Harry Kane faces arguably the biggest summer of his career as he decides on his Tottenham future while Euro 2020 is also on the horizon.
The England and Tottenham star is quite rightly regarded as one of the best forwards in English football.
But he remains trophyless in his career so far, with the latest opportunity passing him and Spurs by in a 1-0 defeat against Manchester City in Sunday’s Carabao Cup final.
Kane’s fitness was a huge topic of conversation ahead of the Wembley showdown after he picked up an ankle injury in a 2-2 draw at Everton last weekend.
Despite that Kane was included in interim boss Ryan Mason’s starting XI – but like the rest of his Spurs teammates failed to have any sort of impact on proceedings.
Remarkably, Kane didn’t attempt a shot or create a single chance for Spurs in Sunday’s final.
That’s the first time he’s done neither while playing more than 45 minutes in a game since September 2018, against Inter Milan in the Champions League.
Trevor Sinclair’s word of warning for Kane on talkSPORT earlier this week was also sadly proven true.
“Harry’s got to be really honest with himself, his teammates and his manager, because I think he’s going to make the decision,” he said on Thursday’s Breakfast show.
“You can forgive him for wanting to play even if he’s not 100 per cent fit, but I think he’ll never forgive himself if he does play and he’s not fit.
“I always say when a player’s got an ankle injury or a knee injury, I take them out to the training ground and say to them ‘if you went in for a 50/50 would your ankle be able to deal with it?’
“I think if he’s honest with himself then he can give a real answer.
“You wouldn’t want him going out there playing and not doing himself justice, Tottenham losing that game and losing out on Harry’s ability for the rest of the season.”
Sinclair also cited the example of Kane not being fully fit for the 2019 Champions League final against Liverpool.
“That experience should give him a good starting point of where he has to start thinking, before he makes the decision,” Sinclair explained.
“It’s a huge call. Silverware is silverware – he wants to be involved – but look at the bigger picture.
“They need to still go for the top four and make it into this Champions League and he needs to be honest with himself and his teammates.”
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Kane’s hopes of playing in Europe’s premier competition next season also look unlikely if he stays put, with Spurs five points off London rivals Chelsea in fourth with just five games remaining.
So it begs the question: Is now the right time for Harry Kane to leave Tottenham?
There’s no doubt he’ll be replaying this question in his mind constantly over the coming months.