Tottenham talisman Kane finds himself at a crossroads

English football’s biggest star faces a tricky choice this summer after last year’s transfer saga. Does he leave his boyhood club in a bid to win trophies or keep faith with Conte-managed Spurs?

Is Harry Kane the best modern-day footballer never to have lifted a trophy?

It’s an impossible question to answer, for any evaluation of ‘best’ is subjective. But he certainly is among the most prolific scorers without silverware — he has notched up more than 300 goals in his professional career, for club and country. He is also arguably the most high-profile owner of an empty trophy cabinet, given that he is England captain and one of the leading lights of the Premier League as Tottenham Hotspur talisman, both of which guarantee him plenty of media attention.

Kane has come close to hoisting a cup in celebration. He has twice finished on the losing end of a League Cup final. The 2016-17 Premier League season saw Tottenham rack up an impressive tally of 86 points and still end up seven behind champion Chelsea. Kane has also suffered heartbreak in Europe, for club and country: with Spurs in the Champions League final, against Liverpool in 2019, and two years later with England in the final of the Euros, against Italy.

Perhaps most disheartening for Kane has been the fact that his time at Spurs has been among the club’s brightest periods in recent history. When former manager Mauricio Pochettino was masterminding a modern, high-energy style, Tottenham fans had every reason to dream big: the football was eye-catching; Spurs were frequently going toe-to-toe with the best.

There was a genuine feeling among supporters that there had been a power shift in North London away from Arsenal and that Spurs were now poised to join the Premier League’s elite on a consistent basis. The feeling was backed up by the league table, as Kane’s Spurs began to finish above the Gunners. But the period also saw Arsenal win four FA Cups (and four Community Shields) — and it’s hard to reassure yourself of a power shift when your bitter city rival adds to its much larger trophy cabinet, that too during a period when it is noticeably slipping.

Given this context, it’s understandable why Kane’s future has become one of the biggest stories in world football — a story that has had plenty of play since last summer when he indicated that he was frustrated at Spurs. “[2020-21] has been a disappointing season if I am totally honest. We have had so many opportunities and we haven’t quite got over the line. I want to be winning the biggest prizes and we are not quite doing that,” he said.

Sky Sports reported last summer that Kane had informed the club of his desire to leave, adding that Manchester United, Manchester City and Chelsea had been in touch with his representatives. The 28-year-old was a major target for City, but an initial bid — reportedly worth £100 million — was not enough for Tottenham to let him go and City was reluctant to meet Spurs chairman Daniel Levy’s reported asking price of £160 million. The transfer saga dragged on all summer, with the ‘will he, won’t he?’ speculation reaching fever pitch.