Levy's image has been synonymous with Tottenham for the past 24 years. Photo: SS

Levy's image has been synonymous with Tottenham for the past 24 years. Photo: SS

In his final interview with Gary Neville on Sky Sports' The Overlap, Levy stated, "When I am not here, I am sure I will be recognized." This statement seems almost prophetic. Just one month later, he departed, leaving a significant question: will he receive the recognition he believes he deserves, or will his legacy be forever overshadowed by Tottenham's repeated near misses on the field?

A shrewd businessman

Levy has proven himself a masterful financial operator, transforming Tottenham into a true economic powerhouse in football. He was the driving force behind the world-class infrastructure the London club now possesses, from the magnificent 1.35 billion USD stadium—comparable to any venue in sports—to the state-of-the-art training center at Hotspur Way in Enfield.

Beyond that, Levy skillfully diversified the club's operations. He transformed the stadium into a multi-purpose entertainment center hosting NFL games, rugby matches, boxing events, monster truck races, and major concerts. This not only significantly increased Tottenham's revenue to 711.87 million USD last year but also positioned the club as a financial force in the modern football industry.

Outside of pure football, Levy could be considered one of the best executives in Premier League history, keeping costs low while maximizing revenue. Football finance expert Kieran Maguire described Tottenham as "the most profitable club in Premier League history" thanks to revenue from the new stadium, a low wage structure with a wage-to-revenue ratio of only 42%—the lowest in the league—and a cautious approach to transfer spending.

Tottenham Hotspur Stadium is a major landmark of the club in the Levy era. Photo: Tottenham Hotspur FC

Tottenham Hotspur Stadium is a major landmark of the club in the Levy era. Photo: Tottenham Hotspur FC

Tottenham made a profit in 13 of the 15 seasons before moving stadiums. While the current debt of 1.145 billion USD is substantial, it primarily stems from building the new stadium, a dream for many other clubs. Moreover, amid London's scarce and expensive land, Levy managed to build the new stadium on the site of White Hart Lane, keeping the club in its historic traditional area. Levy even dared to involve Tottenham in the previous Super League negotiations, despite the team not having won a domestic title since 1961. Under Levy, Tottenham's value skyrocketed from 107.8 million USD when he took over in 2001 to 3.5 billion USD, according to Forbes in early 2025.

Former Tottenham manager David Pleat said on BBC Radio Five Live: "To achieve success in modern football without vast sums of money is very difficult, and what Tottenham have done in the last two decades is astonishing. A magnificent stadium, a top-notch training center in Europe, and the club is in a good position with careful management. Levy is no more stringent than any other chairman; he simply seeks to protect the club and take care of its finances. As a club manager, I don't think anyone is sharper than him. I think he has taken very good care of Tottenham."

Overly cautious transfers

Levy's meticulous and cautious negotiating style, always determined to secure the best transfer deals, became his trademark. However, it also became a source of constant criticism throughout his tenure. His reputation as a tough businessman was solidified by former Man Utd manager Alex Ferguson, who once described negotiating with Levy as "more painful than a hip replacement."

This was evident in the transfer of Harry Kane, who scored 280 goals in 435 appearances for Tottenham. The English striker believed a "gentleman's agreement" with Levy would allow him to leave in 2021 if the team didn't finish in the Premier League's top 4. Levy dismissed this belief, forcing Kane to stay. Eventually, Tottenham sold him to Bayern for 116 million USD plus add-ons in August 2023—a deal Levy considered financially sound.

Harry Kane during a training session at Bayern's Saebener Strasse headquarters in Munich on 2/1/2024. Photo: Reuters

Harry Kane during a training session at Bayern's Saebener Strasse headquarters in Munich on 2/1/2024. Photo: Reuters

However, there were times when Levy's caution led to missed opportunities. "Typical Levy" is a common refrain among Tottenham fans lamenting his hesitation in crucial transfers. Recently, he allowed Arsenal to snatch English forward Eberechi Eze in a dramatic transfer. Tottenham had been in lengthy negotiations with Crystal Palace, but they allowed their North London rivals to swoop in and seal an 81 million USD deal just hours after Levy and his team finalized the details.

Previously, the 115 million USD windfall from Gareth Bale's sale to Real Madrid was not effectively reinvested. In the summer of 2018, after consecutive top-three Premier League finishes under Mauricio Pochettino, they didn't sign a single first-team player, coinciding with the new stadium's construction.

Critics argue that Levy's determination to run Tottenham on a sound financial footing lacked ambition, especially compared to consistently successful clubs. While Tottenham's transfer spending has only been surpassed by three other Premier League clubs in the past 9 years, a sense of stagnation persists, leading to on-field consequences.

On-field failures

Levy's reign has been overshadowed by Tottenham's lack of on-field success, despite regularly competing in European cups and consistently finishing in the top half of the Premier League. Giorgio Chiellini once described Tottenham as "always lacking something in decisive moments." Antonio Conte, a former Tottenham manager under Levy, famously exclaimed, "20 years with the same owner and they have never won anything. Why? The fault is with the club, or with every manager who has worked here?"

