Ever since he burst on the scene the best part of a decade ago, all the talk has been about when not if Harry Kane will leave Tottenham.

After originally entering as a ‘one-season wonder’ to many, Kane just kept scoring goals and has gone on to become one of the most lethal goalscorers we have seen in this country. He is currently on track to become the all-time top scorer in the Premier League, while he could conceivably become the greatest scorer in Spurs’ history too if he stays.

All the goalscoring accolades that he has however are marred by the fact he has never won a trophy in his career.

As Spurs look set to finish outside of the Premier League top four positions following a defeat to Manchester United this past weekend, it means they’ll be in the Europa League at best once again next year.

They’ve been eliminated from all competitions so far this season except for the Carabao Cup, but they’re the heavy underdogs as they will face Manchester City in the final at Wembley at the end of the month.

But even if they pulled off an upset and won the trophy, that will surely only increase their talisman’s thirst for silverware. The issue Kane has is that he will still have three years remaining on his contract once the summer window opens, making it incredibly difficult to just up and leave the club.

Kane has always maintained that winning trophies is the most important thing for him before he retires, and as he prepares to turn 28 years old the time has arrived where he now has a big decision to make.

If he decides to stay, he is accepting that trophies are unlikely to follow in a career that is beginning to now enter its final chapter. He’ll be 31 when his current deal ends and with his previous injury history, there is no telling what state his body will be in at that point.

Not to mention, the biggest clubs may have moved on by then. The likes of Erling Haaland, Kylian Mbappe and Joao Felix will all be even further into the development of their careers and likely already be filling the roles at those clubs. If they aren’t, they will surely have leapfrogged Kane in the thinking because of the stage of careers they’ll be in.

Add to that the fact that several top clubs are in need of a striker now, there is no better chance for Kane to leave than this summer.

Man City are letting Sergio Aguero leave the club at the end of his contract this summer, while Manchester United know they need a top level striker regardless of whether Edinson Cavani stays at the club.

While both teams are reportedly prioritising a deal for Haaland, the fact he has a release clause of just €70million that activates in the summer of 2022 may put some teams off spending near double that to get him early.

It makes Kane the prime target, but an asking price of around £120m is likely to be a starting point for negotiations. Kane however is a proven standard of world class footballer. He will hit 20 league goals with his next strike this season, making him the fourth player to do so in five or more seasons along with Alan Shearer, Thierry Henry and Aguero. Add to that the fact he’s also got 13 assists this season so far, a tally no striker other than Henry has ever topped, he is the complete footballer.

The big question is how much does he want to leave? Is he willing to force a move and formally request a transfer, potentially ruining a reputation with fans of the club he grew up with that have supported him through everything in his career?

He should, because he owes them nothing. He stayed when it would’ve been easy to leave, he signed new contracts, he led the club to become a consistent competitor for Champions League football and he never stopped scoring goals.

He’s arguably their best player in modern history, so if he opts to leave to earn himself some silverware to look back on before his career ends it shouldn’t be deemed as a negative on his Spurs career.

They won’t be able to replace him, but that also isn’t his problem. He has to make the decision this summer of whether to stay or go, it really is now or never.