David Squires reflects on Daniel Levy’s 25-year tenure at Tottenham Hotspur through a series of satirical cartoons. The cartoons touch upon the managerial changes, transfer dealings, the new stadium, and the unfulfilled quest for trophies, capturing the complex legacy of Levy’s time at the club.
As Daniel Levy steps down from his long-held position at Tottenham Hotspur, ending a reign that spanned a quarter of a century, cartoonist David Squires casts a humorous eye back at some of the most memorable moments, decisions, and, let's face it, occasional controversies that defined his time at the club.
Squires, known for his satirical takes on the world of football, doesn't hold back in this illustrated retrospective. From the revolving door of managers to the sometimes perplexing transfer dealings and the constant pursuit of that elusive silverware, no stone is left unturned. The cartoon series captures the rollercoaster ride that Tottenham fans have endured under Levy's leadership, a period marked by both undeniable progress and recurring frustration.
One recurring theme throughout Levy's tenure has been the pursuit of managerial perfection, or at least, someone who could finally deliver the trophies that Spurs fans crave. Squires aptly depicts the long list of managers who have graced the Tottenham dugout, each promising a new dawn, but ultimately falling short of the ultimate goal. From Glenn Hoddle to Mauricio Pochettino, each managerial era is given a Squires-esque twist, highlighting the highs and lows, the tactical masterclasses and the puzzling defeats.
The transfer market has always been a source of fascination and frustration for Tottenham fans. Squires delves into some of the more memorable transfer sagas, both successes and failures. The arrival of stars like Gareth Bale and Luka Modrić brought moments of genuine excitement, while the departures of key players often left fans wondering what might have been. And then there were the signings that simply never seemed to click, players who arrived with high expectations but failed to make a lasting impact.
Of course, no reflection on Levy's time at Tottenham would be complete without mentioning the new stadium. The state-of-the-art Tottenham Hotspur Stadium is a testament to Levy's vision and ambition, a world-class venue that has transformed the matchday experience for fans. Squires acknowledges this achievement, while also gently poking fun at the financial implications of such a massive undertaking.
But perhaps the most enduring legacy of Levy's reign will be the constant quest for that elusive trophy. Despite reaching the Champions League final and consistently challenging for a top-four spot, Tottenham have struggled to break their trophy drought. Squires captures the agony and the ecstasy of being a Spurs fan, the unwavering belief that success is just around the corner, even when history suggests otherwise.
As Levy departs, Tottenham fans will undoubtedly reflect on his legacy with mixed emotions. He leaves behind a club transformed, both on and off the pitch, but also one that has yet to fully realize its potential. Squires' cartoon series serves as a fitting tribute to a complex and often controversial figure, a man who dedicated a significant portion of his life to Tottenham Hotspur.
You can buy copies of David’s cartoons in the Print Shop and David’s latest book, Chaos in the Box.
Here are some of the cartoons:








