Harry Kane will be 28 in July and he faces a massive career decision this summer.
Does he stay loyal to Tottenham, where he stands every chance of breaking Alan Shearer’s record as the Premier League’s top scorer – or does he move to a club who can offer him a likelier route to trophies and winners’ medals?
After a dreadful week in Spurs’ season, the England captain must be tempted to jump ship while he is still in his prime.
First, a confession. I have to admit how massively wrong I got it four months ago, when Tottenham beat Manchester City to go top of the table and I tipped them to win the title.
But I can’t understand how a side with Kane, Heung-min Son and Gareth Bale up front, all the midfield protection you could ask for and a World Cup-winning goalkeeper, can now find themselves six points off the top four.
And it beggars belief that, from front-runners in November, Spurs are now chasing probably one Champions League spot with Chelsea, West Ham, Liverpool and Everton.
Inevitably, the speculation about Jose Mourinho’s job as manager will be ramped up after Tottenham’s awful Europa League defeat by Dinamo Zagreb on Thursday night.
It was a disgraceful performance, but in hindsight Spurs have had that in their locker all season.
Remember when they lost a group match in Antwerp and Mourinho posted a photo on social media of himself sulking on the team bus?
But what happens over their last 11 games this season will not just determine Mourinho’s future. It could impact massively whether Kane stays or leaves.
If Tottenham win the League Cup and finish in the top four, I would argue that’s a decent season and a platform to build further success.
But the lack of intensity, the lack of cohesion, the lack of sheer desire in both the north London derby and in Zagreb the other night does not fill me with optimism that either target will be met.
And for Kane, the dilemma is greater than ever because he has serious competition as the most-coveted striker in Europe now.
If Spurs win the League Cup but finish outside the top five, instead of Champions League football, he could be involved in the new third-tier Europa Conference League next season.
Honestly, I think Kane deserves better than a third-tier competition.
So if Manchester United or one of the continent’s big guns comes calling this summer, can he afford to turn them down if he wants his career to be fulfilled?
Erling Haaland has probably overtaken Kane as first-choice target for Europe’s elite, so he faces a stark choice.
He can stick around at Tottenham, break Shearer’s record, cement his place as a Spurs legend and take his chances that a medal or two might come his way.
Or if his old boss Mauricio Pochettino at Paris Saint-Germain, Real Madrid or Manchester United come calling, does he want to be a winner – and have the medals to show for it?
United have not won anything for four years, but the way they managed a tricky away leg in the San Siro to beat AC Milan was miles ahead of Tottenham’s disarray in Zagreb.
I’ve said before that United are a top-class centre-forward away from being truly frightening, so I’ll say it again.
If he can’t get Haaland, new director of football John Murtough should go all-out to bring Kane to Old Trafford. Move heaven and earth for him.
Just imagine a front five of Kane, Rashford and one of Mason Greenwood, Anthony Martial or Daniel James, with Bruno Fernandes and Paul Pogba behind them.
They would take some stopping.
I’m not trying to hustle Kane out of the door in north London – it’s his career, his decision, his legacy, not mine.
But it would be a crying shame for a player of his talent, and one of the great strikers of any era, to have no medals to show for all those goals.
And losing Kane would be the most serious collateral damage of Tottenham’s latest season where they flattered to deceive.