If that isn’t enough of a sign of the times, Tottenham Hotspur have just beaten Chelsea in extra time to win the Carling Cup.
Fourteen years later, the Lilywhites are yet to lift another trophy, which begs the question: what has happened to Tottenham?
While it is tempting to make the blanket statement that Spur’s recent form has been uniformly poor, citing some embarrassing results and underwhelming cup runs, this would not tell the full story.
The story of Tottenham’s recent history can be characterized as one of missed opportunities, poor business, and simply being ‘spursy’.
Spurs have had plentiful opportunities to change their fortunes, achieving nine top-five finishes in the Premier League and competing in Europe in thirteen of the last fourteen years.
However, when discussing Spurs, every pro comes with a handful of cons. In 14 years, Spurs have lost four cup finals, had several awkward results against lesser sides, and burned through ten managers, none of whom could reverse the club’s fortunes.
The fact that proven managers such as Jose Mourinho, Antonio Conte, and Maurizio Pochettino have been unable to succeed with Spurs points to a deeper lying issue at the club which goes beyond on-field performances.
Following a recent 1-0 loss to Burnley, a frustrated Antonio Conte threatened to abandon his position as manager, stating post-match that he is “too honest to close my eyes and continue.”
Conte faces the same challenges as predecessors, faced with a squad that is difficult to motivate and often outlast lackluster coaches. Working with names such as Harry Kane and Son Heung Min under a board unafraid of investing seems like a fantastic deal on paper, however, it is a mountain that Jose Mourinho, Mauricio Pochettino, and Nuno Espirito Santo have all failed to summit.
The blame for Tottenham’s recent struggles often falls on Chairman Daniel Levy. Hailing from Essex and Cambridge educated, Levy made his million as a businessman, working with Rangers FC, Slavia Prague, and FC Basel before becoming a majority shareholder at Tottenham Hotspur in 2000.
Levy has not shied away from investing in the team, spending over £1.2 billion on transfers across 22 seasons. The quality of the transfers often let him down. His £54 million record signing, Lyon midfielder Tanguy Ndombélé, has rather consistently underperformed, amassing more yellow cards (10) than assists (9) in his first two seasons at the club before heading back to Lyon on loan in January.
Some particular lowlights of Levy’s transfers can be found in his sales rather than his purchases. Gareth Bale and Luka Modric departed for Real Madrid in 2013 and 2012 respectively and have gone on to win four Champions League titles each.
The same applies to Kyle Walker, who spent eight years at White Hart Lane before a move to Manchester City in 2017, where in four seasons he has won as many trophies as Tottenham have in the last 59 years (10).
While Levy has managed some clever finds in the bargain bin, there is no getting around the fact that he has squandered massive money on several flop transfers, leaving the club £480 million in the red from transfers alone, not to mention the brand-new Hotspur Stadium, which is reported to have cost upwards of £1 billion.
So, how to sum up Tottenham Hotspur’s last fourteen years? Billions of pounds invested, eight managers sacked, four cup finals lost, one shiny new stadium and zero trophies. Despite their brushes with success, Spurs remain spursy and seem set to stay that way for years to come.