The curious case of Tottenham Hotspur: Serial bottlers or punching above their weight?

When ‘Mr. Tottenham Hotspur’ himself, Ledley King, led his teammates up the stairs of the new Wembley to lift the League Cup in 2008, there was a wave of optimism among the Spurs fans that their beloved North London club could challenge the established order. Since the turn of the millennia, the coveted ‘Top 4’ of the Premier League remained almost like a distant dream to the rest of the Premier League. Manchester United under Sir Alex Ferguson held a near monopoly of Premier League titles while Arsenal under Arsène Wenger and Chelsea under various managers also found success, while Liverpool managed to finish at least fourth. This era was under threat when Sheikh Mansour bought Manchester City in 2008, but it wasn’t the billions of the Emirati Royal that finally broke the fabled top 4. It was, in fact, a boisterous Spurs side, managed by the wily veteran Harry Redknapp, that became the first club in years since Leeds United to break into the coveted ‘Top 4’. It was almost poetic that the final top 4 places was decided between a match against Spurs, on a modest budget, versus the big spenders, Manchester City.

The challenge for Spurs was not whether they could push on and aim bigger, a title challenge for instance. Because City, Chelsea, Manchester United, Arsenal, and Liverpool had resources that Spurs could only dream of. Spurs Chairman Daniel Levy, who is still infamous for being a shrewd operator, negotiated a few deals that raised a few eyebrows. Future Real Madrid stars Luka Modrić and Gareth Bale were among these signings that Levy orchestrated, despite criticism by sections of the media questioning the calibre of both players. They would eventually be revered as generational talents who ended up winning every major trophy at club level, but only after they left Spurs for record transfer fees. Gareth Bale’s transfer of around £90 million from Spurs to the Spanish capital was the world record at the time – more than what Real paid Manchester United for the services of a certain Cristiano Ronaldo in 2009.

Bale’s departure was certainly a blow for Tottenham, but Levy was given the opportunity to invest in his squad and match the spending power of their rivals. The club brought in up to seven new players for their new manager, André Villas-Boas, who was widely revered as the second coming of the ‘Special One’ himself, José Mourinho. Unfortunately for Levy and his charismatic young manager, only one of their seven new signings would go on to find success at the club, and it was none other than the magical midfield maestro, Christian Eriksen. It is almost ironic that Eriksen would depart Spurs a few years later, win the Scudetto with Inter, almost literally die on the pitch while on international duty with Denmark, revive his career in England and win a trophy with Manchester United in 2023, while Spurs are yet to win a trophy since 2008.

It would be harsh to judge Spurs on how almost all of their former stars ended up finding success elsewhere because winning a trophy in England requires a bit of fortune as well. Obviously, Villas-Boas would eventually be sacked after a poor run of results. But his replacement, Tim Sharewood was also unable to turn things around. But Sherwood’s successor would bring much joy and hope to the Spurs faithful. Mauricio Pochettino joined Spurs from Southampton as the new manager and it coincided with the rise of a player whom none of his coaches believed would find success in the top flight. And that player is the current England captain, Harry Kane – England’s all-time leading goal scorer and second-highest goalscorer in Premier League history. Spurs spent millions to find a goal scorer, and it was one of their own from their academy who stepped up and delivered. 2016-2019 were arguably Spurs’ best years since the great Jimmy Greaves wore the lily white of Spurs in the 60s.

Pochettino’s team played an attractive brand of football, with the Belgian duo of Toby Alderweireld and Jan Vertonghen at the heart of the defence, Eriksen as the creative lynchpin, and the explosive South Korean Son Heung-min forming a lethal partnership with the Spurs talisman Harry Kane. On their day, they could beat any team, but unfortunately, the new state-of-the-art stadium meant that funds were limited to build a squad with depth that could challenge for trophies. 2016 was the year they should have finally won the Premier League, but the unlikeliest of teams, Leicester City, with the odds of 5000-1 at the start of the 2015-16 campaign, ended up winning the League, in what could only be described as the most unbelieve Premier League campaign ever. Spurs came close yet again the following year, finishing second behind Antonio Conte’s Chelsea.

If one were to ask any football fan which was their favourite Champions League campaign, most neutral fans would say that it is the 2018-19 campaign, and Spurs were at the heart of it. An absolute thriller against Pep Guardiola’s Manchester City in the quarterfinals and an unbelievable comeback against Ajax in Amsterdam, thanks to a second-half hattrick from Lucas Moura, overcoming a 3-0 deficit on their way to the final against Liverpool. The final itself was unfortunately a dull affair, as a timid Spurs fell apart after Mohammed Salah scored from the penalty spot within the first two minutes of the game. The heartbreak of the final was evident on the players the following season, coupled with an ageing defence, and lack of proper investment, Pochettino’s Spurs reign also ended without any trophies despite much promise.

Spurs would eventually go through a few managers including serial winners Jose Mourinho and Antonio Conte. But Spurs became the only club where both managers failed to win a trophy. And quite naturally, the unforgiving world of ‘Football Twitter’ was brutal to the North London club. They became the target of constant ridicule, the term ‘Spursy’ became a word that people describe failures, and Harry Kane, who is comfortably one of the most complete footballers today, became the symbol of the club’s failure. Kane’s talent is undermined because he does not have a winner’s medal to his name. Daniel Levy must shoulder some of the blame, sacking Mourinho days before the League Cup final was shortsighted. Whereas hiring Conte, who had reportedly declined the job a few months before his appointment was bordering on absurdity.

Conte’s unceremonious departure exposed Tottenham’s downward slide since 2019. They would have to heavily invest in the squad, especially in defence. And if Kane does finally leave for greener pastures, they are losing 30-plus goals a season, and more – something that is almost impossible to replace. But ultimately Spurs were never expected to be title challengers, they were the outliers who threatened the established order, without state-sponsored backing. They harboured the same ambitions as today’s Brighton, Aston Villa, or even West Ham and succeeded in being revered as one of the big clubs – a feat that not even Premier League and FA Cup-winning Leicester City have achieved. One can even draw philosophical parallels from the Greek mythology about Icarus flying too close to the sun.

Managerless Spurs are now much better positioned than Chelsea as they head to the tail end of the season. But Chelsea under the right management could make a surprise comeback next season, Tottenham on the other hand needs significant investment and of course a new manager. It would be a hammer blow for Spurs if former boss, Pochettino, were to sign for London rivals Chelsea. According to the British tabloids, current Bayer Leverkusen boss Xabi Alonso is Tottenham’s number one target to take over the managerial reigns. The former Liverpool, Real Madrid, and Bayern Munich midfielder is quietly establishing himself as a highly sought-after young manager. Another name that is being reportedly discussed at Spurs is the former Bayern Munich boss Julian Nagelsmann. The young German manager reportedly turned down the Chelsea job in favour of a more promising project. Considering Chelsea are in the bottom half, losing six in a row under new interim boss Frank Lampard. Regardless, the next manager at Spurs is stepping into a monumental task, especially if Harry Kane leaves.