Daniel Levy’s departure as Tottenham chairman marks a turning point, with his legacy defined by business success but a lack of trophies. He built a world-class stadium and training ground, but faced fan frustration over restrained spending and missed opportunities for on-field glory. While commercially astute, Levy’s tenure raises questions about prioritizing profits over footballing ambition, especially after coming close to success under Pochettino.
Daniel Levy's departure as chairman of Tottenham Hotspur marks the end of an era, one defined by shrewd business decisions but also by a persistent failure to achieve consistent on-field success. Had it not been for the unwavering focus on footballing glory, Levy might be remembered as one of the Premier League's most accomplished executives. His tenure saw the construction of a world-class stadium, a state-of-the-art training facility, and a diversified business model that incorporated NFL, rugby, boxing, monster truck events and major concerts. He even managed to get Tottenham into the Super League conversations, despite the club's relatively barren trophy cabinet. Yet, despite these achievements, Levy faced constant fan protests, a testament to the passionate but often unyielding demands of the Tottenham faithful.
The announcement of his departure on Thursday sent shockwaves through the footballing world. There were subtle hints that Levy might have sensed the end of his reign approaching. Earlier this year, he declared that "all options are open" in response to growing calls for his resignation. In a rare, extensive interview with Gary Neville last month, he mused, "When I'm not here I'm sure I'll get the credit," suggesting a contemplation of his legacy. At 63, and missing the Uefa Super Cup final to help his daughter settle into university, perhaps Levy was beginning to reassess his priorities.
Tottenham had already begun a process of restructuring. The appointment of former Arsenal executive Vinai Venkatesham as CEO during the summer, coupled with the announcement in March that Peter Charrington, a director of ENIC (which owns 86.91% of the club), would join the board, indicated a shift in approach. Charrington now steps into the role of non-executive chair. The extent to which Levy willingly participated in this succession planning remains unclear, but the Lewis family, who own ENIC, appear to have sought a fresh perspective, although Levy and his family retain a significant 29.88% stake.
A major source of contention for fans has been Levy's financial stake in the club, which naturally incentivized him to prioritize profitability. This, coupled with his status as the highest-paid Premier League chairman, drew criticism from supporters whose primary concern was on-field performance. The reality is that fans still care about winning trophies and playing attractive football.

That dichotomy is perhaps best symbolized by the video montage played before every Tottenham match, celebrating the club's history to stirring music and Danny Blanchflower's famous dictum that "the game is about glory." Yet, the team that emerges onto the pitch often reflects a club operating with a restrained wages-to-turnover ratio.
Levy's caution was, to some extent, dictated by circumstances. White Hart Lane required a significant upgrade, and Levy successfully managed that while ensuring the club remained in its traditional location. This was no small feat in London, where land is scarce and expensive. However, the project came at a cost of at least £1 billion, which, as Arsenal discovered with their move to the Emirates Stadium, inevitably restricts expenditure in other areas.
Conservative spending in the transfer market, coupled with rising ticket prices, fueled fan frustration. During Levy's 24-year tenure, Spurs reached 16 semi-finals and seven finals, finished third twice and second once in the league, but only secured the League Cup in 2008 and the Europa League last season. The question lingers: could they have achieved more silverware with a slightly more ambitious transfer policy? It's not as if profitability and sustainability regulations are what has constrained them.
Two key disappointments stand out. Firstly, the £85 million received from Real Madrid for Gareth Bale was not reinvested effectively. Secondly, the period following the 2017-18 season, when Tottenham finished in the top three for a third consecutive year, proved pivotal. The move to the new stadium occurred towards the end of the following season, culminating in a Champions League final appearance. However, beneath the surface, a sense of staleness had taken root. Tottenham failed to make any signings in the summer of 2018 and, crucially, did not sell the players Mauricio Pochettino believed needed replacing. Consequently, their first full season in the new stadium started poorly, leading to Pochettino's dismissal in November. The appointment of José Mourinho, while seemingly an ambitious move, ultimately proved misguided.
The sense that Tottenham had come so close to something special under Pochettino has inevitably shaped perceptions of what followed. What if Levy had been more willing to take risks? What if he had invested more wisely? When success did eventually return, after a 17-year drought, it arrived in circumstances that made it difficult for Levy to claim credit, having sacked Ange Postecoglou just 16 days after a Europa League triumph.
Assessing Levy's legacy is complex. His vision was overtly commercial, and by those metrics, he succeeded at Tottenham. The club was profitable in 13 of the 15 seasons before the stadium move, and while the current debt of £850 million is substantial, it is understandable given the envy that the stadium generates among other clubs. However, a football club is more than just a commercial enterprise; at some point, the actual football matters. And on that front, Levy's scorecard reads rather less impressively.