenty-five years later, it is £1.675billion ($2.26bn) per season — and that’s before we get onto the international rights.
At Tottenham in 2000, the record transfer fee was £11m to sign Sergei Rebrov from Dynamo Kyiv. The British transfer record was Nicolas Anelka’s £22.5m move to Real Madrid from Arsenal. This summer, Tottenham signed two players — Mohammed Kudus and Xavi Simons — each for over £50m, yet Tottenham’s summer spend was only the seventh-highest in the Premier League, such is the startling largesse of England’s top flight.
It has been a period of monstrous growth. When Sugar sold his stake in Tottenham, the deal gave Spurs a valuation of £60 million. The Tottenham of 2025 would sell, most likely, for between two and three billion.
In the Premier League soap opera, Levy has been a central and recurring character, central to so many plot lines. He has hired and fired some of the most famous coaches in world football, including Jose Mourinho, Antonio Conte and Mauricio Pochettino. He negotiated a then-world-record sale of Gareth Bale to Real Madrid for £85.3 million ($100 million at the time). He was one of those executives of leading Premier League clubs who plotted to tear the sport upside-down, jumping into the European Super League in 2021 before pulling out within 48 hours. He is emblematic of a set of executives who became lightning rods for supporters; figures of fascination and frustration during transfer windows, targets of anger when season ticket prices rise, and rarely at the disposal of media or supporters for questioning.
In the vacuum that Levy’s hush created, a cartoonish picture emerged, drawn from anecdotes that have been drip-fed over decades. Sir Alex Ferguson described him as “more difficult to deal with than a hip replacement” when it came to transfer negotiations, such was the former Manchester United manager’s frustration when signing Dimitar Berbatov from Tottenham in 2008. Manchester City manager Pep Guardiola sarcastically called Levy “the big master of negotiations” when Spurs refused to sell Harry Kane in 2021.
Levy certainly drove a hard bargain and wished to run his club sustainably; Spurs were the most profitable current Premier League club during his 25 years at the helm as revenues increased more than tenfold. Those figures will simultaneously impress and infuriate; on the one hand, the finances were always protected, yet on the other, what might have been possible if the headroom afforded a little more risk in the transfer market and a little more generosity with ticket pricing?
Yet the tough exterior also had a more gentle side, such as the time he called Harry Redknapp on the night he had sacked his manager, to ask if they could still be friends. The way Levy saw it, managers in the Premier League are handsomely paid — whether they succeed or not — and it should not be taken personally if clubs opt for different ways forward. Levy’s wife, Tracy, used to joke that he and Pochettino spoke so often she wondered if the Argentine was the third person in their marriage, while on one vacation in Patagonia, Argentina, the pair went rafting together on the rapids — where Pochettino at one point needed to rescue Levy from the water.
Levy’s status in English football was raised when transfer windows, and particularly deadline days, transformed into dramatized events for television, before then being turbocharged by social media. Levy’s eye for a deal, and willingness to take business down to the wire, made him one of the most famous and talked-about executives in English football.
And for all the scandal the Super League entailed, it also revealed how Levy had thrust Tottenham into the most powerful rooms of English and European football.
Tottenham have come to be known as one of the “Big Six” clubs in the Premier League but they did not actually finish in the top six until the fourteenth season of the Premier League in the 2005-2006 campaign, and they have won only three trophies — two League Cups and one Europa League — since the inception of the Premier League in 1992.
Their trophy haul and league placings pale in comparison to those of Manchester United, Manchester City, Chelsea, Arsenal and Liverpool, who make up the remainder of the Big Six.
Tottenham’s league positions improved considerably from 2010 onwards, finishing outside the top six on only three occasions in the past fifteen years — albeit in the top two only once — and reaching the Champions League final in 2019. Tottenham’s improved on-field performance provided Levy with the platform to push his side’s case even harder in Premier League boardrooms.
Consider, for example, a meeting between owners and executives from the other Big Six clubs at London’s Dorchester Hotel in 2016, where the clubs were discussing an expansion of the International Champions Cup — a pre-season friendly tournament — into an idea that may well have resembled something much like the eventual Super League. According to those familiar with the discussions, who asked to remain anonymous to protect relationships, Levy’s concern, when he found out about the meeting, was not about the content of the plans at that stage but in fact a deep frustration that Tottenham had not been included.
Not long after, Tottenham were very much back in the club at a Premier League shareholders meeting in November 2016. Premier League clubs were considering a series of offers from Chinese broadcasters for Premier League broadcast rights. While the league’s chairman Richard Scudamore asked for an immediate decision, the Big Six executives, this time including Levy, decided to take charge, scurrying away into a huddle in the corner of the room before coming back with their joint consensus. Increasingly, the six started to act as a group of their own, under the belief that because their coaches and players command the eyeballs, they should be entitled to a larger share of the revenue.
That Big Six, however, is not always a unified force. Levy worked hard to make his own club sustainable, which is why he feels so passionately that cost controls should be implemented on those rivals with access to state-backed resources. Tottenham joined Arsenal, Liverpool and Manchester United in 2013 — on Arsenal letter-headed paper — asking the Premier League to “curb the inflationary spending which is putting so much pressure on clubs.” The target was Manchester City. Tottenham were then part of a group of nine clubs, also including Burnley, Leicester, Newcastle United (pre-Saudi takeover) and Wolves, who went so far as to write to the Court of Arbitration for Sport to try and ensure that a two-year UEFA ban against Manchester City playing in the Champions League was upheld — a ploy which did not succeed. Levy has been supportive of attempts by the Premier League to introduce stricter rules to limit related-party transactions and avoid scenarios where businesses linked to owners of Premier League clubs might be able to inject cash into teams via backdoor sponsorships.
For all Tottenham’s growth, they do remain the smallest of the six on a global scale. This is exemplified by being the only one of the six with fewer than 10 million Twitter followers. Tottenham are tens of millions of followers behind the other five on Instagram. If Tottenham are not quite seen as equals, Levy was certainly considered worthy of being in their conversation.
As much as he may have exasperated just about every club in the Premier League over one transfer or another, he also commanded huge respect when he spoke up in shareholder meetings. Clubs such as United, Arsenal and Liverpool viewed him as someone to be cultivated, rather than alienated, particularly when votes around the table required 14 in favour to succeed.
Owners such as the Glazer family, the Kroenkes and Fenway Sports Group admired Levy’s preparedness to push boundaries. Tottenham were one of those teams who signed up for an Amazon Prime documentary, ideally timed while Mourinho was at the club. Crucially, Levy earned respect from rival owners, particularly the Americans at Liverpool, United and Arsenal, by building a state-of-the-art stadium, which produces close to £5m per game. It seats 62,850 people and it is as close as you can get to a cash machine in modern football; monetised through major concerts (Beyonce most notably), go-karting and a partnership with the NFL that sees Tottenham’s stadium host a minimum of two NFL games per season.
Levy does not leave behind a trail of glory but he will always be the man who took Tottenham into the future; traversing the bedlam of the Premier League as the league’s longest-serving chairman. The stadium stands as a physical monument of his efforts, a shrine to his reign. Now, fans will hope it serves as the rocket fuel to catapult Spurs into a new era.
(Top photo: Tom Jenkins/Getty Images)