Daniel Levy’s Tottenham – 24 Years of Failure

When Daniel Levy took control of Tottenham Hotspur in February 2001, there was optimism that the club would finally break into English football’s elite after decades away from the top. Over two decades later, that optimism has been destroyed by repeated failure, poor decision-making, and a mentality that has seen Spurs become synonymous with falling short when it matters most.

One League Cup in 24 years is the sum total of his reign. And the worst part? Nothing looks like changing.

Levy’s tenure began amid turbulence. A revolving door of managers followed, with Spurs cycling through Glenn Hoddle, David Pleat, the brief and disastrous reign of Jacques Santini, and Martin Jol, before Juande Ramos delivered silverware in 2008 with a 2-1 win over Chelsea in the Carling Cup final – Tottenham’s first trophy since 1999.

It should have been a stepping stone, a platform for greater success. Instead, it became little more than an anomaly.

Ramos was dismissed the following season, and in came the popular Harry Redknapp. Redknapp revitalised Spurs, and with a squad brimming with talent – including Gareth Bale, Jermaine Defoe, Luka Modric, and Ledley King – he propelled them into the Champions League for the first time. However, just as the club appeared to be on the right path, Levy’s mismanagement reared its head once more. Redknapp was sacked in 2012, despite leading Spurs to a second consecutive fourth-place finish.

Andre Villas-Boas and Tim Sherwood were next to come and go, before Mauricio Pochettino’s arrival in summer 2014. He built an exciting, young team that played some of the best football in Europe and led Spurs to a League Cup final in his first season, ultimately losing 2-0 to Chelsea. But, once again, Levy’s lack of ambition proved costly. In 2016-17, Spurs finished second the Premier League with a club-record 86 points yet failed to strengthen the squad adequately.

Levy went one step further in 2018. After a third-place finish and a second consecutive FA Cup semi-final defeat, Tottenham made history by becoming the first Premier League club ever to fail to make a signing in the summer transfer window. This left Pochettino with an ageing and depleted squad at a time when they were so close to glory.

Spring 2019 saw the grand opening of Tottenham Hotspur Stadium. Labelled as a game-changer by those at the top of the Tottenham tree, the focus drifted well away from football. While rivals invest heavily in their squads, Levy’s priority has been commercial expansion.

The club has prioritised NFL partnerships, boxing events, concerts, and even a rooftop Skywalk over investing in the team. Beyoncé, Guns N’ Roses, and the NFL have all been welcomed with open arms, while world-class footballers remain an afterthought.

The irony is that success on the pitch would drive even greater revenue off it, yet Spurs continue to chase corporate deals rather than trophies. The fans, who pay the highest ticket prices in Europe, have been left with a team incapable of delivering when it matters most.

Then came the 2018-19 Champions League run. Spurs defied all odds, pulling off unthinkable results against Manchester City and Ajax. Tottenham had reached the biggest game in their 137-year history. But yet again, when the moment arrived, they froze. A limp 2-0 defeat to Liverpool, mustering just three attempts on target despite trailing for 87 minutes, was a crushing indictment of Tottenham’s inability to turn promise into success.

That should have been the catalyst for Levy to act, providing Pochettino with the tools to build on a remarkable run. Instead, the infamous summer window that saw the high-profile signings of Tanguy Ndombele and Giovani Lo Celso was marred by classic Levy deals, with youngsters Ryan Sessegnon and Jack Clarke arriving from the Championship. Within months, the squad had grown stale, and Pochettino was sacked.

The next throw of the dice was to bring in serial winners. First Jose Mourinho, then Antonio Conte. Both arrived with glittering CVs, both left furious at the club’s lack of backing. Mourinho reached the League Cup final in 2021 only to be sacked six days before the clash with Manchester City – a decision that epitomises Levy’s leadership of the football club. Ryan Mason stepped in, and Spurs, predictably, lost.

After the three-month (failed) experiment with Nuno Espirito Santo, Conte’s tenure followed a similar script. After early promise, taking Tottenham back into the Champions League, the Italian became the next manager be axed after his pragmatic, defensive approach failed to win over the fans, or win football matches. Conte’s final act was to launch a brutal public attack on Levy and the club.

Aiming at the man at the top, Conte expressed, “They’re used to it here. Don’t play for something important. They don’t want to play under pressure. They don’t want to play under stress. Tottenham’s story is this. 20 years there is the owner and they never won something. Why?”

His words grow more accurate by the day.

And then there’s the Harry Kane saga. Levy refused to sanction his sale when Manchester City came knocking in 2021, only to sell him two years later, one day before the start of the season, to Bayern Munich without securing a proper replacement.

Spurs started the 2023-24 season without their greatest-ever goal scorer, once again highlighting the lack of forward planning that has plagued this club for decades.

Fast forward to the present day, and Tottenham remain a club trapped in the same cycle of failure. Ange Postecoglou started brightly, but a promising first ten games quickly unravelled. Injuries have decimated the squad, exposing the lack of depth caused by years of mismanagement. Many questioned for years how Spurs would cope without Kane. The answer is becoming clearer by the day.

Last night’s Carabao Cup semi-final defeat to Liverpool was just the latest chapter in this ongoing horror story. Outclassed, outfought, and ultimately beaten with minimal resistance - it was a script Spurs fans have seen time and time again.

Postecoglou will likely be sacked soon, and a new manager will come in. That new manager will start brightly, encouraging fans, before being left short in the transfer market and on the pitch, crashing out of the cups, and in a couple of seasons’ time Spurs fans will be discussing who they want as their next manager after Levy pulls the trigger again.

Since 2001, Tottenham have lost five FA Cup semi-finals, four League Cup finals, and four League Cup semi-finals. No club in England has lost more high-pressure games in the last 20 years. The numbers don’t lie: Tottenham don’t have a winning mentality, and under Levy, that won’t change.

For all the talk of financial growth, a state-of-the-art stadium, and record revenues, Levy’s reign has been an abject failure where it truly matters - on the pitch. The best managers in the world have come and gone, yet the same weaknesses remain. Big games arrive, and Tottenham crumble. Leadership is non-existent, experienced players disappear, and the squad remains riddled with mental fragility.

As long as Daniel Levy remains in charge, this club will never truly succeed. One League Cup in 24 years – that is Tottenham Hotspur. Always close, always collapsing, always failing. Nothing will change until genuine ambition replaces the mediocrity that has characterised this era of endless disappointment.

But at least there’s the Skywalk, right?