When a Des Walker own goal gave Tottenham Hotspur the 1991 FA Cup title, it meant the north London side became the first team in the country to life the trophy eight times. Winning silverware was very common for Spurs, a tradition that started under manager Bill Nicholson. In his sixteen-year tenure, he guided the club to eight trophies, including European success in the Cup Winners' Cup and UEFA Cup as well as their second, and last, league title in 1961.
For the 1981 FA Cup final, the Tottenham squad, with the help of musical duo Chas & Dave, released the single "Ossie's Dream (Spurs Are on Their Way to Wembley)". It reached number five in the charts and Spurs lifted the trophy after a replay against Manchester City in which Ricky Villa scored his famous solo goal. The lyrics are revealing to how Tottenham were thought of as a club. "Spurs are on their way to Wembley,/Tottenham's going to it again," and "The Kings are claiming their crown". This was a club that was renowned for winning trophies.
Since that record FA Cup win, however, Tottenham have won just two trophies as they languished in mid-table: the League Cup in 1999 and 2008. From the late 2000s, Spurs have progressed to a Champions League side but another trophy for Daniel Levy has remained elusive. They reached the League Cup semi-final in 2019 but Chelsea won on penalties and the final in 2009 and 2015 but lost to Manchester United and Chelsea again.
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| Harry Kane has not won a major trophy in his career. Photo by Enviro Warrior |
They reached the FA Cup semi-final in 2010, 2012, 2017 and 2018 but never got to the final. A second-place finish in the league in 2018 and coming third in the season when Leicester triumphed, as well as the failure in cup competitions, has added to the idea that Tottenham lack the mentality required to turn into a team capable of winning trophies.
Mauricio Pochettino oversaw Tottenham's run to the Champions League final in 2019 but that again ended in defeat. He was dismissed shortly after and Levy turned to Jose Mourinho, a man that prides himself on his stacked trophy cabinet.
Mourinho may have reached the Carabao Cup final but on Monday, he was sacked due to poor results in the league. Tottenham are now 6th after a 2-1 win over Southampton in Ryan Mason's first match. His second is their first domestic cup final in six years. This match takes on greater importance not only for Tottenham to win a trophy but in light of Harry Kane wanting to leave.
Kane is unlucky to find himself in this Tottenham era. He is arguably the best striker in the world but he has not got the same material reward for his goal-scoring exploits. With Kane's recurring ankle problems that may see him out of the final and aged 28 in June, it is hard to see why a club like Manchester City would buy him for £150 million ahead of Erling Haaland, 20, or Kylian Mbappe, 22.
Winning the Carabao Cup won't satisfy Kane, though. A player of his quality should be challenging for league titles, not trying to scrape top four. He effectively made himself a prisoner by signing a six-year contract in 2018. With three years left, Levy has all the power and would be unwilling to sell.
If he stays at Tottenham, which seems the most likely option, Kane may never get the silverware he craves but will be remembered for his goals. He has a better Premier League goalscoring ratio than Alan Shearer and is 57 goals behind Jimmy Greaves to become the club's record goalscorer.
Greaves played for Tottenham between 1961-70 scoring hundreds of goals and, crucially, winning trophies: two FA Cups and the Cup Winners' Cup. The Carabao Cup would be great for Kane to win but it does not show that Tottenham will start winning trophies regularly, which may force Kane to force a move away.
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