Harry Kane’s protracted move to Manchester City is hurtling towards a decisive phase in the summer transfer window and Tottenham may be powerless to avoid losing their talisman.
The transfer saga took a dramatic twist on Monday when it emerged via Sky Sports News that Kane had failed to report for pre-season training.
Kane, who claimed the Premier League Golden Boot last season with 23 goals, has returned from an extended break after helping England reach the Euro 2020 final.
He was expected to return to the club's Hotspur Way training complex on Monday morning to undergo a Covid test and undertake blood tests, but failed to report for training with new boss Nuno Espirito Santo.
It was a surprising move from a player renowned for leading by example and setting the bar for professionalism, yet it ultimately proves how strong is his desire to leave the club.
The club are believed to be unmoved by Kane’s efforts to leave the club and are preparing to serve the striker with a maximum fine of two weeks’ wages expected, according to Sky Sports.
But with Kane reportedly set to continue his absence with no plans to return, Tottenham now face a dilemma over whether to sell their prized asset.
Mirror Football examine the five key parties involved in brokering the deal if the transfer does go ahead this summer.
Charlie Kane
When choosing his agent to represent his interests, Kane took a different route to some of the stars in the game such as Paul Pogba and Erling Haaland, who are managed by Mino Raiola and Jorge Mendes.
Instead of taking the ‘super agent’ route, Kane kept it in the family and stuck with his brother, Charlie.
His agency, CK66LTD, are responsible for managing Kane’s sponsorship deals with brands such as Nike, Lucozade, McDonald’s and Beats.
The pair are very close, with the Tottenham striker recently taking on the role of best man at his wedding and Charlie was spotted in the crowd supporting his brother at Euro 2020 on several occasions.
Former Arsenal player Perry Groves recently remarked that Spurs were fortunate Kane wasn’t managed by a super agent, suggesting the fallout would have been more dramatic.
Speaking to talkSPORT, he said: “I think you are very lucky he has his brother as his agent. If you had Raiola or one of the other super agents…”
Ironically, Kane’s decision to go AWOL has whipped up a storm in the same manner that a super agent would choose to — whether or not Charlie was behind it, only he will know.
Daniel Levy
In the modern era of football, player power often takes precedence. Players know that if their contract is running down, they can force their clubs into agreeing cut-price fees to seal their moves away.
But when Kane penned his long-term deal in 2018, he effectively signed away his bargaining chip. He still has three years left on his current contract and that gives Tottenham chairman Daniel Levy some power in this battle.
The Spurs supremo has gained notoriety for his hardline negotiation tactics and is rarely taken to the cleaners when it comes to buying, selling and renewing contracts. His £160million valuation of the 28-year-old underlines that.
It has been reported by the Daily Star that Kane believes he has a 'gentlemen’s agreement' with Levy, allowing him to leave this summer if they did not qualify for the Champions League.
Kane even revealed his plans to sit down with Levy to discuss his desire to leave in pursuit of winning trophies.
“For sure, it's a moment in my career where I have to kind of reflect and see where I'm at and have a good, honest conversation with the chairman. I hope that we can have that conversation,” he told Gary Neville on The Overlap.
"I'm sure that he'll want to set out the plan of where he sees it but ultimately it's going to be down to me and how I feel and what's going to be the best for me and my career this moment in time.”
It remains to be seen whether such an agreement was ever made, but Kane’s extreme tactic to force Levy’s hand suggests he will not be living up to his word.
Man City hierarchy
Chairman Khaldoon Al Mubarak has been the right-hand man of billionaire owner Sheikh Mansour since taking over Manchester City in 2008.
So his declaration in May that the club would “send a strong message” and smash their transfer record to sign a top striker this summer was a statement of intent.
Chief executive Ferran Soriano and chief operating officer Omar Berrada are key figures in carrying out City’s duties but Al-Mubarak holds what could be the deciding factor in any deal for Kane.
In addition to their interest in Kane, City are expected to seal the £100m signing of Jack Grealish before the transfer window closes.
Having two complex transfer deals of such a large scale at the same time for most clubs would be near impossible, but as seen over the last 13 years, Man City have demonstrated their endless resources allow them to broker agreements of this kind.
They will need to act fast now Kane has put his Spurs future on the line by refusing to train, with Levy now in a vulnerable position, although fining Kane would certainly put a clock on his act of defiance.
But they have overcome Levy once before in signing Kyle Walker for £49m in 2017 — and they will be confident of getting their top target this time around as well.
Pep Guardiola
The lure of playing for one of the best coaches in football is surely one of the key components in Kane’s desire to leave.
The Catalan has proved he can win titles by playing an entertaining brand of football, with three Premier League titles in the last four seasons.
That guaranteed success and consistent promise of Champions League football - something that failed to come to fruition under Jose Mourinho - would no doubt satisfy his career goals.
Guardiola has already convinced one Spurs player that the grass certainly is greener at the Etihad Stadium when he secured the signing of Walker four years ago. He wants Kane to replace Sergio Aguero, who left for Barcelona on a free transfer.
It was reported by The Athletic that Kane discussed his decision with a "senior Man City player" on Monday, which suggests the likes of Walker, Raheem Sterling or John Stones may have a role to play in what happens next.
And Guardiola will be hoping that the trio will help put across the idea to Kane that his long-term future belongs in Manchester.
Mauricio Pochettino
The chances of Kane reuniting with his former boss Mauricio Pochettino look remote at this point, but not impossible.
Paris Saint-Germain can already boast to having a wealth of talent available in Kylian Mbappe, Neymar and Angel Di Maria. It means even their central striker Mauro Icardi finds game time difficult to come by at the Parc des Princes.
Kane would have been one of the strong advocates for Pochettino’s mooted return when Levy sacked Mourinho in April but PSG refused to allow him to return.
The pair shared a close working relationship during the Argentine’s five-year reign in north London and it would not be a huge surprise to see Kane link up with him in France, although the fee would almost certainly put him out of the French giants’ reach.
Pochettino’s views on loyalty may be skewed when it comes to Levy. He spurned several opportunities to stay with Spurs, including the Real Madrid job in 2018.
But having led the team to their first-ever Champions League final in May 2019, he was unceremoniously sacked just five months later.
If his advice still holds any weight, he may be telling Kane to grab his chance while it is still there for the taking.
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