When discussing Tottenham Hotspur’s prolonged absence from lifting silverware, it is impossible to overlook Daniel Levy’s tenure.
While the Spurs chairman has built a reputation as a shrewd businessman, his decisions as a football custodian have often drawn ire from fans. Could his leadership be the root cause of Spurs’ barren spell?
Tottenham’s trophy cabinet under Levy
Tottenham Hotspur, once celebrated for their domestic and European exploits, have seen their silverware tally stall under Daniel Levy. Since his appointment as chairman in 2001, Spurs have lifted only one major trophy: the League Cup in 2008, under Juande Ramos. This drought is particularly glaring given that Levy has overseen 12 permanent managerial appointments, with renowned names such as Jose Mourinho and Antonio Conte among them, alongside interim caretakers.
While Spurs have flirted with success, they have fallen short at critical moments. Their run to the 2019 Champions League final under Mauricio Pochettino was inspiring, but it ended in heartbreak with a 2-0 defeat to Liverpool. Similarly, in 2021, they reached the Carabao Cup final, only to succumb to Manchester City. These near-misses have left fans questioning the club’s inability to get over the line.
Many point to Levy’s reluctance to invest in the squad when it matters most. This criticism was especially prominent during Pochettino’s tenure, where a promising Spurs side that consistently finished in the Premier League’s top four seemed just a few marquee signings away from glory.
A tale of missed opportunities
Levy’s era at Tottenham is a paradox; while he has elevated the club commercially, his footballing decisions have arguably held them back. Despite his flaws, Levy has proven himself a capable businessman, constructing a state-of-the-art stadium that generates significant revenue. However, it is his reluctance to adequately invest in the squad during key moments that rankles with supporters.
Pochettino’s reign is a prime example. Under his guidance, Spurs played some of their finest football in decades, regularly finishing in the top four. Yet, during this golden era, the club failed to invest heavily to strengthen the squad. Comparisons have been drawn to Liverpool, who bolstered their team after a fourth-placed finish and were rewarded with Champions League and Premier League titles.
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Another decision that remains a point of contention is Levy’s choice to sack Mourinho just days before the Carabao Cup final in 2021.
With Ryan Mason—a managerial novice—thrust into the spotlight against Pep Guardiola’s Manchester City, the outcome felt inevitable. Fans still struggle to comprehend the timing of this dismissal and what it achieved beyond further disruption.
That said, Levy has sought to instil a winning mentality through his managerial appointments. Names like Mourinho, Conte, and now Ange Postecoglou highlight his intention to bring experienced winners to the club. Postecoglou has reinvigorated Spurs with an attractive, attacking style, but his success will largely depend on Levy’s willingness to provide the necessary backing in upcoming transfer windows.
Is Levy to be blamed for Spurs’ trophy drought?
It is undeniable that Levy has played a significant role in Tottenham’s long wait for silverware. Time and again, Spurs’ managers have appeared to do their best with the resources made available to them, yet the lack of trophies persists. When managers like Mourinho and Conte—serial winners with extensive track records of success—fail to deliver at Spurs, the focus inevitably shifts to the hierarchy.
Both Mourinho and Conte arrived at Spurs with expectations of instilling a winning mentality, yet neither could overcome the structural challenges posed by the club’s limited squad depth and lack of timely reinforcements.
These failures cannot be solely attributed to the managers, as their histories at other clubs demonstrate their ability to deliver when adequately supported.
That said, Levy has an opportunity to redeem himself. Ange Postecoglou’s start at Tottenham has rekindled hope among fans, with the team playing some of its best football since Pochettino’s tenure.
The question now is whether Levy will provide the consistent backing needed to help Postecoglou build a team capable of challenging for silverware. The early signs do look promising as Ange has spent €376,950,000 on transfers since joining the club last summer.
However, the January transfer window and subsequent transfer periods will be critical. By ensuring that Postecoglou has the resources to strengthen the squad, Levy could finally break the cycle of near-misses and missed opportunities.
His legacy at Tottenham may hinge on whether he learns from past mistakes and embraces a more ambitious approach to investment in the team.