Tottenham Hotspur chairman Daniel Levy loves a deadline day deal. There are few protagonists in football more adept at the brinkmanship created by the final hours of a transfer window, often able to extract maximum value from a departing player or grab a last-minute bargain to boost the squad.
Some of Levy's moves occupy a place in football folklore: the 2008 exit of Dimitar Berbatov to Manchester United for £30.75 million, the £8m steal of Rafael van der Vaart from Real Madrid in 2010, the then-world record £86.3m fee Madrid paid to sign Gareth Bale in 2013.
A decade has almost passed since Bale traded north London for the Spanish capital; a tiresome transfer saga which concluded on Sept. 1's deadline day after acrimony between the clubs and the Welshman repeatedly trying to force through a move he feared was doomed to collapse. Levy enhanced his reputation as a fearsome negotiator and improved the financial package on offer with the delay, but any repeat approach with star striker Harry Kane this summer would be a mistake.
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With a contract that expires in 2024, Kane will discuss his future with the club at the end of the season. At the moment, sources have told ESPN that Spurs do not want to let their all-time record goal scorer leave, but there is no suggestion yet that the 29-year-old will sign an extension and the club's hand may be forced.
Sitting nine points behind fourth-placed Manchester United (who have two games in hand), Champions League qualification is all but beyond them and another season of transition next year appears inevitable. There is currently no permanent head coach after the sacking of Antonio Conte, no director of football (after Fabio Paratici resigned when his 30-month ban from his time at Juventus was extended worldwide by FIFA), and the squad is badly in need of upgrades both in defence and midfield.
An early decision over Kane, communicated efficiently and decisively, is essential for all parties to move forward. If Tottenham refuse to let him go, they should issue a statement to that effect and confirm on the record that they will force him to honour the final 12 months of the six-year, £200,000-a-week deal he signed in 2018. But if Kane states his desire to leave and Spurs opt to grant his exit, they must not allow the situation to drag on all summer.
Of course, Tottenham would expect to receive a hefty transfer fee for one of the best strikers in the world at the peak of his powers. When Kane informed the club of his desire to join Manchester City in summer 2021, Spurs held out for £150m and no offers arrived.
Now City have the 50-goal Erling Haaland up front, Manchester United are the most logical destination in England, although it will be intriguing to see if ex-Tottenham boss Mauricio Pochettino tries to convince big-spending Chelsea to enter the running should his appointment as head coach at Stamford Bridge be finalised. Real Madrid, Bayern Munich and Paris Saint-Germain have also previously been linked with Kane.
While he is reportedly keen to stay in England, Spurs would no doubt prefer to let him join an overseas club to help distance them from the damage, just as was the case with Bale and Luka Modric (who moved to Real Madrid in 2012 for around £30m.) Yet Tottenham must also acknowledge the diminishing effect on Kane's transfer valuation given they will only have a one-year insurance policy against losing him for nothing in summer 2024.
Levy was the first Premier League chairman to talk openly about the damaging financial effects of the COVID-19 pandemic and the club estimate a £200m loss of income as a result. Spurs were one of the hardest hit given they had just opened a £1 billion stadium designed to transform their revenue through large-scale multi-sport and music events a year before mass gatherings were restricted across the world.
Last summer, Tottenham owners ENIC invested £150m by way of a capital increase to fund their transfer plans, a short-term move taken in response to pressure from former head coach Conte to show greater ambition in the market. With that cash they signed forward Richarlison (£60m), centre-back Cristian Romero (£50m), midfielder Yves Bissouma (£25m) and right-back Djed Spence (£19m.)
The club's last year-end accounts to June 30, 2022 showed a loss of £50.1m. Tottenham are not under imminent pressure to move Kane on to balance the books, but the decision whether to potentially allow a player whose transfer could fetch £100m to leave for free in 2024, for the sake of retaining him for another 12 months, needs serious financial consideration.
Moreover, Kane already feels slighted by the events of 2021. The striker believed he had a "gentlemen's agreement" with Levy to leave the club, with City ready to pay £100m -- and perhaps more. Spurs sources denied any such agreement existed and City went on to win the 2021-22 Premier League without a recognised centre-forward. Then they signed Haaland from Borussia Dortmund for £52m.
Kane is desperate to win silverware but even as he saw a move which practically guaranteed trophies slipping from his grasp, he stopped short of pressing the nuclear button in 2021. While he failed to report back for the start of preseason, he eventually reintegrated with the group and resumed the professionalism which has otherwise been the byword of his career.
Watching him of late is a reminder of how his individual pursuit of greatness has become more detached from the possibility of any collective success. Spurs were thrashed 6-1 at Newcastle but Kane still scored; he registered two assists as a top-four place slipped further from their grasp in a 2-2 draw at home to Man United; then he tied Wayne Rooney on 208 goals as the Premier League's second-highest scorer of all-time in Sunday's chaotic 4-3 defeat at Liverpool, which effectively ended their Champions League qualification hopes for another year.
He can't give the club anything more. Tottenham supporters would obviously be devastated if Kane left, but at this point of his career most of them would at least understand -- though a move to Old Trafford does not appear the same shortcut to silverware that joining City was in 2021.
Regardless of what comes next, a quick resolution is necessary. The new manager, whoever they are, can use the £100m-plus from Kane's transfer fee to identify and acquire players in a fresh mould, rather than clinging to the carcass of the Pochettino era as Spurs have done for years. Once again, the exit of Bale serves as a warning. Before allowing him to join Real Madrid, Spurs signed seven players knowing the money was coming: Christian Eriksen, Nacer Chadli, Erik Lamela, Paulinho, Etienne Capoue, Vlad Chiriches, Roberto Soldado. Only Eriksen -- and maybe at a push Lamela -- is a signing which stands the test of time.
Trying to replace quality with quantity is a dangerous road. At least in Richarlison, Spurs already have a centre-forward of repute to fill the void left by Kane, though Aston Villa's Ollie Watkins or Roma's Tammy Abraham could be intriguing alternatives. Whatever the strategy, another long game of brinkmanship by Levy feels like too high a price this time and the club, and Kane, need to know where they stand as summer begins.