In the past 24 years, Tottenham has won only two trophies: the League Cup under Juande Ramos in 2008 and the Europa League last season. Levy faced criticism for sacking manager Ange Postecoglou just 16 days after winning the Europa League final against Man Utd, securing their first trophy in 17 years. A recent Sky Sports survey showed that 69% of Tottenham fans considered Postecoglou's dismissal a mistake.

Levy will forever be associated with the instability surrounding Tottenham, including 12 sacked managers during a period that saw the team reach 16 semi-finals and 7 finals, excluding the recent European Super Cup. Thomas Frank became the 14th permanent manager under Levy when he succeeded Postecoglou.

Winning the 2025 Europa League was a rare sporting achievement in Levy's nearly 25 years running Tottenham. Photo: AP

Winning the 2025 Europa League was a rare sporting achievement in Levy's nearly 25 years running Tottenham. Photo: AP

In his pursuit of success, Levy attracted renowned Premier League winners like Jose Mourinho—who was controversially sacked just days before the 2021 League Cup final against Man City—and Conte. There were also failures, like Nuno Espirito Santo, sacked in November 2021 after just 4 months in charge.

Before the 2025 Europa League triumph, Tottenham came closest to major silverware in 2019, reaching the Champions League final, where they lost 2-0 to Liverpool in Madrid. The aftermath saw the popular Mauricio Pochettino lose the support he believed he deserved from the board, leading to a rift with Levy and his dismissal 6 months later.

Pochettino's era best reflects fan frustration: Tottenham finished third, then second, then third in the Premier League; played two consecutive FA Cup semi-finals; and reached a Champions League final. Amidst this run was a quiet summer transfer window, leading to a poor start in their new stadium, and Pochettino’s departure.

Levy's Tottenham presented a paradox: before each match, the stadium played a historical video with a rousing soundtrack and Danny Blanchflower's words, "football is about glory." Yet, the team on the pitch represented a club prioritizing finances over achievement.

Fan discontent peaked with regular protests outside the stadium, featuring banners like "Our game is about glory, Levy's game is about greed," or "24 years, 16 managers, 1 trophy - time for change."

Decisions like increasing season ticket prices to among the highest in the Premier League, removing senior ticket concessions despite opposition, and using the government's furlough scheme during the Covid-19 pandemic fueled further controversy. All this occurred while Tottenham posted record profits and Levy was the highest-paid executive chairman in the league.

Behind the scenes and the post-Levy era

Levy's tough reputation masked a rarely seen softer side. Those close to him insist he was "hurt" by the fan protests. Levy rejected the notion that he only cared about Tottenham's off-field success and claimed the team's failures hurt him as much as any fan. "Their pain is my pain," Levy told Gary Neville on The Overlap when asked about the boos and discontent he faced last season, when the team dropped to 17th in the Premier League.

Tottenham fans protest against Levy before the match against Man Utd in February 2025 outside Tottenham Hotspur Stadium.

Levy is described as "shy, quiet, and hardworking," not the cold figure perceived by the public. Sources close to Levy revealed to The Athletic that some of his management issues stemmed from "not being surrounded by the best people." His reluctance to engage with the media often led to unclear messaging.

News of Levy's resignation may have been shocking, but in hindsight, there were signs. In February 2025, when Tottenham fans demanded his resignation, Levy stated that "all options are being considered." Just last month, in his interview with Neville, he hinted at contemplating his legacy. At 63, Levy missing the European Super Cup to help his daughter settle into university life in America could signal a shift in priorities.

Changes in Tottenham's leadership structure began late last season. Vinai Venkatesham, former Arsenal CEO, was appointed Tottenham's new CEO in April. Peter Charrington, a director of ENIC Group—the club's owner with an 86.91% stake—joined the club's board in March as a non-executive director. Levy retains a minority stake but is no longer involved in day-to-day operations.

Venkatesham (right) will replace Levy in running Tottenham in the near future.

A source close to the Lewis family, owners of ENIC, told The Athletic that the move aimed to deliver what fans wanted: "More wins, more regularly." Levy's critics hope the club will be more ambitious under Venkatesham and Charrington, adopting a more aggressive approach like Arsenal recently.

However, some wanted Levy to change, not a complete leadership overhaul. If the Lewis family is preparing to sell Tottenham, funding from America or the Gulf is possible, but it comes with risks like "sportswashing" or the Glazer model, unpopular at Man Utd, compared to the Fenway Sports Group's success at Liverpool.

Will Tottenham's future glories—if they do come—grant Levy belated recognition from the club's fans? Or will they have further reason to believe he should have delivered more nights like the Europa League triumph?

While the future remains uncertain, Levy's departure marks a new beginning for Tottenham. It brings optimism to fans who tasted historic success in May but grew weary of repetitive cycles and outdated approaches.

Perceptions of Levy, whether positive or negative, are likely solidified in the minds of most Tottenham fans. But over time, the question of his legacy remains open. Only time will tell.

Compiled by Hoang Thong