It may just be now or never for Harry Kane and Manchester United.

There has been no end of forced flirtation between them down the years, most of it exclusively in the transfer gossip columns. You also just know that if Sir Alex Ferguson had stuck around for a few more seasons, he’d probably have been at Old Trafford long ago. He had ‘Fergie signing’ written all over him – don’t ask me why, he just did.

This summer, though? It suits both parties, and Tottenham could even be inclined to slightly soften a traditionally hard-line stance around the sale of their captain. It may transpire that they are finally forced to consider selling him as he enters the final year of his contract, or face the prospect of receiving not a penny for one of their all-time greats.

To see him renew again would come as a real surprise given recent events and a hugely uncertain future outlook. If you have somehow failed to keep up to speed with the latest car crash at Tottenham: they have just sacked a caretaker manager and the players offered to reimburse the travelling fans who sat through a 6-1 annihilation at Newcastle on Sunday.

Kane’s dream has been to win major silverware at his boyhood club, but it is one that must feel away than ever. He will be 30 in July, and although that’s no retirement home age these days, time is running out.

He has shown Tottenham commendable loyalty, despite the knowledge he would fit into most forward lines at most elite clubs. He appeared destined to join Manchester City in summer 2021, and even made public his desire to seek a new challenge. But the situation petered out into nothing, with Pep Guardiola later claiming that Spurs refused to even come to the negotiating table.

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Chairman Daniel Levy has, over the years, earned a reputation as a man who drives the hardest of bargains, so perhaps he is the real reason why Kane has never departed North London. Whatever the explanation, how he chooses to handle any potential approach for his club’s skipper this summer will certainly be pivotal.

Levy will not want Kane to sign for a Premier League rival, which is why a bid from Old Trafford will surely have to carry a significant premium to even convince him to pick up the phone. And Kane will know that if he truly intends to leave then he will have to push for it himself, probably in public, because Spurs will be desperate to save as much face as possible. By putting the onus on Kane to spell out his intentions and risk becoming the villain, they can at least present it to fans as ‘well, what else could we do?’

For United, they will know this path is fraught with danger. Or, at least, they should.

Regardless of his contract situation, Tottenham will still hold out as long as possible for as much money as possible. Under the Glazers’ ownership, United have too often been drawn into the protracted pursuit of ultimately unattainable targets, and that inevitably leads to a panic late in the window. Fans were left apoplectic last summer by the months-long courting of Barcelona’s Frenkie de Jong when it was abundantly clear to everyone except United that the Dutch midfielder did not want to leave Spain for Manchester.

The potential for such a situation to arise with Kane is high, albeit with roles reversed. They may feel they can leverage the player’s contract situation into getting a lower price, but it will not be lost on Spurs that United’s need for a striker is borderline desperate.

They were forced to sign the limited Wout Weghorst on-loan in January just to make it to the summer, where there is a decision to be made on a reliably unreliable Anthony Martial, posted missing again as United crashed out of the Europa League in disastrous fashion in Seville last week.

The Frenchman is an infuriating figure; abundantly talented but with a tendency to wilt when the pressure is on, not to mention his consistent struggles with injury and fitness.

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It has been reported that manager Erik ten Hag is sold on Kane as the man to lead his attack, and he has achieved enough this season that United should stand ready to back him to the hilt with whatever he requires over the summer. But while he could really do with a quick resolution on his team’s problem position, you feel that just will not happen with Kane.

Prepare for plenty of ‘United insist they will not overpay’ and ‘Tottenham adamant Kane is not for sale’ over the coming weeks and months, with fans being whipped into a social media frenzy that lasts all summer. It is a tricky one for both clubs – United need a strong window to kick on but putting all their eggs in the Kane basket could blow up in their faces at any moment. Should they fail to get him and turn their attention to alternatives, selling clubs will have already seen their hand, know their need is dire and bump up prices accordingly.

Tottenham, meanwhile, have a new manager to appoint and could take the view that punting their star striker is hardly the best way to kick off a new era. They have shown in the past they are prepared to hold firm even if Kane proclaims he wants to be sold, and do not necessarily need the money.

It could, in the end, come down to whether Levy is prepared for him to leave on a free in a year’s time. That may be a preferable option to being forever known as the man who sold Harry Kane. Although the forward wanted to leave in 2021, he was not prepared to trash his Tottenham legacy to make it happen, and the club may just take a gamble on that being the case again this summer.

That it is only April and this has all the makings of a ‘saga’ feels rather ominous. Will we still be having this same discussion in August? I wouldn’t bet against it.