It was only fitting that the end of Daniel Levy at Tottenham was as ungracious as those he had hired and fired in his time as CEO at Tottenham Hotspur.
Word reached The Boy Hotspur swiftly yesterday that the man many had learned to despise had not been sacked. In fact, he stepped down as Tottenham Hotspur’s executive chairman on September 4, 2025, after nearly 25 years in the role. However, reports indicate the decision was driven by the club’s majority shareholders, the Lewis family, suggesting it was not entirely voluntary.
The move followed a review by the Lewis family, who own Spurs through ENIC, aiming to prioritise sporting success after a mixed legacy under Levy.
Despite leading Tottenham to a world-class stadium and financial stability, fan frustration over limited on-pitch success—marked by only two trophies (the 2008 League Cup and 2024 Europa League)—and a 17th-place Premier League finish last season fuelled protests against him. Peter Charrington has taken over as non-executive chairman, with Vinai Venkatesham as CEO, signalling a new era for the club.
Hiring José Mourinho and Antonio Conte:
Levy admitted in 2023 that appointing trophy-proven managers like Mourinho (2019–2021) and Conte (2021–2023) was a mistake, as their defensive styles clashed with Tottenham’s attacking identity. Mourinho was sacked days before the 2021 Carabao Cup final, a decision widely criticised as poorly timed, while Conte’s tenure ended after public criticism of the club’s culture. These hires were seen as a misguided shift from the club’s roots.
Sacking Mauricio Pochettino and Ange Postecoglou:
Pochettino, who led Spurs to a Champions League final in 2019, was sacked five months later during a dip in form, a move many fans viewed as premature given his transformative impact. Similarly, Postecoglou’s dismissal in 2025, despite winning the Europa League (Spurs’ first trophy in 17 years), was seen as harsh and left a sour note, especially as it followed fan protests and a 17th-place league position.
Nuno Espírito Santo’s Brief Tenure:
Appointing Nuno in 2021 was a misstep, with his sacking after just four months due to uninspiring results and a lack of fit, highlighting Levy’s inconsistent managerial strategy.
Ineffective Spending:
Despite Tottenham being among the top spenders in the Premier League (over £500m on the first team since April 2019), Levy acknowledged transfer mistakes that had both financial and sporting impacts. High-profile signings like Tanguy Ndombele and others failed to deliver, with funds from Gareth Bale’s £85m transfer to Real Madrid in 2013 poorly reinvested.
Missed Opportunities:
In 2025, Tottenham were outmanoeuvred by Arsenal in the race to sign Eberechi Eze, a last-minute transfer blow that underscored Levy’s cautious approach in negotiations, often described as “penny-pinching.”
Lack of Squad Overhaul Post-2018:
After Tottenham’s third consecutive top-three finish in 2017–18, Levy’s failure to refresh the squad or sell underperforming players led to stagnation. No signings were made in the summer of 2018, a decision that contributed to Pochettino’s eventual exit and a decline in performance.
Levy’s focus on financial stability and infrastructure, while successful (e.g., the £1bn Tottenham Hotspur Stadium and state-of-the-art training ground), often came at the expense of on-field ambition. Fans accused him of prioritising commercial ventures like NFL games, concerts, and real estate projects over investing in the squad to compete for major trophies. Only two trophies were won under his watch: the 2008 League Cup and the 2025 Europa League.
His hard-headed negotiation style, while effective for deals like the stadium, frustrated fans who felt it limited Tottenham’s ability to secure top talent or pay competitive wages, hampering their ability to challenge for the Premier League or Champions League.
Fan Relations and Public Perception:
Levy’s reluctance to engage publicly fuelled perceptions of aloofness. In a 2023 Q&A at Cambridge, he expressed hope that fans would see him as acting in the club’s best interests, but his silence often left him disconnected from a fan base chanting for his exit. Protests, including those by the Tottenham Hotspur Supporters’ Trust and Change for Tottenham, highlighted dissatisfaction with his leadership.
His involvement in the European Super League talks in 2021, despite fan backlash, further strained relations. While Levy defended the decision as being in the club’s interest, it was seen as a betrayal of football’s values.
Sacking Ange Postecoglou After Europa League Success:
The decision to sack Postecoglou in 2025, shortly after delivering the Europa League, was particularly contentious. Despite a poor league position (17th), fans felt the move undermined a manager who had restored an attacking identity and connected with the fan base. The financial cost of paying out Postecoglou’s contract and hiring Thomas Frank from Brentford added to criticisms of Levy’s decision-making.
Context and Achievements
Levy’s tenure wasn’t without significant successes:Infrastructure: He oversaw the construction of a world-class £1bn stadium and a top-tier training ground, elevating Tottenham’s global brand and financial status (valued at £2.6bn by Forbes in 2025, up from £80m in 2001).
Financial Stability: Tottenham became the ninth-richest club globally, with £512m in annual revenue by 2023–24, per Deloitte’s Money League. Levy’s diversification into non-football ventures (e.g., NFL, concerts, real estate) bolstered the club’s finances.
Competitive Consistency: Under Levy, Spurs achieved European qualification in 18 of 20 seasons, a stark improvement from the mid-table side he inherited.
Europa League Win:
The 2025 triumph was a rare highlight, though it didn’t fully quell fan unrest.
Some praised Levy for transforming Tottenham into a Champions League regular and building elite facilities, arguing that the Europa League win wasn’t the sole measure of success. Others, like those on Reddit, labelled him a “football-hating scumbag” who prioritised profit over trophies, pointing to the club’s history of selling stars like Harry Kane and Gareth Bale. BBC Sport’s Phil McNulty noted that Levy’s off-field successes would always be overshadowed by on-field failures, with fans prioritising trophies over infrastructure.
Why These Mistakes Mattered
Levy’s mistakes—particularly in managerial hires, transfer strategy, and fan engagement—contributed to a perception that Tottenham underachieved relative to their financial and infrastructural potential. The “Spursy” label, as Giorgio Chiellini famously put it, captured a club that came close but rarely won, with Levy’s cautious approach and frequent managerial turnover (14 permanent managers under his watch) seen as key culprits. His departure, reportedly forced by the Lewis family’s Tavistock Group after a 2025 review, reflected a desire for a new approach focused on “sustained sporting success.”
Critical Perspective
While Levy’s business acumen is undeniable, his prioritisation of financial stability over bold footballing decisions often left Tottenham short of its potential. The narrative of “almost” winning—Champions League final in 2019, near-title challenges under Pochettino—underscores a failure to capitalise on key moments.
His defenders argue he operated with “one hand tied behind his back” due to limited funds compared to state-backed rivals, but critics counter that his reluctance to loosen wage caps or invest decisively in the transfer market exacerbated on-field stagnation.
The sacking of fan-favourite managers like Pochettino and Postecoglou, coupled with ill-fitting appointments, suggests a lack of coherent footballing vision, which ultimately cost him his role.
